NaHSO /SiO catalyzed generation of o-quinone/o-thioquinone … · 2020. 10. 8. · 5 Figure 1:...
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1 NaHSO 4 /SiO 2 catalyzed generation of o-quinone/o-thioquinone methides: Synthesis of arylxanthenes/arylthioxanthenes via oxa-6π-electrocyclization Muthupandi Karthick, a Edwin Konikkara Abi, a Nagamalla Someshwar, a Savarimuthu Philip Anthony, b Chinnasamy Ramaraj Ramanathan a * a Department of Chemistry, Pondicherry University, Puducherry – 605 014, India. b School of Chemical & Biotechnology, SASTRA Deemed University, Thanjavur – 613 401. Email: [email protected], Fax: +91-413-2655987; Tel: +91-413-2654416 Table of contents S. No. Title Pages 1 Scheme 1: Synthesis of symmetrical ortho-(hydroxyldiarylmethyl)arene-2-ol derivatives, 2aa-2ch 2 2 Scheme 2: Synthesis of compound 4 & 5 2 3 Scheme 3: Synthesis of unsymmetrical ortho-(hydroxyldiarylmethyl)arene-2-ol derivatives, 6aa-6bi 3 4 Scheme 4: Synthesize of (2-mercaptophenyl)diarylmethanol derivatives, 8a-8f 4 5 Copies of NMR spectra 5-166 6 Absorption and Fluorescence Spectra (Fig. S1, S2, S3 and S4) 167-169 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is © The Royal Society of Chemistry 2020
Transcript of NaHSO /SiO catalyzed generation of o-quinone/o-thioquinone … · 2020. 10. 8. · 5 Figure 1:...
1
NaHSO4/SiO2 catalyzed generation of o-quinone/o-thioquinone methides:
Synthesis of arylxanthenes/arylthioxanthenes via oxa-6π-electrocyclization
Muthupandi Karthick,a Edwin Konikkara Abi,
a Nagamalla Someshwar,
a Savarimuthu Philip Anthony,
b
Chinnasamy Ramaraj Ramanathana*
aDepartment of Chemistry, Pondicherry University, Puducherry – 605 014, India.
bSchool of Chemical & Biotechnology, SASTRA Deemed University, Thanjavur – 613 401.
Email: [email protected], Fax: +91-413-2655987; Tel: +91-413-2654416
Table of contents
S. No. Title Pages
1 Scheme 1: Synthesis of symmetrical ortho-(hydroxyldiarylmethyl)arene-2-ol derivatives, 2aa-2ch 2
2 Scheme 2: Synthesis of compound 4 & 5 2
3 Scheme 3: Synthesis of unsymmetrical ortho-(hydroxyldiarylmethyl)arene-2-ol derivatives, 6aa-6bi 3
4 Scheme 4: Synthesize of (2-mercaptophenyl)diarylmethanol derivatives, 8a-8f 4
5 Copies of NMR spectra 5-166
6 Absorption and Fluorescence Spectra (Fig. S1, S2, S3 and S4) 167-169
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2020
2
Scheme 1: Synthesis of symmetrical ortho-(hydroxyldiarylmethyl)arene-2-ol derivatives, 2aa-2ch18
Scheme 2: Synthesis of compound 4 & 5
3
Scheme 3: Synthesis of unsymmetrical ortho-(hydroxyldiarylmethyl)arene-2-ol derivatives, 6aa-6bi
4
Scheme 4: Synthesis of (2-mercaptophenyl)diarylmethanol derivatives, 8a-8f
5
Figure 1: 1H-NMR spectra for compound 3aa
11 10 9 8 7 6 5 4 3 2 1 ppm
5.311
6.887
6.891
6.907
6.923
6.927
7.000
7.019
7.092
7.112
7.130
7.147
7.160
7.178
7.200
7.203
7.221
7.223
7.282
7.300
7.318
7.319
7.451
7.464
7.546
7.567
7.652
7.673
0.9
9
0.9
9
0.9
88.1
2
1.0
6
1.9
3
1.0
2
1.0
0
Current Data Parameters
NAME MK-ED-28EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190306
Time 10.58INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zg30TD 65536
SOLVENT CDCl3NS 16
DS 2
SWH 8223.685 HzFIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 406DW 60.800 usec
DE 6.00 usec
TE 293.8 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1HP1 14.35 usec
PL1 -1.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300609 MHz
WDW EMSSB 0
LB 0.30 Hz
GB 0PC 1.00
PROTON CDCL3-M.KARTHICK
6
Figure 1a: 1H-NMR spectra expansion for compound 3aa
6.856.906.957.007.057.107.157.207.257.307.357.407.457.507.557.607.657.707.75 ppm
6.887
6.891
6.907
6.923
6.927
7.000
7.019
7.092
7.112
7.130
7.147
7.160
7.178
7.200
7.203
7.221
7.223
7.282
7.300
7.318
7.319
7.451
7.464
7.546
7.567
7.652
7.673
0.9
9
0.9
8
8.1
2
1.0
6
1.9
3
1.0
2
1.0
0
PROTON CDCL3-M.KARTHICK
7
Figure 2: 13C-NMR spectra for compound 3aa
Current Data Parameters
NAME MK-ED-28EXPNO 2
PROCNO 1
F2 - Acquisition ParametersDate_ 20190306
Time 11.12INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 256DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 secRG 362
DW 20.800 usecDE 6.00 usec
TE 294.3 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========NUC1 13C
P1 9.15 usecPL1 0 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG[2 waltz16
NUC2 1HPCPD2 90.00 usec
PL12 14.90 dBPL13 14.90 dB
PL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127604 MHz
WDW EMSSB 0
LB 1.00 HzGB 0
PC 1.40
C13CPD CDCL3-M.KARTHICK
180 160 140 120 100 80 60 40 20 ppm
45.063
76.841
77.159
77.477
112.016
116.780
123.336
124.464
124.909
126.337
126.734
126.936
127.603
128.146
128.497
128.898
128.962
129.691
130.457
133.435
146.200
149.908
151.541
8
Figure 3: 1H-NMR spectra for compound 3ab
11 10 9 8 7 6 5 4 3 2 1 ppm3.769
3.832
5.326
6.602
6.608
6.623
6.629
6.760
6.766
6.824
6.845
6.978
7.000
7.149
7.170
7.260
7.301
7.303
7.321
7.338
7.341
7.394
7.396
7.414
7.431
7.434
7.543
7.551
7.662
7.682
7.765
7.785
3.0
13.0
7
0.9
7
1.0
0
1.0
02.0
2
1.0
1
1.9
9
1.0
5
1.0
31.9
7
1.0
0
1.0
3
Current Data Parameters
NAME MK-ED-5EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20180803
Time 10.29INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zg30TD 65536
SOLVENT CDCl3
NS 16DS 2
SWH 8223.685 Hz
FIDRES 0.125483 HzAQ 3.9845889 sec
RG 144
DW 60.800 usecDE 6.00 usec
TE 292.8 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usec
PL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768
SF 400.1300046 MHzWDW EM
SSB 0
LB 0.30 HzGB 0
PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
9
Figure 3: 1H-NMR spectra for compound 3ab
6.66.76.86.97.07.17.27.37.47.57.67.77.87.9 ppm
6.602
6.608
6.623
6.629
6.760
6.766
6.824
6.845
6.978
7.000
7.149
7.170
7.260
7.301
7.303
7.321
7.338
7.341
7.394
7.396
7.414
7.431
7.434
7.543
7.551
7.662
7.682
7.765
7.785
1.0
0
1.0
0
2.0
2
1.0
1
1.9
9
1.0
5
1.0
3
1.9
7
1.0
0
1.0
3
PROTON CDCl3 {D:\CRR} KOPAL 1
10
Figure 4: 13C-NMR spectra for compound 3ab
Current Data ParametersNAME MK-ED-5
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20180803Time 10.33
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usecTE 293.0 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.95 usec
PL1 -1.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6127593 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
43.512
55.338
55.560
76.843
77.160
77.478
101.438
110.177
111.866
114.253
117.281
124.429
126.266
126.889
127.219
127.590
128.877
129.508
130.230
130.438
133.301
138.805
149.843
152.159
158.394
159.519
11
Figure 5: 1H-NMR spectra for compound 3ac
12 11 10 9 8 7 6 5 4 3 2 1 ppm
2.313
2.374
5.370
6.834
6.837
6.854
6.856
6.996
7.015
7.043
7.095
7.115
7.140
7.145
7.160
7.260
7.300
7.303
7.317
7.320
7.323
7.337
7.340
7.396
7.399
7.413
7.416
7.420
7.434
7.437
7.566
7.666
7.687
7.769
7.790
3.0
0
3.0
0
0.9
9
1.0
9
2.0
9
4.0
9
1.1
0
1.2
8
1.9
5
1.0
7
1.0
0
Current Data ParametersNAME MK-XN-N4EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190105Time 10.19INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 161DW 60.800 usecDE 6.00 usecTE 293.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300048 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} nmr 1
12
Figure 5a: 1H-NMR spectra expansion for compound 3ac
6.97.07.17.27.37.47.57.67.77.8 ppm
6.834
6.837
6.854
6.856
6.996
7.015
7.043
7.095
7.115
7.140
7.145
7.160
7.260
7.300
7.303
7.317
7.320
7.323
7.337
7.340
7.396
7.399
7.413
7.416
7.420
7.434
7.437
7.566
7.666
7.687
7.769
7.790
1.0
9
2.0
9
4.0
9
1.1
0
1.2
8
1.9
5
1.0
7
1.0
0
PROTON CDCl3 {D:\CRR} nmr 1
13
Figure 6: 13C-NMR spectra for compound 3ac
Current Data Parameters
NAME MK-XN-N4EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190106
Time 13.40INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 362DW 20.800 usec
DE 6.00 usec
TE 290.4 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127612 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} nmr 1
180 160 140 120 100 80 60 40 20 ppm
21.15
21.26
44.30
76.84
77.16
77.48
111.90
117.05
122.02
124.24
124.33
126.22
126.87
127.07
127.59
128.31
128.84
129.34
129.60
130.39
133.36
136.35
138.13
143.57
149.99
151.26
14
11 10 9 8 7 6 5 4 3 2 1 ppm
3.249
3.258
6.681
6.683
6.702
6.703
7.014
7.098
7.101
7.117
7.190
7.192
7.210
7.213
7.260
7.268
7.273
7.282
7.286
7.290
7.293
7.299
7.316
7.319
7.328
7.332
7.348
7.352
7.420
7.423
7.573
7.679
7.699
7.777
7.797
7.827
8.029
8.033
8.048
8.053
1.02
2.92
0.99
1.00
1.03
0.97
0.32
0.57
1.69
1.33
1.03
1.02
1.01
1.00
0.96
1.00
Current Data Parameters
NAME MK-II-429
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190612Time 13.01
INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 16DS 2
SWH 8223.685 Hz
FIDRES 0.125483 Hz
AQ 3.9845889 sec
RG 203
DW 60.800 usec
DE 6.00 usecTE 295.0 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 14.35 usecPL1 -1.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300094 MHz
WDW EMSSB 0
LB 0.30 Hz
GB 0
PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 7: 1H-NMR spectra for compound 3ad
15
Figure 7a: 1H-NMR spectra expansion for compound 3ad
6.76.86.97.07.17.27.37.47.57.67.77.87.98.08.1 ppm
6.681
6.683
6.702
6.703
6.996
7.014
7.030
7.033
7.082
7.098
7.101
7.117
7.120
7.190
7.192
7.210
7.213
7.243
7.247
7.260
7.268
7.273
7.279
7.282
7.286
7.290
7.293
7.299
7.316
7.319
7.328
7.332
7.348
7.352
7.399
7.402
7.416
7.420
7.423
7.573
7.679
7.699
7.777
7.797
7.827
8.029
8.033
8.048
8.053
0.9
9
1.0
0
1.0
3
0.9
7
0.3
2
0.5
7
1.6
9
1.3
3
1.0
3
1.0
2
1.0
1
1.0
0
0.9
6
1.0
0
16
Current Data Parameters
NAME MK-II-429EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190620
Time 13.07INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 293.3 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127599 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
55.55
69.27
76.84
77.16
77.47
110.94
112.54
115.96
120.46
122.85
124.12
125.63
126.57
126.76
127.03
127.77
128.10
128.90
129.04
129.57
130.06
133.77
136.32
148.82
150.39
155.80
Figure 8: 13C-NMR spectra for compound 3ad
17
Figure 9: 1H-NMR spectra for compound 3ae
11 10 9 8 7 6 5 4 3 2 1 ppm
2.180
2.712
5.729
6.882
6.900
7.003
7.014
7.020
7.025
7.027
7.105
7.113
7.116
7.121
7.129
7.134
7.136
7.142
7.145
7.153
7.182
7.201
7.221
7.260
7.298
7.301
7.304
7.318
7.321
7.362
7.365
7.379
7.382
7.385
7.527
7.666
7.687
7.707
7.721
7.742
2.9
6
2.9
4
1.0
0
0.9
6
1.8
9
2.9
51.0
1
1.0
0
0.9
8
0.9
5
1.0
00.9
4
1.0
2
Current Data ParametersNAME MK-II-407EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190424Time 18.50INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 203DW 60.800 usecDE 6.00 usecTE 293.9 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300093 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
18
Figure 9a: 1H-NMR spectra expansion for compound 3ae
6.97.07.17.27.37.47.57.67.77.8 ppm
6.882
6.900
7.003
7.014
7.020
7.025
7.027
7.105
7.113
7.116
7.121
7.129
7.134
7.136
7.142
7.145
7.153
7.182
7.201
7.221
7.260
7.281
7.284
7.298
7.301
7.304
7.318
7.321
7.362
7.365
7.379
7.382
7.385
7.399
7.402
7.527
7.666
7.687
7.707
7.721
7.742
0.9
6
1.8
9
2.9
5
1.0
1
1.0
0
0.9
8
0.9
5
1.0
1
0.9
3
1.0
2
PROTON CDCl3 {D:\CRR} CIF_NMR 1
19
Figure 10: 13C-NMR spectra for compound 3ae
Current Data ParametersNAME MK-II-407
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20190424Time 22.37
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 147
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usecTE 293.5 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.95 usec
PL1 -1.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6127628 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
19.669
20.346
39.149
76.839
77.158
77.475
112.018
114.639
123.823
124.311
125.168
126.160
126.451
126.871
126.966
127.413
127.534
127.709
127.862
129.407
130.421
130.958
133.326
133.785
137.603
144.325
149.402
152.322
20
Figure 11: 1H-NMR spectra for compound 3af
11 10 9 8 7 6 5 4 3 2 1 ppm
1.544
6.842
7.151
7.169
7.189
7.229
7.232
7.248
7.250
7.260
7.268
7.286
7.302
7.305
7.322
7.324
7.353
7.356
7.370
7.373
7.376
7.390
7.393
7.471
7.493
7.569
7.581
7.591
7.601
7.721
7.740
7.759
7.800
7.823
7.846
7.862
7.869
7.890
8.893
8.915
1.01
1.00
3.46
1.07
1.03
1.06
4.04
2.08
5.31
1.00
Current Data ParametersNAME MK-XN-N4-FEXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190802Time 14.19INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536
SOLVENT CDCl3NS 16DS 2
SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 362
