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Electronic Supplementary Information

(E)-N-(Styrylsulfonyl)thiophene-2-carboxamide (4a). White solid (0.101g, 70%); m.p.140-

142oC; IR (KBr): 1326, 1138 (SO2), 1628 (C=C), 1645 (C=O), 3358 (NH) cm-1; 1H NMR (400

MHz, DMSO-d6): δ 6.60 (d, 1H, HB, J = 14.4 Hz), 6.96 (t, 1H, C4-H, J = 4.4 Hz), 7.30-7.59 (m,

6H, Ar-H & HA), 8.31-8.43 (m, 2H, C3-H & C5-H), 11.05 (bs, 1H, NH) ppm; 13C NMR (100

MHz, DMSO-d6): 126.1, 128.2, 128.5, 129.3, 129.6, 131.3, 135.4, 136.1, 136.7, 137.6

(aromatic carbons, C-HA, C-HB, C-2, C-3, C-4 & C-5), 168.7 (C=O) ppm; HRMS (m/z):

316.3456 [M+Na]; Anal. Calcd. for C13H11NO3S2: C, 53.23; H, 3.78; N, 4.77; Found: C, 53.31;

H, 3.81; N, 4.92 %.

(E)-5-Chloro-N-(styrylsulfonyl)thiophene-2-carboxamide (4b). White solid (0.116g, 72%); m.p.

147-149oC; IR (KBr): 1322, 1136 (SO2), 1635 (C=C), 1659 (C=O), 3374 (NH) cm-1; 1H NMR

(400 MHz, DMSO-d6): δ 6.58 (d, 1H, HB, J = 14.9 Hz), 6.77 (d, 1H, C4-H, J = 4.1 Hz), 7.34-

7.51 (m, 6H, Ar-H & HA), 8.13 (d, 1H, C3-H, J = 4.1 Hz), 10.23 (bs, 1H, NH) ppm; 13C NMR

(100 MHz, DMSO-d6): 125.3, 128.0, 129.2, 129.8, 131.6, 135.8, 136.4, 137.5, 140.2, 141.8

(aromatic carbons, C-HA , C-HB, C-2, C-3, C-4 & C-5), 170.1 (C=O) ppm; HRMS (m/z):

350.7861 [M+Na]; Anal. Calcd. for C13H10ClNO3S2: C, 47.63; H, 3.08; N, 4.27; Found: C, 47.74;

H, 3.13; N, 4.37%.

(E)-N-((4-Methylstyryl)sulfonyl)thiophene-2-carboxamide (4c). White solid (0.090g, 66%); m.p.


(400 MHz, DMSO-d6): δ 2.29 (s, 3H, CH3), 6.54 (d, 1H, HB, J = 14.7 Hz), 7.02 (t, 1H, C4-H, J

= 4.6 Hz), 7.15-7.42 (m, 5H, Ar-H & HA), 8.37-8.46 (m, 2H, C3-H & C5-H), 10.67 (bs, 1H, NH)

ppm; 13C NMR (100 MHz, DMSO-d6): 23.4 (CH3), 127.2, 129.0, 129.5, 130.1, 132.4, 133.8,

134.1, 136.3, 138.6, 139.1 (aromatic carbons, C-HA , C-HB, C-2, C-3, C-4 & C-5), 169.2 (C=O)

ppm; HRMS (m/z): 330.3726 [M+Na]; Anal. Calcd. for C14H13NO3S2: C, 54.71; H, 4.26; N, 4.56;

Found: C, 54.62; H, 4.28; N, 4.69%.

(E)-5-Chloro-N-((4-methylstyryl)sulfonyl)thiophene-2-carboxamide (4d). White solid (0.109g,

69%); m.p. 142-144oC; IR (KBr): 1328, 1137 (SO2), 1633 (C=C), 1650 (C=O), 3362 (NH) cm-1;

1H NMR (400 MHz, DMSO-d6): δ 2.35 (s, 3H, CH3), 6.56 (d, 1H, HB, J = 14.8 Hz), 6.85 (d, 1H,

C4-H, J = 3.8 Hz), 7.21-7.47 (m, 5H, Ar-H & HA), 8.10 (d, 1H, C3-H), 11.12 (bs, 1H, NH) ppm;

13C NMR (100 MHz, DMSO-d6): 22.8 (CH3), 126.6, 129.7, 130.5, 130.6, 133.5, 134.5, 138.1,

138.8, 139.9, 141.0 (aromatic carbons, C-HA , C-HB, C-2, C-3, C-4 & C-5), 169.9 (C=O) ppm;

HRMS (m/z): 364.8131 [M+Na]; Anal. Calcd. for C14H12ClNO3S2: C, 49.19; H, 3.54; N, 4.10;

Found: C, 49.29; H, 3.58; N, 4.27%.