DW 60.800 usecDE 6.00 usecTE 294.5 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usec
PL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300095 MHzWDW EM
SSB 0LB 0.30 HzGB 0
PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
21
Figure 11a: 1H-NMR spectra expansion for compound 3af
6.97.07.17.27.37.47.57.67.77.87.9 ppm
6.842
7.151
7.169
7.189
7.229
7.232
7.248
7.250
7.260
7.268
7.286
7.302
7.305
7.322
7.324
7.339
7.342
7.353
7.356
7.370
7.373
7.376
7.390
7.393
7.471
7.493
7.569
7.581
7.591
7.601
7.721
7.740
7.759
7.778
7.781
7.800
7.823
7.846
7.862
7.869
7.890
1.0
1
1.0
0
3.4
6
1.0
7
1.0
3
1.0
6
4.0
4
2.0
8
5.3
1
22
Figure 12: 13C-NMR spectra for compound 3af
Current Data Parameters
NAME MK-XN-N4-FEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190805
Time 10.11INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 1024
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 294.1 KD1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1HPCPD2 90.00 usec
PL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127579 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
36.095
76.841
77.158
77.476
112.332
116.708
118.165
122.983
123.121
124.244
124.426
125.709
126.236
126.710
126.728
126.881
127.074
127.205
127.505
127.713
128.012
128.709
129.334
129.591
130.375
130.489
130.836
132.035
133.271
134.335
143.273
148.566
23
Figure 13: 1H-NMR spectra for compound 3ag
234567891011 ppm
1.559
5.384
6.745
6.751
6.772
6.912
6.919
6.936
6.943
6.962
6.979
6.984
6.989
7.001
7.005
7.017
7.018
7.022
7.024
7.038
7.170
7.183
7.192
7.205
7.260
7.335
7.338
7.341
7.355
7.358
7.409
7.412
7.429
7.432
7.511
7.561
7.662
7.683
7.767
7.788
0.9
8
0.9
9
0.9
3
2.9
71.9
8
1.0
1
1.0
0
0.9
9
0.9
91.0
0
1.0
0
Current Data Parameters
NAME MK-II-400EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190422
Time 12.38INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zg30TD 65536
SOLVENT CDCl3
NS 16DS 2
SWH 8223.685 Hz
FIDRES 0.125483 HzAQ 3.9845889 sec
RG 456
DW 60.800 usecDE 6.00 usec
TE 292.6 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 14.35 usecPL1 -1.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300093 MHzWDW EM
SSB 0
LB 0.30 HzGB 0
PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
24
Figure 13a: 1H-NMR spectra expansion for compound 3ag
6.76.86.97.07.17.27.37.47.57.67.77.8 ppm
6.723
6.730
6.745
6.751
6.765
6.772
6.912
6.919
6.936
6.943
6.962
6.979
6.984
6.989
7.001
7.005
7.017
7.018
7.022
7.024
7.038
7.040
7.170
7.183
7.192
7.205
7.260
7.318
7.321
7.335
7.338
7.341
7.355
7.358
7.409
7.412
7.426
7.429
7.432
7.446
7.449
7.511
7.561
7.662
7.683
7.767
7.788
0.9
9
0.9
3
2.9
7
1.9
8
1.0
1
1.0
0
0.9
9
0.9
9
1.0
0
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
25
Figure 14: 13C-NMR spectra for compound 3ag
Current Data Parameters
NAME MK-II-400EXPNO 2
PROCNO 1
F2 - Acquisition ParametersDate_ 20190423
Time 10.22INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zgpg30
TD 65536SOLVENT CDCl3
NS 256DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 secRG 256
DW 20.800 usecDE 6.00 usec
TE 291.5 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG[2 waltz16
NUC2 1HPCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dBSFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127591 MHz
WDW EMSSB 0
LB 1.00 HzGB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm43.703
76.841
77.159
77.476
104.064
104.312
110.561
110.778
112.217
115.793
116.006
120.506
120.539
124.810
126.043
126.607
127.009
127.591
128.927
129.937
130.016
130.546
130.589
130.684
133.377
141.786
141.819
149.247
152.086
152.208
160.601
161.032
26
Figure 15: 1H-NMR spectra for compound 3ah
11 10 9 8 7 6 5 4 3 2 1 ppm
5.263
6.899
7.048
7.069
7.132
7.164
7.185
7.233
7.251
7.261
7.269
7.324
7.343
7.361
7.407
7.469
7.568
7.588
7.675
7.695
1.0
0
1.9
6
1.9
8
3.2
0
1.2
8
0.9
1
1.0
91.0
6
1.1
2
1.0
7
Current Data ParametersNAME MK-ED-42EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190301Time 22.35INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 812DW 60.800 usecDE 6.00 usecTE 293.9 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300458 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
27
Figure 15a: 1H-NMR spectra expansion for compound 3ah
6.97.07.17.27.37.47.57.67.77.8 ppm
6.899
7.048
7.069
7.132
7.164
7.185
7.233
7.251
7.261
7.269
7.324
7.343
7.361
7.407
7.469
7.568
7.588
7.675
7.695
1.9
6
1.9
8
3.2
0
1.2
8
0.9
1
1.0
9
1.0
6
1.1
2
1.0
7
28
Figure 16: 13C-NMR spectra for compound 3ah
Current Data Parameters
NAME MK-ED-42-AEXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190320
Time 19.30INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 512
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 297.5 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127558 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
43.972
76.844
77.162
77.479
112.378
117.212
122.972
123.666
124.892
125.534
126.701
127.028
127.609
127.931
128.814
128.940
129.258
129.828
130.529
130.585
133.028
133.479
133.580
144.204
149.197
151.945
29
Figure 17: 1H-NMR spectra for compound 3ai
11 10 9 8 7 6 5 4 3 2 1 ppm
5.514
7.189
7.209
7.260
7.276
7.296
7.342
7.363
7.386
7.442
7.461
7.479
7.503
7.530
7.557
7.577
7.610
7.682
7.702
7.793
7.813
0.9
9
0.9
6
0.9
6
2.9
81.0
4
1.9
5
1.9
9
0.9
4
1.0
3
1.0
0
Current Data ParametersNAME MK-ED-39EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190212Time 10.50INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 181DW 60.800 usecDE 6.00 usecTE 292.6 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300093 MHzWDW EMSSB 0
LB 0.30 HzGB 0PC 1.00
PROTON CDCL3
30
Figure 17a: 1H-NMR spectra expansion for compound 3ai
7.207.257.307.357.407.457.507.557.607.657.707.757.807.85 ppm
7.189
7.209
7.260
7.276
7.296
7.342
7.363
7.386
7.442
7.461
7.479
7.503
7.530
7.557
7.577
7.610
7.682
7.702
7.793
7.813
0.9
6
0.9
6
2.9
8
1.0
4
1.9
5
1.9
9
0.9
4
1.0
3
1.0
0
PROTON CDCL3
31
Figure 18: 13C-NMR spectra for compound 3ai
Current Data Parameters
NAME MK-ED-39AEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190322
Time 7.38INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 167
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 912DW 20.800 usec
DE 6.00 usec
TE 295.5 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127570 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
44.744
76.844
77.161
77.479
112.604
114.476
114.517
120.002
120.038
122.437
122.779
124.661
125.120
126.192
126.229
126.266
126.936
127.112
127.637
127.718
128.762
129.028
129.749
130.264
130.676
130.858
131.186
133.605
149.013
151.500
32
10 9 8 7 6 5 4 3 2 1 ppm
5.141
6.843
6.846
6.862
6.864
6.865
6.880
6.883
6.937
6.954
7.019
7.022
7.040
7.043
7.075
7.080
7.084
7.088
7.093
7.096
7.101
7.113
7.117
7.142
7.147
7.160
7.178
7.180
1.0
0
2.0
92.0
3
2.0
1
5.0
3
2.1
0
Current Data ParametersNAME MK-XN-M1EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190102Time 10.31INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 114DW 60.800 usecDE 6.00 usecTE 289.8 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300673 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} nmr 1
Figure 19: 1H-NMR spectra for compound 3ba
33
Current Data Parameters
NAME MK-XN-M1EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190102
Time 10.48INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3
NS 256DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 406DW 20.800 usec
DE 6.00 usec
TE 290.0 KD1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1HPCPD2 90.00 usec
PL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127642 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} nmr 1
180 160 140 120 100 80 60 40 20 ppm
44.481
76.844
77.162
77.480
116.656
123.336
124.503
126.764
128.001
128.506
128.862
129.845
146.589
151.113
Figure 20: 13C-NMR spectra for compound 3ba
34
234567891011 ppm
3.767
3.811
5.166
6.573
6.580
6.595
6.601
6.689
6.696
6.814
6.819
6.831
6.836
6.843
6.929
6.930
6.950
6.952
6.983
6.986
7.000
7.004
7.042
7.043
7.045
7.061
7.065
7.101
7.108
7.114
7.125
7.130
7.134
7.186
7.190
7.204
7.207
7.223
7.224
7.228
2.7
9
2.9
2
0.9
4
0.9
2
0.9
2
1.8
1
0.9
2
0.9
80.9
6
2.7
6
1.0
0
Current Data ParametersNAME MK-ED-45EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190318Time 14.54INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 128DW 60.800 usecDE 6.00 usecTE 294.7 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300091 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 21: 1H-NMR spectra for compound 3bb
35
Current Data Parameters
NAME MK-ED-45EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190318
Time 15.01INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 101
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 645DW 20.800 usec
DE 6.00 usec
TE 294.9 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127608 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
20406080100120140160180 ppm
42.99
55.31
55.51
76.84
77.16
77.47
101.22
110.31
114.17
116.52
116.94
123.30
125.01
127.80
129.47
129.89
130.41
139.28
151.00
151.75
158.33
159.38
Figure 22: 13C-NMR spectra for compound 3bb
36
12345678910 ppm2.468
2.506
5.365
6.961
6.962
6.981
6.982
7.097
7.117
7.122
7.129
7.137
7.139
7.140
7.155
7.158
7.217
7.237
7.246
7.260
7.276
7.279
7.297
7.300
7.349
7.353
7.370
7.387
7.391
2.8
93.0
3
1.0
2
1.0
0
3.0
1
1.0
5
5.0
3
1.0
3
Current Data ParametersNAME MK-XN-M4EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190104Time 12.26INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 228DW 60.800 usecDE 6.00 usecTE 293.9 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1299353 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} nmr 1
Figure 23: 1H-NMR spectra for compound 3bc
37
Current Data Parameters
NAME MK-XN-M4EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190104
Time 12.42INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 220
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 45.2DW 20.800 usec
DE 6.00 usec
TE 294.2 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127570 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} nmr 1
20406080100120140160180 ppm
21.14
21.22
43.79
76.84
77.16
77.47
116.61
116.94
121.69
123.20
124.28
124.86
127.83
128.36
129.53
129.85
136.25
137.96
143.99
150.91
151.21
Figure 24: 13C-NMR spectra for compound 3bc
38
11 10 9 8 7 6 5 4 3 2 1 ppm
1.532
6.728
6.900
6.903
6.904
6.907
6.919
7.177
7.181
7.194
7.201
7.206
7.222
7.226
7.235
7.243
7.246
7.260
7.278
7.281
7.298
7.300
7.409
7.411
7.429
7.456
7.479
7.591
7.609
7.625
7.685
7.706
7.782
7.803
7.809
7.832
7.891
7.911
8.880
8.902
0.9
9
1.0
75.2
0
1.0
3
1.0
0
0.9
9
2.0
21.0
0
1.9
2
1.0
4
0.9
9
1.0
0
Current Data ParametersNAME MK-XN-M5-FEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190622Time 18.40INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 161DW 60.800 usecDE 6.00 usecTE 293.1 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300095 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 25: 1H-NMR spectra for compound 3bd
39
Figure 25a: 1H-NMR spectra expansion for compound 3bd
6.86.97.07.17.27.37.47.57.67.77.87.9 ppm
6.728
6.883
6.888
6.900
6.903
6.904
6.907
6.919
6.924
7.177
7.181
7.189
7.194
7.201
7.206
7.222
7.226
7.235
7.243
7.246
7.260
7.278
7.281
7.298
7.300
7.315
7.318
7.409
7.411
7.429
7.456
7.479
7.572
7.573
7.591
7.609
7.625
7.685
7.706
7.765
7.768
7.782
7.803
7.809
7.832
7.891
7.911
0.9
9
1.0
7
5.2
0
1.0
3
1.0
0
0.9
9
2.0
2
1.0
0
1.9
2
1.0
4
0.9
9
PROTON CDCl3 {D:\CRR} CIF_NMR 1
40
Current Data Parameters
NAME MK-XN-M5-FEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190622
Time 19.11INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 512
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 36DW 20.800 usec
DE 6.00 usec
TE 293.2 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127608 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm35.86
76.84
77.16
77.48
116.39
116.92
118.08
122.92
123.16
123.22
123.56
124.17
124.91
125.08
125.67
126.30
126.98
127.11
127.20
127.69
127.82
128.59
128.62
129.25
129.52
129.61
130.41
130.51
130.88
132.05
134.18
143.57
149.78
Figure 26: 13C-NMR spectra for compound 3bd
41
Figure 27: 1H-NMR spectra for compound 3ch
10 9 8 7 6 5 4 3 2 1 ppm2.354
5.175
6.828
6.831
6.848
6.850
6.851
6.886
6.906
6.929
6.949
6.960
6.965
6.981
6.986
7.109
7.114
7.125
7.130
7.156
7.160
7.248
7.255
7.260
7.271
7.276
7.281
3.1
3
1.0
0
1.0
1
1.0
2
1.0
2
1.7
9
1.8
5
0.9
2
0.9
5
1.0
0
Current Data ParametersNAME MK-II-387EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190403Time 11.32INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 228DW 60.800 usecDE 6.00 usecTE 294.5 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300009 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
42
Figure 27a: 1H-NMR spectra expansion for compound 3ch
6.806.856.906.957.007.057.107.157.207.257.307.35 ppm
6.828
6.831
6.848
6.850
6.851
6.886
6.906
6.929
6.949
6.960
6.965
6.981
6.986
7.109
7.114
7.125
7.130
7.156
7.160
7.248
7.255
7.260
7.271
7.276
7.281
1.0
1
1.0
2
1.0
2
1.7
9
1.8
5
0.9
2
0.9
5
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
43
Current Data Parameters
NAME MK-II-387EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190403
Time 18.39INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 1024
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 45.2DW 20.800 usec
DE 6.00 usec
TE 297.6 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127572 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
21.21
43.17
76.84
77.16
77.48
117.06
117.13
120.51
122.73
123.58
124.83
129.12
129.43
129.77
130.75
132.82
133.33
138.62
144.86
150.41
151.62
Figure 28: 13C-NMR spectra for compound 3ch
44
Figure 29: 1H-NMR spectra for compound 7aa
13 12 11 10 9 8 7 6 5 4 3 2 1 ppm
3.832
5.377
6.598
6.605
6.620
6.626
6.764
6.771
6.988
7.009
7.181
7.185
7.189
7.197
7.203
7.220
7.224
7.234
7.245
7.251
7.255
7.260
7.273
7.292
7.310
7.314
7.317
7.335
7.337
7.393
7.395
7.413
7.430
7.433
7.557
7.657
7.678
7.764
7.785
3.0
3
1.0
4
0.9
8
0.9
61.0
0
0.7
5
1.0
2
1.3
8
1.9
71.1
8
1.0
7
2.0
6
1.0
3
1.0
0
Current Data ParametersNAME MK-ED-47EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190320Time 12.53INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 161
DW 60.800 usecDE 6.00 usecTE 295.7 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dB
SFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300092 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
45
Figure 29: 1H-NMR spectra for compound 7aa
6.76.86.97.07.17.27.37.47.57.67.77.8 ppm
6.598
6.605
6.620
6.626
6.764
6.771
6.988
7.009
7.181
7.185
7.189
7.197
7.203
7.220
7.224
7.234
7.245
7.251
7.255
7.260
7.273
7.292
7.310
7.314
7.317
7.335
7.337
7.393
7.395
7.413
7.430
7.433
7.557
7.657
7.678
7.764
7.785
0.9
8
0.9
6
1.0
0
0.7
5
1.0
2
1.3
8
1.9
7
1.1
8
1.0
7
2.0
6
1.0
3
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
46
Figure 30: 13C-NMR spectra for compound 7aa
Current Data Parameters
NAME MK-ED-47AEXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190320
Time 23.56INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3
NS 101DS 4
SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 724DW 20.800 usec
DE 6.00 usec
TE 298.3 KD1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13C
P1 9.95 usec
PL1 -1.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG[2 waltz16
NUC2 1H
PCPD2 90.00 usecPL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127634 MHzWDW EM
SSB 0
LB 1.00 HzGB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
44.417
55.527
76.840
77.158
77.475
101.519
110.226
111.933
116.962
124.452
126.305
126.773
126.847
126.902
127.589
128.456
128.911
128.971
130.282
130.454
133.368
146.594
149.811
152.182
159.618
47
Figure 31: 1H-NMR spectra for compound 7ab
13 12 11 10 9 8 7 6 5 4 3 2 1 ppm
3.810
5.084
6.891
6.897
7.000
7.006
7.021
7.027
7.114
7.167
7.171
7.185
7.190
7.260
7.280
7.289
7.294
7.299
7.304
7.313
7.486
7.490
7.496
7.503
7.509
7.516
7.520
7.792
7.797
7.808
7.815
8.272
8.294
8.672
8.690
8.695
3.3
1
1.1
0
1.0
9
1.1
8
1.1
0
2.3
6
3.8
4
2.3
4
1.1
2
1.1
0
1.1
0
Current Data ParametersNAME MK-II-403EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190424Time 10.50INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 256DW 60.800 usecDE 6.00 usecTE 297.5 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300092 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
48
Figure 31a: 1H-NMR spectra expansion for compound 7ab
6.86.97.07.17.27.37.47.57.67.77.87.98.08.18.28.38.48.58.68.78.8 ppm
6.891
6.897
7.000
7.006
7.021
7.027
7.114
7.167
7.171
7.185
7.190
7.260
7.280
7.289
7.294
7.299
7.304
7.313
7.486
7.490
7.496
7.503
7.509
7.516
7.520
7.792
7.797
7.808
7.815
8.272
8.294
8.672
8.690
8.695
1.0
9
1.1
8
1.1
0
2.3
6
3.8
4
2.3
4
1.1
2
1.1
0
1.1
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
49
Current Data Parameters
NAME MK-I-403EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190424
Time 19.23INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 129
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 228DW 20.800 usec
DE 6.00 usec
TE 294.3 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127631 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
52.50
55.56
76.84
77.16
77.48
110.00
110.97
113.23
123.84
123.95
124.22
124.99
125.90
127.71
127.82
128.15
129.40
134.52
134.74
135.96
138.29
139.46
150.78
151.27
159.08
Figure 32: 13C-NMR spectra for compound 7ab
50
Figure 33: 1H-NMR spectra for compound 7ac
11 10 9 8 7 6 5 4 3 2 1 ppm
2.270
5.306
6.733
6.735
6.752
6.754
6.891
6.911
6.941
7.015
7.041
7.104
7.121
7.142
7.159
7.163
7.171
7.174
7.192
7.200
7.215
7.218
7.236
7.238
7.295
7.297
7.315
7.318
7.332
7.335
7.464
7.473
7.564
7.585
7.668
2.7
0
1.0
0
0.8
7
0.8
7
0.9
00.9
6
1.5
7
2.4
1
2.1
7
1.1
02.0
5
1.0
3
1.0
9
Current Data ParametersNAME MK-II-396EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190408Time 12.38INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 406DW 60.800 usecDE 6.00 usecTE 294.8 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300450 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
51
Figure 33a: 1H-NMR spectra expansion for compound 7ac
6.76.86.97.07.17.27.37.47.57.67.7 ppm
6.733
6.735
6.752
6.754
6.891
6.911
6.941
7.015
7.041
7.104
7.121
7.142
7.159
7.163
7.171
7.174
7.192
7.200
7.215
7.218
7.236
7.238
7.295
7.297
7.315
7.318
7.332
7.335
7.464
7.473
7.564
7.585
7.668
7.688
0.8
7
0.8
7
0.9
0
0.9
6
1.5
7
2.4
1
2.1
7
1.1
0
2.0
5
1.0
3
1.0
9
PROTON CDCl3 {D:\CRR} CIF_NMR 1
52
Figure 34: 13C-NMR spectra for compound 7ac
Current Data Parameters
NAME MK-II-396EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190408
Time 16.15INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3
NS 256DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 45.2DW 20.800 usec
DE 6.00 usec
TE 294.4 KD1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1HPCPD2 90.00 usec
PL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127624 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
21.262
44.745
76.841
77.159
77.476
111.960
116.725
117.103
121.841
123.304
124.263
124.385
126.277
126.779
126.890
127.588
128.055
128.358
128.457
128.826
128.921
129.390
129.637
130.397
133.409
138.234
146.467
149.988
151.306
53
Figure 35: 1H-NMR spectra for compound 7ad
12 11 10 9 8 7 6 5 4 3 2 1 ppm
2.968
5.353
6.426
6.432
6.447
6.454
6.547
6.553
6.928
6.949
7.166
7.183
7.200
7.204
7.238
7.254
7.282
7.316
7.319
7.376
7.378
7.396
7.399
7.413
7.416
7.539
7.548
7.648
7.669
7.753
7.773
6.0
0
1.0
4
1.0
2
1.0
1
1.0
2
0.9
8
5.2
0
1.0
5
0.9
2
1.0
1
1.0
4
0.9
9
Current Data ParametersNAME MK-II-425 solvedEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190531Time 21.42INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 228DW 60.800 usecDE 6.00 usecTE 291.9 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300095 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
54
Figure 35a: 1H-NMR spectra expansion for compound 7ad
6.46.56.66.76.86.97.07.17.27.37.47.57.67.77.8 ppm
6.426
6.432
6.447
6.454
6.547
6.553
6.928
6.949
7.166
7.183
7.200
7.204
7.238
7.254
7.282
7.316
7.319
7.376
7.378
7.396
7.399
7.413
7.416
7.539
7.548
7.648
7.669
7.753
7.773
1.0
2
1.0
1
1.0
2
0.9
8
5.2
0
1.0
5
0.9
2
1.0
1
1.0
4
0.9
9
PROTON CDCl3 {D:\CRR} CIF_NMR 1
55
Figure 36: 13C-NMR spectra for compound 7ad
180 160 140 120 100 80 60 40 20 ppm
40.71
44.27
76.84
77.16
77.48
99.93
108.46
111.80
112.68
124.27
126.17
126.60
126.86
127.36
127.58
128.49
128.84
128.94
129.99
130.31
133.34
147.05
150.18
150.82
152.14
Current Data Parameters
NAME MK-II-425-A
EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190531
Time 22.26
INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 1024
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 406
DW 20.800 usec
DE 6.00 usec
TE 292.3 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usec
PL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dB
PL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127588 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
56
Figure 37: 1H-NMR spectra for compound 7ae
11 10 9 8 7 6 5 4 3 2 1 ppm
6.025
7.057
7.076
7.094
7.177
7.196
7.215
7.260
7.351
7.354
7.360
7.367
7.378
7.393
7.421
7.470
7.480
7.488
7.502
7.620
7.761
7.770
7.781
7.790
7.827
7.849
7.880
8.020
8.041
0.9
6
0.9
6
2.0
1
5.1
8
2.2
21.0
3
2.0
1
2.0
4
1.0
1
1.0
0
Current Data ParametersNAME MK-II-406EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190425Time 22.37INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 203DW 60.800 usecDE 6.00 usecTE 292.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300093 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
57
Figure 37a: 1H-NMR spectra expansion for compound 7ae
7.17.27.37.47.57.67.77.87.98.08.1 ppm
7.057
7.076
7.094
7.177
7.196
7.215
7.260
7.351
7.354
7.360
7.367
7.378
7.393
7.421
7.470
7.480
7.488
7.502
7.620
7.761
7.770
7.781
7.790
7.827
7.849
7.880
8.020
8.041
0.9
6
2.0
1
5.1
8
2.2
2
1.0
3
2.0
1
2.0
4
1.0
1
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
58
Figure 38: 13C-NMR spectra for compound 7ae
Current Data Parameters
NAME MK-II-406EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190426
Time 7.39INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 74
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 256DW 20.800 usec
DE 6.00 usec
TE 295.0 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127637 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
42.395
76.843
77.161
77.478
112.240
116.284
118.185
123.040
124.273
124.520
126.279
126.672
126.818
126.972
127.002
127.327
127.592
128.435
128.777
129.001
129.289
130.737
130.866
131.761
133.277
146.272
149.055
149.732
59
234567891011 ppm
6.034
7.067
7.085
7.162
7.182
7.200
7.260
7.356
7.358
7.376
7.379
7.408
7.426
7.429
7.542
7.550
7.559
7.561
7.566
7.747
7.751
7.770
7.784
7.788
7.800
7.821
7.916
8.060
8.084
8.664
8.670
8.688
8.700
8.704
8.723
8.732
8.735
8.737
8.751
8.755
1.0
0
1.0
8
2.2
1
1.2
8
3.0
5
2.0
05.4
6
1.0
5
1.0
0
3.3
0
Current Data ParametersNAME MK-II-417-AEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190514Time 10.14INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 362DW 60.800 usecDE 6.00 usecTE 292.0 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300095 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 39: 1H-NMR spectra for compound 7af
60
Figure 39a: 1H-NMR spectra expansion for compound 7af
7.07.17.27.37.47.57.67.77.87.98.08.18.28.38.48.58.68.78.88.9 ppm
7.048
7.067
7.085
7.162
7.182
7.200
7.260
7.356
7.358
7.376
7.379
7.408
7.426
7.429
7.542
7.550
7.559
7.561
7.566
7.747
7.751
7.770
7.784
7.788
7.800
7.821
7.916
8.060
8.084
8.664
8.670
8.688
8.700
8.704
8.723
8.732
8.735
8.737
8.751
8.755
1.0
8
2.2
1
1.2
8
3.0
5
2.0
0
5.4
6
1.0
5
1.0
0
3.3
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
61
Current Data Parameters
NAME MK-II-417-AEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190514
Time 11.59INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 220
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 292.9 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127634 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
20406080100120140160180 ppm
42.473
76.841
77.159
77.476
112.330
112.691
122.650
122.702
123.087
123.737
124.578
124.939
124.962
126.281
126.735
126.823
127.012
127.033
127.270
127.351
127.416
127.629
128.077
128.287
129.018
130.468
130.821
131.007
133.221
145.458
146.012
148.746
Figure 40: 13C-NMR spectra for compound 7af
62
Figure 41: 1H-NMR spectra for compound 7ag
13 12 11 10 9 8 7 6 5 4 3 2 1 ppm
1.467
5.311
6.850
6.872
6.894
6.926
6.943
6.946
6.981
6.997
7.085
7.090
7.098
7.107
7.120
7.133
7.144
7.148
7.151
7.161
7.165
7.181
7.207
7.210
7.227
7.245
7.247
7.300
7.302
7.320
7.337
7.340
7.428
7.471
7.566
7.587
7.664
7.685
0.8
9
1.9
9
0.8
1
0.9
1
3.2
0
1.2
4
1.1
7
1.1
0
0.9
1
1.0
0
0.9
7
1.0
0