. (E)-N-((4-Nitrostyryl)sulfonyl)thiophene-2-carboxamide (4e). White solid (0.09g, 73%); m.p.


(400 MHz, DMSO-d6): δ 6.61 (d, 1H, HB, J = 14.6 Hz), 7.08 (t, 1H, C4-H, J = 4.2 Hz), 7.38-7.59

(m, 5H, Ar-H & HA), 8.34-8.43 (m, 2H, C3-H & C5-H), 10.36 (bs, 1H, NH) ppm; 13C NMR (100

MHz, DMSO-d6): 124.2, 128.1, 128.6, 130.4, 131.7, 134.9, 137.2, 138.7, 141.6, 148.9 (aromatic

carbons, C-HA , C-HB, C-2, C-3, C-4 & C-5), 170.5 (C=O) ppm; HRMS (m/z): 361.3427

[M+Na]; Anal. Calcd. for C13H10N2O5S2: C, 46.15; H, 2.98; N, 8.28; Found: C, 46.25; H, 3.00; N,

8.39%.

(E)-5-Chloro-N-((4-nitrostyryl)sulfonyl)thiophene-2-carboxamide (4f). White solid (0.108g,

72%); m.p. 164-166oC; IR (KBr): 1320, 1143 (SO2), 1626 (C=C), 1681 (C=O), 3351 (NH) cm-1;

1H NMR (400 MHz, DMSO-d6): δ 6.68 (d, 1H, HB, J = 14.9 Hz), 6.88 (d, 1H, C4-H, J = 4.0 Hz),

7.49-7.70 (m, 5H, Ar-H & HA), 8.05 (d, 1H, C3-H, J = 4.0 Hz), 11.41 (bs, 1H, NH) ppm; 13C

NMR (100 MHz, DMSO-d6): 124.8, 125.7, 130.2, 130.9, 134.8, 138.4, 141.2, 141.4, 142.3,

148.3 (aromatic carbons, C-HA , C-HB, C-2, C-3, C-4 & C-5), 171.1 (C=O) ppm; HRMS (m/z):

395.7825 [M+Na]; Anal. Calcd. for C13H9ClN2O5S2: C, 41.88; H, 2.43; N, 7.51; Found: C, 42.02;

H, 2.48; N, 7.66%.

N-((1,3,5-Triphenyl-4,5-dihydro-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamide (5a)

Yellow solid (0.168g, 68%); m.p. 161-163oC; IR (KBr): 1336, 1133 (SO2), 1577 (C=N), 1630

(C=C), 1674 (C=O), 3374 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 5.09 (d, 1H, C4ʹ-H,

J = 7.2 Hz), 5.43 (d, 1H, C5ʹ-H, J =7.2 Hz), 7.04 (t, 1H, C4-H, J = 4.8 Hz), 7.23-7.88 (m, 15H,

Ar-H), 8.39-8.44 (m, 2H, C3-H & C5-H), 10.51 (bs, 1H, NH) ppm; 13C NMR (100 MHz, DMSO-

d6): 62.7 (C-4ʹ), 86.8 (C-5ʹ), 116.9, 120.4, 126.5, 126.7, 128.1, 129.1, 129.5, 129.8, 130.3, 130.7,

133.3, 135.5, 135.6, 136.7, 144.4, 144.9 (aromatic carbons, C-2, C-3, C-4 & C-5), 154.8 (C-3ʹ),

169.3 (C=O) ppm; HRMS (m/z): 510.5824 [M+Na]; Anal. Calcd. for C26H21N3O3S2: C, 64.05; H,

4.34; N, 8.62; Found: C, 64.17; H, 4.40; N, 8.79%.

5-Chloro-N-((1,3,5-triphenyl-4,5-dihydro-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamide

(5b). Yellow solid (0.189g, 71%); m.p. 166-168oC; IR (KBr): 1327, 1135 (SO2), 1605 (C=N),

1622 (C=C), 1652 (C=O), 3380 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 5.12 (d, 1H, C4ʹ-

H, J = 7.1 Hz), 5.49 (d, 1H, C5ʹ-H, J =7.1 Hz), 6.72 (d, 1H, C4-H, J = 3.9 Hz), 7.37-7.84 (m,

15H, Ar-H), 8.02 (d, 1H, C3-H, J = 3.9 Hz), 11.24 (bs, 1H, NH) ppm; 13C NMR (100 MHz,

DMSO-d6): 61.8 (C-4ʹ), 87.4 (C-5ʹ), 116.4, 121.2, 126.2, 127.0, 128.9, 130.5, 131.2, 131.9,

132.7, 134.4, 135.2, 135.8, 139.6, 143.1, 143.2, 145.1 (aromatic carbons, C-2, C-3, C-4 & C-5),

155.6 (C-3ʹ), 168.4 (C=O) ppm; HRMS (m/z): 545.0244 [M+Na]; Anal. Calcd. for

C26H20ClN3O3S2: C, 59.82; H, 3.86; N, 8.05; Found: C, 59.93; H, 3.89; N, 8.16%.