Current Data ParametersNAME MK-II-394EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190408Time 12.33INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 181DW 60.800 usecDE 6.00 usecTE 294.9 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300529 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
63
Figure 41a: 1H-NMR spectra expansion for compound 7ag
6.906.957.007.057.107.157.207.257.307.357.407.457.507.557.607.657.707.75 ppm
6.850
6.872
6.894
6.926
6.943
6.946
6.981
6.997
7.085
7.090
7.098
7.107
7.120
7.133
7.144
7.148
7.151
7.161
7.165
7.181
7.207
7.210
7.227
7.245
7.247
7.300
7.302
7.320
7.337
7.340
7.428
7.471
7.566
7.587
7.664
7.685
1.9
9
0.8
1
0.9
1
3.2
0
1.2
4
1.1
7
1.1
0
0.9
1
1.0
0
0.9
7
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
64
Current Data Parameters
NAME MK-II-394EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190408
Time 15.43INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 294.4 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127588 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
44.27
76.84
77.16
77.48
112.14
115.70
115.91
116.88
123.40
124.58
124.72
126.46
126.54
126.96
127.58
128.31
128.80
129.55
129.94
130.02
130.44
133.46
141.94
141.97
149.80
151.51
160.56
163.00
Figure 42: 13C-NMR spectra for compound 7ag
65
12 11 10 9 8 7 6 5 4 3 2 1 ppm
0.084
1.549
5.505
7.034
7.038
7.052
7.055
7.086
7.090
7.105
7.214
7.218
7.235
7.238
7.260
7.265
7.279
7.282
7.315
7.317
7.332
7.335
7.338
7.352
7.355
7.373
7.409
7.412
7.429
7.432
7.446
7.449
7.526
7.544
7.592
7.672
7.692
7.772
7.792
7.792
1.0
0
1.0
6
1.0
2
1.2
50.9
5
0.9
1
1.2
0
1.0
9
1.2
52.9
9
1.0
3
1.1
1
1.0
9
Current Data ParametersNAME MK-II-385EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190329Time 15.35INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 322DW 60.800 usecDE 6.00 usecTE 297.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300094 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 43: 1H-NMR spectra for compound 7ah
66
Figure 43a: 1H-NMR spectra expansion for compound 7ah
7.007.057.107.157.207.257.307.357.407.457.507.557.607.657.707.757.80 ppm
7.015
7.019
7.034
7.038
7.052
7.055
7.086
7.090
7.105
7.109
7.214
7.218
7.235
7.238
7.260
7.265
7.279
7.282
7.285
7.315
7.317
7.332
7.335
7.338
7.352
7.355
7.373
7.386
7.409
7.412
7.426
7.429
7.432
7.446
7.449
7.526
7.544
7.592
7.672
7.692
7.772
7.792
7.792
1.0
6
1.0
2
1.2
5
0.9
5
0.9
1
1.2
0
1.0
9
1.2
5
2.9
9
1.0
3
1.1
1
1.0
9
PROTON CDCl3 {D:\CRR} CIF_NMR 1
67
Current Data Parameters
NAME MK-II-385EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190331
Time 10.21INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 292.7 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127603 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
20406080100120140160180 ppm
44.912
76.841
77.159
77.476
112.255
112.350
117.036
122.871
123.530
123.934
124.724
125.575
125.695
125.975
126.012
126.625
126.998
127.582
128.506
128.593
128.690
128.851
128.973
129.057
129.163
129.296
129.529
130.435
133.560
149.639
150.065
151.489
Figure 44: 13C-NMR spectra for compound 7ah
68
12 11 10 9 8 7 6 5 4 3 2 1 ppm
1.570
5.589
7.064
7.067
7.075
7.077
7.251
7.260
7.271
7.299
7.307
7.311
7.313
7.320
7.343
7.346
7.360
7.363
7.366
7.381
7.383
7.438
7.441
7.459
7.462
7.476
7.479
7.527
7.628
7.686
7.697
7.719
7.735
7.793
7.814
0.9
7
1.7
7
1.3
2
1.2
8
0.8
31.0
4
0.9
7
1.0
0
1.9
5
2.1
21.0
0
Current Data ParametersNAME MK-II-398EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190411Time 10.24INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16
DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 406
DW 60.800 usecDE 6.00 usecTE 292.4 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dB
SFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300094 MHz
WDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 45: 1H-NMR spectra for compound 7ai
69
Figure 45a: 1H-NMR spectra expansion for compound 7ai
7.107.157.207.257.307.357.407.457.507.557.607.657.707.757.807.85 ppm
7.064
7.067
7.075
7.077
7.251
7.260
7.271
7.299
7.307
7.311
7.313
7.320
7.343
7.346
7.360
7.363
7.366
7.381
7.383
7.438
7.441
7.459
7.462
7.476
7.479
7.527
7.628
7.686
7.697
7.719
7.735
7.793
7.814
1.7
7
1.3
2
1.2
8
0.8
3
1.0
4
0.9
7
1.0
0
1.9
5
2.1
2
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
70
Current Data Parameters
NAME MK-II-398EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190411
Time 12.24INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 74
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 575DW 20.800 usec
DE 6.00 usec
TE 295.4 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127567 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
44.964
76.844
77.161
77.478
112.794
117.370
121.191
121.952
123.031
123.803
124.663
124.750
124.948
126.893
127.097
127.632
128.367
128.834
129.057
129.365
130.482
132.148
132.479
133.742
148.600
149.479
151.544
Figure 46: 13C-NMR spectra for compound 7ai
71
123456789 ppm2.231
3.703
5.065
6.451
6.457
6.473
6.479
6.572
6.578
6.681
6.682
6.701
6.702
6.811
6.830
6.835
6.843
6.984
7.078
7.096
7.150
7.155
7.167
7.188
2.6
5
3.1
8
1.0
4
1.0
4
1.0
10.8
5
2.8
0
0.7
5
2.5
7
1.9
3
Current Data ParametersNAME MK-II-392EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190403Time 18.53INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 181DW 60.800 usecDE 6.00 usecTE 297.6 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300514 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 47: 1H-NMR spectra for compound 7bc
72
Current Data ParametersNAME MK-II-392
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20190403Time 20.37
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 72
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 45.2DW 20.800 usec
DE 6.00 usecTE 297.8 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.95 usec
PL1 -1.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6127598 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
21.20
43.62
55.50
76.84
77.16
77.48
101.30
110.22
116.80
116.90
121.68
124.30
126.61
128.37
128.48
128.80
129.52
129.66
130.50
137.96
147.17
150.82
151.87
159.43
Figure 48: 13C-NMR spectra for compound 7bc
73
234567891011 ppm
3.840
5.773
6.664
6.670
6.685
6.692
6.886
6.892
7.082
7.100
7.170
7.190
7.208
7.260
7.292
7.314
7.330
7.332
7.350
7.353
7.499
7.506
7.509
7.513
7.516
7.523
7.727
7.732
7.737
7.744
7.752
7.757
7.761
8.653
8.658
8.660
8.672
8.679
8.685
8.703
3.0
3
1.0
0
0.9
9
0.9
81.0
2
2.0
3
1.0
5
1.9
7
2.0
82.1
5
1.0
2
3.1
6
Current Data ParametersNAME MK-II-416EXPNO 1
PROCNO 1
F2 - Acquisition ParametersDate_ 20190509
Time 10.52INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30
TD 65536SOLVENT CDCl3NS 16DS 2
SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 181
DW 60.800 usecDE 6.00 usecTE 291.2 K
D1 1.00000000 secTD0 1
======== CHANNEL f1 ========
NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300093 MHz
WDW EMSSB 0LB 0.30 HzGB 0
PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 49: 1H-NMR spectra for compound 7bf
74
Figure 49a: 1H-NMR spectra expansion for compound 7bf
6.656.706.756.806.856.906.957.007.057.107.157.207.257.307.357.40 ppm
6.664
6.670
6.685
6.692
6.886
6.892
7.063
7.082
7.086
7.097
7.100
7.103
7.170
7.174
7.190
7.204
7.208
7.260
7.292
7.314
7.330
7.332
7.346
7.350
7.353
0.9
9
0.9
8
1.0
2
2.0
3
1.0
5
1.9
7
7.57.67.77.87.98.08.18.28.38.48.58.68.78.8 ppm
7.499
7.506
7.509
7.513
7.516
7.523
7.727
7.732
7.737
7.744
7.752
7.757
7.761
7.973
7.981
7.997
8.636
8.653
8.658
8.660
8.672
8.679
8.685
8.703
2.0
8
2.1
5
1.0
2
3.1
6
75
Current Data Parameters
NAME MK-II-416EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190509
Time 12.14INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 287DW 20.800 usec
DE 6.00 usec
TE 293.0 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127627 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
41.67
55.56
76.84
77.16
77.48
101.51
110.95
112.56
117.34
122.62
122.65
122.98
124.03
124.88
124.89
126.57
126.95
127.16
127.32
127.42
128.13
128.93
129.87
130.58
130.95
145.17
146.60
150.65
159.28
Figure 50: 13C-NMR spectra for compound 7bf
76
12 11 10 9 8 7 6 5 4 3 2 1 ppm
0.082
1.582
3.807
5.196
6.566
6.573
6.588
6.594
6.676
6.683
6.893
6.894
6.915
6.915
6.934
6.956
6.960
6.963
6.972
6.978
6.982
6.996
6.999
7.005
7.010
7.103
7.106
7.123
7.126
7.130
7.135
7.143
7.152
7.159
7.165
7.189
7.194
7.207
7.210
7.260
3.0
0
1.0
7
1.2
7
1.0
0
1.8
22.6
3
1.6
6
3.9
8
1.5
7
Current Data ParametersNAME MK-II-414EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190506Time 11.28INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 228DW 60.800 usecDE 6.00 usecTE 291.0 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300094 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 51: 1H-NMR spectra for compound 7bg
77
Current Data ParametersNAME MK-II-414-A
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20190507Time 15.32
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 187
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 322DW 20.800 usec
DE 6.00 usecTE 293.5 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.95 usec
PL1 -1.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6127597 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
20406080100120140160180 ppm43.11
55.53
76.84
77.16
77.48
101.33
110.44
115.55
115.76
116.39
116.68
123.40
124.47
128.06
128.46
128.91
129.82
129.88
129.96
130.36
142.75
142.78
150.95
151.73
159.54
160.46
162.90
Figure 52: 13C-NMR spectra for compound 7bg
78
11 10 9 8 7 6 5 4 3 2 1 ppm3.826
5.375
6.599
6.606
6.621
6.627
6.720
6.726
6.870
6.891
6.985
6.999
7.005
7.008
7.022
7.025
7.041
7.044
7.155
7.157
7.175
7.178
7.244
7.250
7.260
7.265
7.269
7.281
7.286
7.619
7.715
3.1
5
1.0
3
1.0
31.0
0
1.0
2
2.0
4
0.9
6
1.3
22.0
3
1.0
0
Current Data ParametersNAME MK-II-397-AEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190527Time 14.30INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 406DW 60.800 usecDE 6.00 usecTE 294.6 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300094 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 53: 1H-NMR spectra for compound 7bi
79
Figure 53a: 1H-NMR spectra expansion for compound 7bi
6.56.66.76.86.97.07.17.27.37.47.57.67.77.8 ppm
6.599
6.606
6.621
6.627
6.720
6.726
6.870
6.891
6.985
6.999
7.005
7.008
7.022
7.025
7.041
7.044
7.155
7.157
7.175
7.178
7.244
7.250
7.260
7.265
7.269
7.281
7.286
7.619
7.715
1.0
3
1.0
0
1.0
2
2.0
4
0.9
6
1.3
2
2.0
3
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
80
Current Data Parameters
NAME MK-II-397-AEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190530
Time 11.29INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 294.2 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127564 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\MB} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
43.81
55.58
76.84
77.15
77.47
101.71
110.94
114.62
117.15
120.99
121.99
122.76
123.81
124.70
128.44
128.79
129.60
130.17
131.64
131.97
132.30
149.27
150.99
151.86
160.07
Figure 54: 13C-NMR spectra for compound 7bi
81
23456789101112 ppm
1.579
5.385
7.066
7.068
7.083
7.085
7.088
7.197
7.211
7.214
7.229
7.233
7.244
7.248
7.260
7.264
7.276
7.278
7.282
7.296
7.301
7.315
7.319
7.333
7.337
7.452
7.454
7.456
7.470
7.474
7.485
7.490
7.503
7.504
7.507
1.0
0
2.0
2
3.3
0
4.0
2
2.0
1
1.9
6
Current Data ParametersNAME MK-III-440EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190821Time 15.41INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 144DW 60.800 usecDE 6.00 usecTE 292.3 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300030 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 55: 1H-NMR spectra for compound 9a
82
Figure 56: 13C-NMR spectra for compound 9a
Current Data Parameters
NAME MK-III-440EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190821
Time 17.23INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 36DW 20.800 usec
DE 6.00 usec
TE 292.7 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127682 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
53.12
76.84
77.16
77.47
126.63
126.69
126.97
127.30
127.95
128.30
129.68
133.31
137.44
140.97
83
234567891011 ppm
1.332
1.650
3.783
3.865
5.287
6.789
6.809
6.870
6.891
6.989
7.010
7.051
7.278
7.297
7.315
7.333
7.354
7.438
7.456
7.476
7.494
3.0
63.2
3
0.9
8
2.0
1
1.0
5
2.0
0
1.0
0
3.2
1
1.0
31.0
0
Current Data ParametersNAME MK-ED-43EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190311Time 12.56INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 406DW 60.800 usecDE 6.00 usecTE 295.8 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1299874 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCL3
Figure 57: 1H-NMR spectra for compound 9a
84
Figure 58: 13C-NMR spectra for compound 9b
Current Data ParametersNAME MK-ED-43
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20190311Time 13.01
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 362DW 20.800 usec
DE 6.00 usecTE 295.9 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.15 usec
PL1 0 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.90 dB
PL13 14.90 dBPL2 -3.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6127578 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD
20406080100120140160180 ppm
51.547
55.307
55.618
76.841
77.158
77.476
111.887
112.000
113.109
113.684
126.689
127.233
128.990
129.517
129.977
130.288
130.365
132.946
133.649
134.247
138.193
158.243
158.383
85
11 10 9 8 7 6 5 4 3 2 1 ppm2.302
2.381
5.309
6.962
6.982
7.043
7.063
7.097
7.100
7.116
7.119
7.234
7.238
7.252
7.256
7.259
7.270
7.275
7.288
7.292
7.307
7.310
7.318
7.337
7.425
7.429
7.443
7.447
7.462
7.467
7.481
7.485
3.0
0
3.1
1
1.0
5
2.0
7
2.1
1
1.1
1
2.0
2
1.1
41.1
3
0.9
9
1.0
0
Current Data ParametersNAME MK-III-444EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190828Time 12.08INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 114DW 60.800 usecDE 6.00 usecTE 292.2 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300093 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 59: 1H-NMR spectra for compound 9c
86
Current Data Parameters
NAME MK-III-444EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190828
Time 12.23INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 362DW 20.800 usec
DE 6.00 usec
TE 292.5 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127659 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
21.07
52.37
76.84
77.16
77.47
126.57
126.80
127.26
127.58
127.65
127.80
129.02
129.41
129.58
132.92
133.28
134.66
136.10
136.68
137.87
138.33
Figure 60: 13C-NMR spectra for compound 9c
87
13 12 11 10 9 8 7 6 5 4 3 2 1 ppm
7.091
7.096
7.101
7.108
7.119
7.124
7.204
7.224
7.260
7.333
7.338
7.345
7.351
7.361
7.364
7.368
7.378
7.383
7.544
7.566
7.586
7.602
7.623
7.652
7.654
7.671
7.673
7.759
7.772
7.780
7.786
7.794
7.803
7.809
7.828
7.832
7.856
7.876
9.053
9.075
3.0
7
1.0
0
3.1
1
3.0
9
1.0
43.3
8
1.9
9
0.9
5
1.0
0
Current Data ParametersNAME MK-III-446EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190830Time 12.39INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 406DW 60.800 usecDE 6.00 usecTE 295.6 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300094 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 61: 1H-NMR spectra for compound 9d
88
Figure 61a: 1H-NMR spectra expansion for compound 9d
7.057.107.157.207.257.307.357.407.45 ppm
7.091
7.096
7.101
7.108
7.119
7.124
7.185
7.204
7.224
7.260
7.333
7.338
7.345
7.351
7.361
7.364
7.368
7.378
7.383
3.0
7
1.0
0
3.1
17.557.607.657.707.757.807.857.907.958.008.058.10 ppm
7.544
7.566
7.586
7.602
7.623
7.652
7.654
7.671
7.673
7.759
7.772
7.780
7.786
7.794
7.803
7.809
7.828
7.832
7.850
7.856
7.876
8.020
8.024
8.042
3.0
9
1.0
4
3.3
8
1.9
9
0.9
5
9.1 ppm
9.053
9.075
1.0
0
89
Current Data ParametersNAME MK-III-446
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20190830Time 16.16
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 322DW 20.800 usec
DE 6.00 usecTE 293.9 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.95 usec
PL1 -1.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6127632 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
41.60
76.84
77.16
77.48
122.65
123.22
124.94
125.26
125.41
126.11
126.18
126.69
126.71
126.77
126.83
127.26
127.61
127.85
128.96
129.17
129.74
129.92
130.26
130.55
131.67
132.29
132.75
134.41
135.67
140.55
Figure 62: 13C-NMR spectra for compound 9d
90
12 11 10 9 8 7 6 5 4 3 2 1 ppm
1.456
5.182
6.754
6.776
6.798
6.827
6.832
6.841
6.845
6.849
6.850
6.857
6.862
6.871
6.878
6.899
7.055
7.062
7.077
7.083
7.152
7.156
7.170
7.173
7.174
7.177
7.191
7.195
7.218
7.232
7.240
7.254
7.284
7.288
7.302
7.306
7.326
7.330
7.345
7.348
1.0
5
1.9
8
2.3
50.8
4
1.0
2
2.2
2
1.0
8
1.0
51.0
0
Current Data ParametersNAME MK-III-449EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190910Time 23.05INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 144DW 60.800 usecDE 6.00 usecTE 295.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300567 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 63: 1H-NMR spectra for compound 9e
91
Figure 63a: 1H-NMR spectra expansion for compound 9e
7.147.167.187.207.227.247.267.287.307.327.347.36 ppm
7.133
7.137
7.142
7.152
7.156
7.170
7.173
7.174
7.177
7.191
7.195
7.209
7.213
7.218
7.232
7.240
7.254
7.284
7.288
7.302
7.306
7.326
7.330
7.345
7.348
2.2
2
1.0
8
1.0
5
1.0
0
6.756.806.856.906.957.007.057.10 ppm
6.754
6.776
6.798
6.827
6.832
6.841
6.845
6.849
6.850
6.857
6.862
6.871
6.878
6.892
6.899
7.055
7.062
7.077
7.083
1.9
8
2.3
5
0.8
4
1.0
2
92
Current Data Parameters
NAME MK-III-449EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190911
Time 9.23INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 300
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 36DW 20.800 usec
DE 6.00 usec
TE 294.5 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127599 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
51.69
76.84
77.16
77.48
113.74
113.95
114.09
114.33
115.07
115.28
127.11
127.26
127.34
129.33
129.41
129.62
130.70
130.78
132.47
133.10
133.13
135.17
135.26
136.52
136.55
137.20
160.18
160.48
162.64
162.91
Figure 64: 13C-NMR spectra for compound 9e
93
11 10 9 8 7 6 5 4 3 2 1 ppm
1.592
5.278
6.914
6.935
7.162
7.167
7.178
7.183
7.243
7.249
7.260
7.264
7.269
7.278
7.283
7.296
7.301
7.314
7.318
7.334
7.397
7.400
7.401
7.415
7.419
7.445
7.450
7.455
7.460
7.468
1.0
0
2.0
0
1.9
5
4.1
6
0.9
9
1.9
0
Current Data ParametersNAME MK-II-424-AEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190926Time 15.10INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 161DW 60.800 usecDE 6.00 usecTE 293.1 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300065 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 65: 1H-NMR spectra for compound 9f
94
Current Data Parameters
NAME MK-II-424-AEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190926
Time 15.17INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 456DW 20.800 usec
DE 6.00 usec
TE 293.2 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127614 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
51.94
76.84
77.16
77.47
126.91
127.07
127.15
127.41
127.44
128.50
129.19
129.65
130.54
132.44
132.70
132.87
135.24
135.50
136.69
138.99
Figure 66: 13C-NMR spectra for compound 9f
95
11 10 9 8 7 6 5 4 3 2 1 ppm
4.346
6.952
7.007
7.029
7.050
7.183
7.196
7.205
7.218
7.260
7.274
7.277
7.291
7.294
7.297
7.312
7.314
7.408
7.411
7.425
7.428
7.431
7.445
7.448
7.547
7.567
7.636
7.657
7.741
0.8
4
1.0
14.0
0
4.9
5
1.1
3
1.0
6
1.0
1
1.0
50.9
4
Current Data ParametersNAME MK-II-363-FEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190816Time 9.11INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 144DW 60.800 usecDE 6.00 usecTE 291.2 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300096 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 67: 1H-NMR spectra for compound 2ag
96
Figure 67a: 1H-NMR spectra expansion for compound 2ag
6.97.07.17.27.37.47.57.67.77.8 ppm
6.952
7.007
7.029
7.050
7.183
7.196
7.205
7.218
7.260
7.274
7.277
7.291
7.294
7.297
7.312
7.314
7.408
7.411
7.425
7.428
7.431
7.445
7.448
7.547
7.567
7.636
7.657
7.741
1.0
1
4.0
0
4.9
5
1.1
3
1.0
6
1.0
1
1.0
5
0.9
4
PROTON CDCl3 {D:\CRR} CIF_NMR 1
97
Current Data Parameters
NAME MK-II-363-FEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190816
Time 9.33INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 350
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 36DW 20.800 usec
DE 6.00 usec
TE 291.5 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127592 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.48
83.42
112.31
115.15
115.36
124.08
126.00
127.11
127.74
128.30
129.68
129.76
132.78
134.59
140.64
140.67
153.25
161.24
163.70
Figure 68: 13C-NMR spectra for compound 2ag
98
234567891011 ppm
4.281
6.956
7.165
7.187
7.217
7.260
7.277
7.280
7.294
7.297
7.301
7.312
7.334
7.393
7.413
7.416
7.430
7.433
7.437
7.451
7.454
7.554
7.575
7.652
7.673
0.9
0
0.9
3
3.7
0
0.9
6
0.7
63.8
9
0.8
6
1.1
0
0.9
4
1.0
0
Current Data ParametersNAME MK-ED-75-CLEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190807Time 17.09INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 406DW 60.800 usecDE 6.00 usecTE 294.4 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300095 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 69: 1H-NMR spectra for compound 2ah
99
Current Data Parameters
NAME MK-ED-75-CLEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190808
Time 16.05INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 293.0 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127586 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.47
83.19
112.31
124.17
125.98
127.18
127.80
128.34
128.57
129.30
129.74
132.45
134.19
134.57
143.23
153.01
Figure 70: 13C-NMR spectra for compound 2ah
100
11 10 9 8 7 6 5 4 3 2 1 ppm
4.691
6.927
6.951
7.208
7.260
7.306
7.309
7.323
7.326
7.329
7.344
7.346
7.385
7.405
7.438
7.441
7.456
7.459
7.462
7.476
7.479
7.573
7.594
7.610
7.631
7.652
7.672
0.9
6
0.8
1
0.9
9
0.9
6
1.0
3
3.8
01.0
8
1.0
5
3.8
0
1.0
0
Current Data ParametersNAME MK-ED-34-SEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190807Time 17.14INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 203DW 60.800 usecDE 6.00 usecTE 294.4 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300095 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 71: 1H-NMR spectra for compound 2ai
101
Figure 71a: 1H-NMR spectra expansion for compound 2ai
6.97.07.17.27.37.47.57.67.77.8 ppm
6.927
6.951
7.208
7.260
7.306
7.309
7.323
7.326
7.329
7.344
7.346
7.385
7.405
7.438
7.441
7.456
7.459
7.462
7.476
7.479
7.573
7.594
7.610
7.631
7.652
7.672
0.8
1
0.9
9
0.9
6
1.0
3
3.8
0
1.0
8
1.0
5
3.8
0
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
102
Current Data ParametersNAME MK-ED-34-S
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20190808Time 15.52
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usecTE 292.9 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.95 usec
PL1 -1.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6127593 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.47
82.98
112.29
122.75
124.52
125.36
125.40
125.44
125.96
127.47
127.99
128.16
128.25
128.44
129.85
129.90
130.22
130.55
130.87
132.18
134.48
148.40
152.29
Figure 72: 1H-NMR spectra for compound 2ai
103
9 8 7 6 5 4 3 2 1 ppm
3.757
6.428
6.447
6.635
6.653
6.672
6.782
6.802
7.120
7.125
7.161
7.239
8.081
0.9
8
1.0
61.0
7
1.0
4
5.3
0
6.1
7
1.0
0
Current Data ParametersNAME MK-MM-11EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190215Time 23.26INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 512DW 60.800 usecDE 6.00 usecTE 291.9 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300478 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
Figure 73: 1H-NMR spectra for compound 2ba
104
Current Data Parameters
NAME MK-MM-11EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20181103
Time 15.32INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 362DW 20.800 usec
DE 6.00 usec
TE 295.2 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127611 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.48
84.48
117.65
119.26
127.90
128.02
128.28
129.67
130.12
130.25
144.98
155.98
Figure 74: 13C-NMR spectra for compound 2ba
105
11 10 9 8 7 6 5 4 3 2 1 ppm
3.703
3.801
6.528
6.532
6.548
6.552
6.716
6.719
6.735
6.737
6.753
6.756
6.836
6.841
6.853
6.858
6.866
6.886
6.888
7.105
7.110
7.121
7.127
7.177
7.181
7.197
7.199
7.216
7.220
8.306
0.8
95.9
9
0.9
6
1.0
23.8
2
1.1
3
3.9
3
1.0
4
1.0
0
Current Data ParametersNAME MK-MM-15EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190701Time 16.22INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 144DW 60.800 usecDE 6.00 usecTE 296.2 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300092 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 75: 1H-NMR spectra for compound 2bb
106
Current Data Parameters
NAME MK-MM-15EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190701
Time 16.30INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 322DW 20.800 usec
DE 6.00 usec
TE 296.2 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127599 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
55.39
76.84
77.16
77.48
84.12
113.53
117.63
119.09
129.15
129.56
130.02
130.52
137.46
156.16
159.19
Figure 76: 13C-NMR spectra for compound 2bb
107
Figure 77: 1H-NMR spectra for compound 2bc
9 8 7 6 5 4 3 2 1 ppm2.236
3.740
6.417
6.419
6.436
6.588
6.607
6.626
6.718
6.737
6.951
6.971
6.998
7.018
7.038
7.041
7.059
7.076
7.079
8.215
6.2
7
1.0
0
1.0
2
1.0
8
1.0
0
4.1
5
4.4
11.2
7
1.0
0
Current Data ParametersNAME MK-MM-16EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190212Time 10.58INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 57DW 60.800 usecDE 6.00 usecTE 292.8 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300724 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCL3
108
Current Data ParametersNAME MK-MM-16
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20190215Time 16.00
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT DMSONS 256
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 362DW 20.800 usec
DE 6.00 usecTE 296.3 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.15 usec
PL1 0 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.90 dB
PL13 14.90 dBPL2 -3.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6126938 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCL3M.KARTHICK
180 160 140 120 100 80 60 40 20 ppm
21.12
21.18
76.84
77.16
77.48
84.26
117.54
119.10
127.56
127.79
128.02
128.10
128.26
128.64
128.90
129.11
129.22
129.47
130.02
130.49
137.60
142.23
156.01
Figure 78: 13C-NMR spectra for compound 2bc
109
Figure 79: 1H-NMR spectra for compound 2bd
13 12 11 10 9 8 7 6 5 4 3 2 1 ppm
4.713
6.642
6.643
6.645
6.965
6.983
7.026
7.029
7.047
7.050
7.164
7.184
7.203
7.243
7.247
7.260
7.263
7.338
7.359
7.377
7.414
7.419
7.436
7.440
7.482
7.758
7.779
7.845
7.866
7.879
7.900
7.919
7.920
7.940
7.942
7.962
8.436
8.697
0.9
8
0.9
4
0.9
8
1.9
2
0.9
7
1.0
3
1.0
6
0.8
1
1.0
5
2.2
9
0.9
0
1.0
0
2.1
1
2.0
0
0.9
5
0.8
5
Current Data ParametersNAME MK-III-433-BEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190710Time 11.18INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 256DW 60.800 usecDE 6.00 usecTE 294.6 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300096 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
110
Figure 79a: 1H-NMR spectra expansion for compound 2bd
6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.08.18.28.38.48.58.68.78.8 ppm
6.478
6.494
6.498
6.627
6.642
6.643
6.645
6.965
6.983
7.026
7.029
7.047
7.050
7.164
7.184
7.203
7.243
7.247
7.260
7.263
7.338
7.359
7.377
7.410
7.414
7.419
7.422
7.431
7.436
7.440
7.442
7.462
7.465
7.482
7.485
7.758
7.779
7.845
7.866
7.879
7.900
7.919
7.920
7.940
7.942
7.962
8.436
8.457
8.697
0.9
4
0.9
8
1.9
2
0.9
7
1.0
3
1.0
6
0.8
1
1.0
5
2.2
9
0.9
0
1.0
0
2.1
1
2.0
0
0.9
5
0.8
5
PROTON CDCl3 {D:\CRR} CIF_NMR 1
111
Current Data Parameters
NAME MK-III-433-BEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190710
Time 16.46INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 158
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 456DW 20.800 usec
DE 6.00 usec
TE 296.3 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127601 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.47
88.43
118.06
119.73
124.31
125.28
125.42
125.65
126.08
126.22
127.16
127.69
127.72
129.17
129.28
129.89
130.04
130.27
131.03
131.14
135.31
135.37
139.16
140.08
156.23
Figure 80: 13C-NMR spectra for compound 2bd
112
23456789 ppm
1.651
2.288
3.954
6.343
6.363
6.562
6.563
6.566
6.583
6.585
6.587
6.692
6.695
7.125
7.141
7.146
7.260
7.290
7.295
7.306
7.311
7.508
3.0
6
1.1
1
1.0
4
1.1
1
1.0
3
3.9
4
3.8
51.0
0
Current Data ParametersNAME MK-MM-44EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190327Time 14.52INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 228DW 60.800 usecDE 6.00 usecTE 296.4 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300094 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 81: 1H-NMR spectra for compound 2ch
113
Current Data ParametersNAME MK-MM-44
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20190331Time 11.00
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 87
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usecTE 292.6 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.95 usec
PL1 -1.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6127688 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
21.04
76.84
77.16
77.48
83.07
118.00
120.63
127.29
128.35
129.27
129.46
129.66
133.87
140.14
143.47
154.77
Figure 82: 13C-NMR spectra for compound 2ch
114
234567891011 ppm
3.453
3.619
7.282
7.301
7.317
7.444
7.463
7.481
7.647
7.668
7.746
7.767
8.477
10.359
3.0
4
3.0
3
2.1
2
1.0
9
1.1
01.0
7
0.9
8
1.0
0
Current Data ParametersNAME MK-II-369-FEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190501Time 9.45INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 101DW 60.800 usecDE 6.00 usecTE 290.9 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300137 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 83: 1H-NMR spectra for compound 4
115
Current Data Parameters
NAME MK-II-369-FEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190501
Time 10.06INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 350
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 256DW 20.800 usec
DE 6.00 usec
TE 291.1 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127655 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm34.09
61.45
76.84
77.16
77.48
111.85
117.04
123.80
126.19
127.04
128.60
129.16
131.27
136.47
155.67
169.28
Figure 84: 13C-NMR spectra for compound 4
116
2345678910111213 ppm
7.260
7.296
7.299
7.316
7.319
7.334
7.336
7.388
7.514
7.516
7.531
7.535
7.538
7.543
7.547
7.552
7.555
7.557
7.561
7.581
7.642
7.645
7.648
7.659
7.664
7.669
7.682
7.702
7.716
7.718
7.736
7.764
7.768
7.785
7.788
8.173
11.184
1.2
2
1.0
4
3.2
11.1
1
2.0
7
1.9
2
1.0
0
0.9
2
Current Data ParametersNAME MK-II-370-ZEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190825Time 10.44INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 114DW 60.800 usecDE 6.00 usecTE 290.9 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300092 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 85: 1H-NMR spectra for compound 5
117
Current Data Parameters
NAME MK-II-370-ZEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190825
Time 11.06INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 350
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 362DW 20.800 usec
DE 6.00 usec
TE 290.9 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127651 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
200 180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.47
112.43
121.06
124.16
126.35
126.77
128.57
129.64
129.67
129.89
132.43
136.80
137.97
138.01
157.35
201.83
Figure 86: 1H-NMR spectra for compound 5
118
11 10 9 8 7 6 5 4 3 2 1 ppm
3.812
4.058
6.850
6.872
7.018
7.131
7.153
7.228
7.235
7.244
7.253
7.260
7.264
7.282
7.284
7.340
7.348
7.356
7.388
7.390
7.408
7.411
7.426
7.428
7.539
7.559
7.649
7.670
8.189
3.1
4
0.9
9
2.0
8
1.0
8
2.0
3
4.6
9
3.0
71.1
7
1.1
7
1.1
3
1.0
0
Current Data ParametersNAME MK-II-371-CEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190711Time 14.19INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 144DW 60.800 usecDE 6.00 usecTE 293.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300094 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 87: 1H-NMR spectra for compound 6aa
119
Figure 87a: 1H-NMR spectra expansion for compound 6aa
6.97.07.17.27.37.47.57.67.77.87.98.08.18.2 ppm
6.850
6.872
7.018
7.131
7.153
7.228
7.235
7.244
7.253
7.260
7.264
7.282
7.284
7.340
7.348
7.356
7.388
7.390
7.408
7.411
7.426
7.428
7.539
7.559
7.649
7.670
8.189
2.0
8
1.0
8
2.0
3
4.6
9
3.0
7
1.1
7
1.1
7
1.1
3
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
120
Current Data Parameters
NAME MK-II-371-CEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190711
Time 14.24INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 406DW 20.800 usec
DE 6.00 usec
TE 293.6 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127614 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
55.40
76.84
77.16
77.47
84.24
112.18
113.61
123.65
126.01
126.75
127.62
127.84
128.06
128.26
128.31
129.31
129.79
133.05
134.66
137.03
144.90
154.00
159.28
Figure 88: 13C-NMR spectra for compound 6aa
121
11 10 9 8 7 6 5 4 3 2 1 ppm
3.728
6.331
6.520
6.524
6.539
6.543
6.871
6.880
7.029
7.049
7.242
7.260
7.306
7.328
7.364
7.412
7.501
7.521
7.710
7.731
9.133
3.1
4
0.8
9
0.9
6
1.9
6
1.0
0
1.2
8
2.3
70.9
7
4.1
6
1.2
1
1.1
1
1.0
0
1.0
0
Current Data ParametersNAME MK-II-420-AEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190520Time 11.31INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 144DW 60.800 usecDE 6.00 usecTE 293.3 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300093 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 89: 1H-NMR spectra for compound 6ab
122
Figure 89a: 1H-NMR spectra expansion for compound 6ab
6.36.46.56.66.76.86.97.07.17.27.37.47.57.67.77.8 ppm
6.331
6.520
6.524
6.539
6.543
6.871
6.880
7.029
7.049
7.242
7.260
7.306
7.328
7.364
7.412
7.501
7.521
7.710
7.731
0.8
9
0.9
6
1.9
6
1.0
0
1.2
8
2.3
7
0.9
7
4.1
6
1.2
1
1.1
1
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
123
Current Data Parameters
NAME MK-II-420-AEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190520
Time 16.20INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 222
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 293.2 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127669 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
56.02
76.84
77.16
77.48
84.64
112.09
112.25
121.21
123.29
126.02
126.58
127.49
127.98
128.21
128.85
129.96
130.03
132.03
132.35
134.91
144.04
154.85
157.18
Figure 90: 13C-NMR spectra for compound 6ab
124
11 10 9 8 7 6 5 4 3 2 1 ppm
2.29
3.78
6.93
7.02
7.04
7.07
7.09
7.15
7.16
7.18
7.19
7.26
7.27
7.27
7.30
7.30
7.32
7.34
7.34
7.45
7.47
7.58
7.60
7.99
3.0
0
1.0
5
0.9
8
2.1
3
2.1
8
4.6
1
3.1
01.2
1
1.1
1
1.0
4
0.9
5
Current Data Parameters
NAME MK-II-395
EXPNO 1PROCNO 1
F2 - Acquisition Parameters
Date_ 20190405Time 22.40
INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgigTD 32768
SOLVENT CDCl3
NS 16DS 2
SWH 8333.333 Hz
FIDRES 0.254313 Hz
AQ 1.9660800 secRG 203
DW 60.000 usec
DE 6.00 usec
TE 294.4 KD1 1.00000000 sec
d11 0.03000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 14.35 usecPL1 -1.00 dB
SFO1 400.1325018 MHz
======== CHANNEL f2 ========CPDPRG[2 garp
NUC2 31P
PCPD2 100.00 usec
PL12 120.00 dBPL2 0 dB
SFO2 161.9760648 MHz
F2 - Processing parameters
SI 32768
SF 400.1300442 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0
PC 1.40
PROP31DEC CDCl3 {D:\CRR} CIF_NMR 1
Figure 91: 1H-NMR spectra for compound 6ac
125
Figure 91a: 1H-NMR spectra expansion for compound 6ac
6.97.07.17.27.37.47.57.67.77.87.98.08.1 ppm
6.925
7.020
7.041
7.065
7.086
7.153
7.165
7.177
7.187
7.258
7.266
7.274
7.299
7.301
7.319
7.337
7.338
7.448
7.468
7.579
7.599
7.995
0.9
8
2.1
3
2.1
8
4.6
1
3.1
0
1.2
1
1.1
1
1.0
4
0.9
5
PROP31DEC CDCl3 {D:\CRR} CIF_NMR 1
126
Current Data Parameters
NAME MK-II-395EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190406
Time 0.39INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 77
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 294.4 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127619 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
21.22
76.84
77.16
77.48
84.34
112.17
123.63
126.02
126.74
127.64
127.86
127.92
128.05
128.29
129.05
129.80
133.02
134.66
137.89
141.90
144.87
154.00
Figure 92: 13C-NMR spectra for compound 6ac
127
10 9 8 7 6 5 4 3 2 1 ppm
2.970
6.665
6.688
7.044
7.067
7.070
7.254
7.260
7.266
7.276
7.285
7.328
7.334
7.342
7.346
7.375
7.378
7.393
7.396
7.399
7.546
7.567
7.666
7.687
6.0
6
2.1
2
2.9
9
4.5
4
3.0
31.2
6
1.1
3
1.0
0
Current Data ParametersNAME MK-II-422EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190527Time 14.35INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 228DW 60.800 usecDE 6.00 usecTE 294.6 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300094 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 93: 1H-NMR spectra for compound 6ad
128
Figure 93a: 1H-NMR spectra expansion for compound 6ad
6.76.86.97.07.17.27.37.47.57.67.77.8 ppm
6.665
6.688
7.044
7.067
7.070
7.254
7.260
7.266
7.276
7.285
7.328
7.334
7.342
7.346
7.375
7.378
7.393
7.396
7.399
7.546
7.567
7.666
7.687
2.1
2
2.9
9
4.5
4
3.0
3
1.2
6
1.1
3
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
129
Current Data Parameters
NAME MK-II-422EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190530
Time 13.40INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 512
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 293.5 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127590 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
40.54
76.84
77.16
77.47
84.57
111.93
112.09
123.45
126.01
126.59
127.59
127.84
128.19
128.27
128.63
128.98
129.72
129.80
132.57
133.27
134.72
144.98
150.18
154.45
Figure 94: 13C-NMR spectra for compound 6ad
130
11 10 9 8 7 6 5 4 3 2 1 ppm
1.604
4.455
6.850
6.852
6.869
6.870
6.983
7.182
7.184
7.202
7.220
7.222
7.260
7.281
7.301
7.320
7.367
7.373
7.397
7.415
7.418
7.435
7.453
7.686
7.707
7.871
7.892
7.903
7.924
8.138
8.159
8.285
0.97
0.98
1.05
1.23
1.92
1.77
3.66
3.49
1.09
2.09
0.98
1.00
Current Data ParametersNAME MK-II-402EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190424Time 11.01INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 287DW 60.800 usecDE 6.00 usecTE 297.4 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300093 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 95: 1H-NMR spectra for compound 6ae
131
Figure 95a: 1H-NMR spectra expansion for compound 6ae
6.97.07.17.27.37.47.57.67.77.87.98.08.18.28.3 ppm
6.850
6.852
6.869
6.870
6.983
7.182
7.184
7.202
7.220
7.222
7.260
7.281
7.301
7.320
7.367
7.373
7.397
7.415
7.418
7.435
7.453
7.686
7.707
7.871
7.892
7.903
7.924
8.138
8.159
8.285
0.9
8
1.0
5
1.2
3
1.9
2
1.7
7
3.6
6
3.4
9
1.0
9
2.0
9
0.9
8
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
132
Current Data Parameters
NAME MK-II-402EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190424
Time 11.47INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 512
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 45.2DW 20.800 usec
DE 6.00 usec
TE 296.8 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127572 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.48
85.90
112.50
123.59
124.62
125.66
126.03
126.24
126.76
127.60
127.76
127.90
128.03
128.33
128.45
128.48
129.41
129.71
130.19
131.07
132.32
134.75
135.25
140.02
144.53
153.90
Figure 96: 13C-NMR spectra for compound 6ae
133
13 12 11 10 9 8 7 6 5 4 3 2 1 ppm
2.496
2.500
3.402
6.912
7.009
7.083
7.100
7.119
7.236
7.244
7.266
7.284
7.300
7.383
7.402
7.425
7.444
7.462
7.482
7.499
7.502
7.567
7.588
7.592
7.599
7.620
7.727
8.450
8.471
8.609
8.630
8.655
8.676
10.213
1.1
0
1.1
32.1
8
6.9
8
3.9
6
2.3
3
1.0
81.1
2
1.0
4
1.0
0
Current Data ParametersNAME MK-UN-04-AEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190702Time 12.50INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT DMSO
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 128DW 60.800 usecDE 6.00 usecTE 294.2 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300044 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON DMSO {D:\CRR} CIF_NMR 1
Figure 97: 1H-NMR spectra for compound 6af
134
Figure 97a: 1H-NMR spectra expansion for compound 6af
6.97.07.17.27.37.47.57.67.77.87.98.08.18.28.38.48.58.68.78.8 ppm
6.912
7.009
7.083
7.100
7.119
7.236
7.244
7.266
7.284
7.300
7.383
7.402
7.425
7.444
7.462
7.482
7.499
7.502
7.567
7.588
7.592
7.599
7.620
7.727
8.450
8.471
8.609
8.630
8.655
8.676
1.1
0
1.1
3
2.1
8
6.9
8
3.9
6
2.3
3
1.0
8
1.1
2
1.0
4
PROTON DMSO {D:\CRR} CIF_NMR 1
11 ppm
10.213
1.0
0
135
Current Data ParametersNAME MK-UN-04-A
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20190703Time 11.19
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT DMSONS 512
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 322DW 20.800 usec
DE 6.00 usecTE 292.9 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.95 usec
PL1 -1.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6128072 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD DMSO {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
38.87
39.08
39.29
39.50
39.71
39.92
40.13
77.66
77.98
78.31
83.93
110.89
122.00
122.42
123.01
125.22
125.32
125.69
126.12
126.46
127.08
127.61
127.71
127.80
128.41
128.67
128.96
130.05
130.16
131.23
133.85
139.07
145.39
153.59
Figure 98: 13C-NMR spectra for compound 6af
136
23456789101112 ppm
4.42
6.99
7.00
7.02
7.04
7.20
7.22
7.22
7.23
7.24
7.26
7.26
7.27
7.28
7.28
7.29
7.30
7.30
7.35
7.35
7.36
7.37
7.40
7.40
7.42
7.42
7.42
7.44
7.44
7.54
7.56
7.63
7.65
8.04
0.9
1
1.0
6
2.2
31.7
2
3.5
4
1.1
5
3.4
3
1.2
21.1
4
1.1
4
1.0
0
Current Data ParametersNAME MK-II-378-OEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190815Time 13.18INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 128DW 60.800 usecDE 6.00 usecTE 291.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300095 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 99: 1H-NMR spectra for compound 6ag
137
Figure 99a: 1H-NMR spectra expansion for compound 6ag
7.07.17.27.37.47.57.67.77.87.98.08.1 ppm
6.986
6.997
7.018
7.040
7.203
7.216
7.225
7.233
7.238
7.260
7.264
7.267
7.282
7.285
7.287
7.302
7.305
7.349
7.352
7.360
7.366
7.401
7.404
7.418
7.421
7.424
7.439
7.441
7.543
7.564
7.632
7.653
8.037
1.0
6
2.2
3
1.7
2
3.5
4
1.1
5
3.4
3
1.2
2
1.1
4
1.1
4
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
138
Figure 100: 13C-NMR spectra for compound 6ag
180 160 140 120 100 80 60 40 20 ppm
76.84
77.15
77.47
83.86
112.20
114.99
115.20
123.88
125.99
126.93
127.68
127.81
128.21
128.27
128.40
129.79
129.87
132.90
134.58
140.65
140.68
144.76
153.51
161.16
163.61
Current Data Parameters
NAME MK-II-378-O
EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190815
Time 13.39
INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 350
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 36
DW 20.800 usec
DE 6.00 usec
TE 291.7 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usec
PL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dB
PL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127630 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
139
234567891011 ppm
4.392
6.984
7.208
7.217
7.221
7.227
7.233
7.260
7.272
7.275
7.290
7.293
7.296
7.310
7.313
7.369
7.372
7.374
7.380
7.386
7.396
7.416
7.429
7.433
7.436
7.450
7.453
7.549
7.549
7.569
7.570
7.587
7.608
7.626
7.649
0.9
3
0.8
6
2.7
61.0
5
2.7
2
3.2
3
0.9
8
1.9
5
0.8
61.0
0
Current Data ParametersNAME MK-II-381EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190401Time 10.58INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 181DW 60.800 usecDE 6.00 usecTE 292.4 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300095 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 101: 1H-NMR spectra for compound 6ah
140
Figure 101a: 1H-NMR spectra expansion for compound 6ah
7.007.057.107.157.207.257.307.357.407.457.507.557.607.657.70 ppm
6.984
7.208
7.217
7.221
7.227
7.233
7.260
7.272
7.275
7.290
7.293
7.296
7.310
7.313
7.369
7.372
7.374
7.380
7.386
7.396
7.416
7.429
7.433
7.436
7.450
7.453
7.549
7.549
7.569
7.570
7.587
7.608
7.626
7.649
7.650
7.670
0.8
6
2.7
6
1.0
5
2.7
2
3.2
3
0.9
8
1.9
5
0.8
6
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
141
Current Data Parameters
NAME MK-II-381EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190402
Time 15.39INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 125
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 45.2DW 20.800 usec
DE 6.00 usec
TE 294.4 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127585 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.48
83.75
112.33
124.08
125.22
125.26
125.96
126.01
127.12
127.80
127.87
128.33
128.43
128.56
129.87
129.95
132.56
134.61
144.44
148.78
153.24
Figure 102: 13C-NMR spectra for compound 6ah
142
12 11 10 9 8 7 6 5 4 3 2 1 ppm4.876
6.961
7.173
7.200
7.210
7.220
7.225
7.260
7.308
7.310
7.325
7.328
7.345
7.348
7.391
7.393
7.401
7.407
7.441
7.443
7.461
7.464
7.479
7.481
7.571
7.591
7.647
7.667
7.818
7.888
1.0
4
1.0
2
0.9
93.0
8
1.1
1
3.0
5
1.1
3
1.0
41.0
7
2.0
1
1.0
0
Current Data ParametersNAME MK-II-384-SEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20191104Time 10.17INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16
DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 144
DW 60.800 usecDE 6.00 usecTE 290.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dB
SFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300094 MHz
WDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 103: 1H-NMR spectra for compound 6ai
143
Figure 103a: 1H-NMR spectra expansion for compound 6ai
7.07.17.27.37.47.57.67.77.87.9 ppm
6.961
7.173
7.200
7.210
7.220
7.225
7.260
7.308
7.310
7.325
7.328
7.345
7.348
7.391
7.393
7.401
7.407
7.441
7.443
7.461
7.464
7.479
7.481
7.571
7.591
7.647
7.667
7.818
7.888
1.0
2
0.9
9
3.0
8
1.1
1
3.0
5
1.1
3
1.0
4
1.0
7
2.0
1
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
144
Figure 104: 13C-NMR spectra for compound 6ai
Current Data Parameters
NAME MK-II-384-SEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20191104
Time 11.20INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 1024
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 362DW 20.800 usec
DE 6.00 usec
TE 291.0 KD1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1HPCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127592 MHz
WDW EM
SSB 0LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.47
83.01
112.34
121.96
122.04
124.42
124.75
125.98
127.39
127.70
127.98
128.03
128.47
128.66
128.75
129.97
131.32
131.65
132.18
134.53
143.92
148.12
152.29
145
Figure 105: 1H-NMR spectra for compound 6bc
9 8 7 6 5 4 3 2 1 ppm
1.646
2.362
3.592
3.760
6.279
6.285
6.300
6.307
6.401
6.422
6.470
6.477
7.065
7.081
7.086
7.134
7.155
7.199
7.204
7.216
7.223
7.260
7.314
7.322
7.326
7.340
8.326
3.0
9
1.0
1
3.0
1
1.0
0
0.9
8
0.9
3
2.0
4
1.9
2
1.9
9
2.9
6
1.0
0
Current Data ParametersNAME MK-MM-45EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190331Time 10.15INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 181DW 60.800 usecDE 6.00 usecTE 292.6 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300094 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
146
Current Data ParametersNAME MK-MM-45
EXPNO 2PROCNO 1
F2 - Acquisition Parameters
Date_ 20190331Time 11.20
INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 100
DS 4SWH 24038.461 Hz
FIDRES 0.366798 HzAQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usecTE 292.8 K
D1 2.00000000 secd11 0.03000000 sec
DELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========
NUC1 13CP1 9.95 usec
PL1 -1.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usecPL12 14.95 dB
PL13 120.00 dBPL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parametersSI 32768
SF 100.6127633 MHzWDW EM
SSB 0LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
21.17
55.34
76.84
77.16
77.48
84.17
102.75
105.13
122.82
127.78
127.83
127.89
128.21
128.96
130.75
137.73
142.34
145.29
157.30
160.71
Figure 106: 13C-NMR spectra for compound 6bc
147
2345678910111213 ppm
3.775
4.204
6.225
6.231
6.247
6.253
6.456
6.477
6.553
6.560
7.107
7.380
7.410
7.414
7.428
7.431
7.434
7.449
7.452
7.532
7.550
7.552
7.582
7.585
7.603
7.606
7.620
7.640
7.643
7.646
7.660
7.664
7.667
8.199
8.220
8.438
8.649
8.670
8.753
8.773
3.0
2
0.9
9
0.9
9
0.9
9
0.9
8
0.9
94.8
4
1.3
0
1.0
6
3.3
0
1.0
1
1.0
01.0
1
1.0
0
Current Data ParametersNAME MK-II-415EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190507Time 15.15INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 203DW 60.800 usecDE 6.00 usecTE 293.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300094 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 107: 1H-NMR spectra for compound 6bf
148
Figure 107a: 1H-NMR spectra expansion for compound 6bf
6.36.46.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.08.18.28.38.48.58.68.78.88.9 ppm
6.225
6.231
6.247
6.253
6.456
6.477
6.553
6.560
7.107
7.380
7.410
7.414
7.428
7.431
7.434
7.449
7.452
7.513
7.515
7.532
7.550
7.552
7.582
7.585
7.603
7.606
7.620
7.640
7.643
7.646
7.660
7.664
7.667
7.681
7.684
8.199
8.220
8.438
8.649
8.670
8.753
8.773
0.9
9
0.9
9
0.9
8
0.9
9
4.8
4
1.3
0
1.0
6
3.3
0
1.0
1
1.0
0
1.0
1
1.0
0
PROTON CDCl3 {D:\CRR} CIF_NMR 1
149
Current Data Parameters
NAME MK-II-415EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190507
Time 16.31INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 293.3 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127598 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 0 ppm
55.36
76.84
77.16
77.47
85.68
103.04
105.47
122.15
122.40
123.63
126.34
126.46
126.99
127.75
127.81
127.96
128.40
129.70
129.73
129.96
130.52
130.73
130.76
132.09
137.99
144.97
156.96
160.84
Figure 108: 13C-NMR spectra for compound 6bf
150
123456789 ppm
3.752
3.819
6.285
6.291
6.306
6.313
6.371
6.393
6.454
6.460
6.985
7.007
7.029
7.162
7.165
7.167
7.178
7.181
7.187
7.200
7.329
7.334
7.342
7.346
8.218
3.0
21.0
0
0.9
8
0.9
50.9
7
1.8
7
3.8
22.7
2
0.9
2
Current Data ParametersNAME MK-II-411EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190501Time 9.40INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 144DW 60.800 usecDE 6.00 usecTE 290.8 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300093 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 109: 1H-NMR spectra for compound 6bg
151
Current Data Parameters
NAME MK-II-411EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190504
Time 22.51INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 350
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3DW 20.800 usec
DE 6.00 usec
TE 291.1 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127619 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
55.37
76.85
77.16
77.48
83.75
102.88
105.22
114.91
115.12
122.77
127.73
128.09
128.35
129.72
129.80
130.67
141.04
141.07
145.16
157.03
160.79
161.08
163.54
Figure 110: 13C-NMR spectra for compound 6bg
152
9 8 7 6 5 4 3 2 1 ppm
3.771
4.127
6.350
6.355
6.364
6.452
6.457
7.116
7.120
7.122
7.127
7.131
7.140
7.260
7.367
7.371
7.375
7.384
7.390
7.568
7.755
7.848
3.0
8
0.9
5
0.8
4
0.8
1
0.9
7
2.0
5
3.0
60.9
5
2.0
2
1.0
0
Current Data ParametersNAME MK-MM-46EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190405Time 22.36INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 203DW 60.800 usecDE 6.00 usecTE 294.4 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300095 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 111: 1H-NMR spectra for compound 6bi
153
Current Data Parameters
NAME MK-MM-46EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190406
Time 0.26INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 134
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 45.2DW 20.800 usec
DE 6.00 usec
TE 294.5 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127565 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
55.45
76.84
77.16
77.48
83.28
103.33
105.74
121.92
122.05
122.09
124.76
127.64
128.02
128.71
128.80
130.64
130.98
131.31
131.64
131.98
144.22
148.16
156.40
161.15
Figure 112: 13C-NMR spectra for compound 6bi
154
Figure 113: 1H-NMR spectra for compound 8a
12 11 10 9 8 7 6 5 4 3 2 1 ppm
3.460
5.153
6.648
6.651
6.667
6.671
7.041
7.045
7.060
7.064
7.080
7.083
7.161
7.165
7.180
7.184
7.199
7.203
7.260
7.281
7.285
7.301
7.306
7.316
7.327
7.332
7.339
7.343
7.358
7.363
7.369
7.373
7.379
7.396
7.399
7.415
7.419
0.9
3
0.9
3
0.9
6
1.0
1
0.9
93.8
2
3.9
0
2.0
9
1.0
0
Current Data ParametersNAME MK-III-434EXPNO 3
PROCNO 1
F2 - Acquisition ParametersDate_ 20190817
Time 14.56INSTRUM spectPROBHD 5 mm BBO BB-1H
PULPROG zg30TD 65536SOLVENT CDCl3NS 16
DS 2SWH 8223.685 HzFIDRES 0.125483 Hz
AQ 3.9845889 secRG 144DW 60.800 usecDE 6.00 usec
TE 290.8 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usec
PL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300095 MHzWDW EM
SSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
155
Current Data Parameters
NAME MK-III-434EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190714
Time 11.51INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 350
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 36DW 20.800 usec
DE 6.00 usec
TE 291.5 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127587 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.36
77.47
82.91
126.38
127.56
127.81
128.04
128.19
128.26
128.35
128.46
129.13
130.83
134.78
145.78
146.26
Figure 114: 13C-NMR spectra for compound 8a
156
Figure 115: 1H-NMR spectra for compound 8b
9 8 7 6 5 4 3 2 1 ppm
3.809
4.141
6.633
6.636
6.653
6.655
6.828
6.850
6.998
7.000
7.018
7.037
7.108
7.130
7.138
7.158
7.160
7.261
7.435
7.454
6.1
4
0.9
3
1.0
1
4.5
7
1.0
8
3.8
7
1.3
1
1.0
0
Current Data ParametersNAME MK-MM-26EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190123Time 15.09INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 32DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 287DW 60.800 usecDE 6.00 usecTE 294.2 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300045 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {
157
Figure 116: 13C-NMR spectra for compound 8b
180 160 140 120 100 80 60 40 20 ppm
55.37
76.84
77.16
77.47
82.41
113.42
126.17
128.54
129.28
129.64
129.95
136.76
138.47
145.86
158.89
Current Data Parameters
NAME MK-MM-26
EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190123
Time 15.11
INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 256
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 45.2
DW 20.800 usec
DE 6.00 usec
TE 294.2 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usec
PL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dB
PL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127564 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} nmr 1
158
Figure 117: 1H-NMR spectra for compound 8c
10 9 8 7 6 5 4 3 2 1 ppm2.357
4.102
6.626
6.629
6.646
6.649
6.993
6.996
7.012
7.015
7.031
7.034
7.081
7.087
7.096
7.102
7.111
7.127
7.131
7.145
7.149
7.260
7.427
7.430
7.447
7.450
5.9
8
1.0
0
1.0
1
1.0
2
4.2
8
4.9
3
1.0
0
Current Data ParametersNAME MK-MM-27EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190614Time 14.50INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 322DW 60.800 usecDE 6.00 usecTE 295.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300095 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
159
Figure 118: 13C-NMR spectra for compound 8c
180 160 140 120 100 80 60 40 20 ppm
21.23
76.84
77.16
77.48
82.71
126.06
127.93
128.47
128.83
129.62
130.01
136.83
137.09
143.24
145.66
Current Data Parameters
NAME MK-MM-27
EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190616
Time 15.10
INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 256
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3
DW 20.800 usec
DE 6.00 usec
TE 294.2 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usec
PL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dB
PL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127620 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
160
Figure 119: 1H-NMR spectra for compound 8d
15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 ppm
4.850
6.623
6.642
6.669
6.687
6.847
6.866
6.885
6.901
6.920
6.985
7.005
7.024
7.145
7.156
7.172
7.202
7.222
7.236
7.314
7.332
7.345
7.363
7.597
7.618
7.687
7.708
7.723
7.743
7.775
7.795
7.816
8.098
8.111
8.119
8.132
8.250
8.271
0.9
3
0.9
5
1.9
1
2.1
1
1.0
8
3.2
4
2.1
1
2.1
6
2.9
8
1.0
0
0.8
8
Current Data ParametersNAME MK-III-445-AEXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20190911Time 15.48INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zgigTD 32768SOLVENT CDCl3NS 16DS 2SWH 8333.333 HzFIDRES 0.254313 HzAQ 1.9660800 secRG 114DW 60.000 usecDE 6.00 usecTE 294.6 KD1 1.00000000 secd11 0.03000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1325018 MHz
======== CHANNEL f2 ========CPDPRG[2 garpNUC2 31PPCPD2 100.00 usecPL12 120.00 dBPL2 0 dBSFO2 161.9760648 MHz
F2 - Processing parametersSI 32768SF 400.1300548 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
PROP31DEC CDCl3 {D:\CRR} CIF_NMR 1
161
Figure 119a: 1H-NMR spectra expansion for compound 8d
6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.08.18.28.38.4 ppm
6.541
6.623
6.642
6.669
6.687
6.847
6.866
6.885
6.901
6.920
6.985
7.005
7.024
7.145
7.156
7.172
7.202
7.222
7.236
7.314
7.332
7.345
7.363
7.597
7.618
7.687
7.708
7.723
7.743
7.775
7.795
7.816
8.098
8.111
8.119
8.132
8.250
8.271
0.9
5
1.9
1
2.1
1
1.0
8
3.2
4
2.1
1
2.1
6
2.9
8
1.0
0
0.8
8
PROP31DEC CDCl3 {D:\CRR} CIF_NMR 1
162
Figure 120: 13C-NMR spectra for compound 8d
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.48
87.41
124.30
124.58
125.43
125.61
126.91
127.25
128.62
128.79
129.06
129.13
129.44
129.79
130.71
131.61
131.62
131.92
135.24
135.41
135.48
136.69
136.79
140.26
140.41
141.35
141.53
145.96
146.47
Current Data Parameters
NAME MK-III-445-A
EXPNO 1
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190911
Time 22.37
INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 602
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 322
DW 20.800 usec
DE 6.00 usec
TE 298.8 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usec
PL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dB
PL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127587 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
163
10 9 8 7 6 5 4 3 2 1 ppm
3.313
5.057
6.477
6.480
6.497
6.500
6.820
6.825
6.842
6.858
6.863
6.889
6.891
6.907
6.910
6.979
6.982
6.998
7.001
7.016
7.020
7.057
7.063
7.071
7.079
7.088
7.093
7.199
7.201
7.218
7.220
0.9
1
0.9
6
0.9
63.9
5
0.9
3
1.3
0
3.9
2
1.0
0
Current Data ParametersNAME MK-III-448-AEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190910Time 10.51INSTRUM spect
PROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3
NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 sec
RG 45.2DW 60.800 usecDE 6.00 usecTE 296.5 KD1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========NUC1 1H
P1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768SF 400.1300934 MHzWDW EMSSB 0LB 0.30 Hz
GB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
Figure 121: 1H-NMR spectra for compound 8e
164
Current Data Parameters
NAME MK-III-448-AEXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190910
Time 11.07INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30TD 65536
SOLVENT CDCl3NS 256
DS 4
SWH 24038.461 HzFIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 406DW 20.800 usec
DE 6.00 usec
TE 296.7 KD1 2.00000000 sec
d11 0.03000000 secDELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usecPL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dBPL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768SF 100.6127741 MHz
WDW EMSSB 0
LB 1.00 Hz
GB 0PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.15
77.47
82.14
114.94
115.15
126.35
128.46
129.09
129.67
129.75
130.48
134.76
141.46
141.49
145.62
160.87
163.32
Figure 122: 13C-NMR spectra for compound 8e
165
Figure 123: 1H-NMR spectra for compound 8f
3.54.04.55.05.56.06.57.07.58.08.59.0 ppm4.179
6.591
6.594
6.610
6.614
7.066
7.070
7.085
7.088
7.113
7.134
7.190
7.194
7.210
7.213
7.228
7.232
7.260
7.276
7.281
7.293
7.298
7.421
7.424
7.441
0.9
2
0.9
1
0.6
9
3.9
7
1.0
6
3.8
6
1.0
0
Current Data ParametersNAME MK-II-423-NEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20190612Time 12.47INSTRUM spectPROBHD 5 mm BBO BB-1HPULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9845889 secRG 362DW 60.800 usecDE 6.00 usecTE 295.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 14.35 usecPL1 -1.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300095 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} CIF_NMR 1
166
Figure 124: 13C-NMR spectra for compound 8f
180 160 140 120 100 80 60 40 20 ppm
76.84
77.15
77.47
82.22
126.98
128.49
129.15
129.36
129.97
130.94
133.81
136.50
144.11
144.95 Current Data Parameters
NAME MK-II-423-N
EXPNO 2
PROCNO 1
F2 - Acquisition Parameters
Date_ 20190614
Time 14.57
INSTRUM spect
PROBHD 5 mm BBO BB-1H
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 196
DS 4
SWH 24038.461 Hz
FIDRES 0.366798 Hz
AQ 1.3631488 sec
RG 40.3
DW 20.800 usec
DE 6.00 usec
TE 295.2 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.95 usec
PL1 -1.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG[2 waltz16
NUC2 1H
PCPD2 90.00 usec
PL12 14.95 dB
PL13 120.00 dB
PL2 -1.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127586 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
C13CPD CDCl3 {D:\CRR} CIF_NMR 1
167
Fig. S1. (a) Absorption spectra of 3aa in different acid medium (b) Absorption spectra of 3aa
with various concentration of TfOH in CHCl3
168
Fig. S2. Absorption spectra of 3aa, 3ab, 3ac, 3ah, and 3ai with TfOH in CHCl3
Fig. S3. Fluorescence spectra of 3aa, 3ac, 3ah, and 3i with TfOH in CHCl3
169
Fig. S4. Fluorescence spectra of 3a, 11a, and 13a with TfOH in CHCl3
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