N-((1,3-Diphenyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamide

(5c). Yellow solid (0.172g, 67%); m.p. 165-167; IR (KBr): 1333, 1142 (SO2), 1583 (C=N), 1634

(C=C), 1681 (C=O), 3375 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 2.41 (s, 3H, CH3), 5.05

(d, 1H, C4ʹ-H, J = 7.6 Hz), 5.41 (d, 1H, C5ʹ-H, J = 7.6 Hz), 6.99 (t, 1H, C4-H, J = 4.2 Hz), 7.19-

7.76 (m, 14H, Ar-H), 8.38-8.41 (m, 2H, C3-H & C5-H), 10.73 (bs, 1H, NH) ppm; 13C NMR (100

MHz, DMSO-d6): 23.7 (CH3), 62.2 (C-4ʹ), 86.3 (C-5ʹ), 117.3, 120.7, 125.9, 128.4, 128.5, 129.7,

130.1, 130.8, 132.1, 132.5, 134.3, 136.1, 136.4, 136.6, 140.1, 144.1 (aromatic carbons, C-2, C-3,

C-4 & C-5), 154.2 (C-3ʹ), 171.2 (C=O) ppm; HRMS (m/z): 524.6071 [M+Na]; Anal. Calcd. for

C27H23N3O3S2: C, 64.65; H, 4.62; N, 8.38; Found: C, 64.79; H, 4.65; N, 8.50%.

5-Chloro-N-((1,3-diphenyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-4-yl)sulfonyl)thiophene-2-

carboxamide (5d). Yellow solid (0.199g, 73%); m.p. 175-177; IR (KBr): 1335, 1149 (SO2), 1619

(C=N), 1638 (C=C), 1684 (C=O), 3369 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 2.37

(s, 3H, CH3), 4.97 (d, 1H, C4ʹ-H, J = 7.5 Hz), 5.51 (d, 1H, C5ʹ-H, J =7.5 Hz), 6.80 (d, 1H, C4-H,

J = 4.0 Hz), 7.16-7.89 (m, 14H, Ar-H), 8.11 (d, 1H, C3-H, J = 4.0 Hz), 11.09 (bs, 1H, NH) ppm;

13C NMR (100 MHz, DMSO-d6): 24.1 (CH3), 61.5 (C-4ʹ), 85.8 (C-5ʹ), 117.8, 121.5, 126.3, 128.7,

129.2, 129.6, 130.4, 130.6, 133.8, 135.5, 135.8, 136.3, 140.5, 141.8, 142.6, 144.6 (aromatic

carbons, C-2, C-3, C-4 & C-5), 154.5 (C-3ʹ), 170.6 (C=O) ppm; HRMS (m/z): 559.0499

[M+Na]; Anal. Calcd. for C27H22ClN3O3S2: C, 60.50; H, 4.14; N, 7.84; Found: C, 60.59; H, 4.19;

N, 7.89%.

N-((5-(4-Nitrophenyl)-1,3-diphenyl-4,5-dihydro-1H-pyrazol-4-yl)sulfonyl)thiophene-2-

carboxamide (5e).

Yellow solid (0.190g, 70%); m.p. 170-172; IR (KBr): 1342, 1146 (SO2), 1598 (C=N), 1637


J = 7.8 Hz), 5.46 (d, 1H, C5ʹ-H, J =7.8 Hz), 7.01 (t, 1H, C4-H, J = 4.3 Hz), 7.34-7.80 (m, 14H,


d6): 62.9 (C-4ʹ), 87.1 (C-5ʹ), 116.2, 120.6, 123.0, 123.9, 128.3, 128.8, 130.9, 131.2, 131.6, 133.4,


170.9 (C=O) ppm; HRMS (m/z): 555.5794 [M+Na]; Anal. Calcd. for C26H20N4O5S2: C, 58.64; H,

3.79; N, 10.52; Found: C, 58.75; H, 3.82; N, 10.65%.

5-Chloro-N-((5-(4-nitrophenyl)-1,3-diphenyl-4,5-dihydro-1H-pyrazol-4-yl)sulfonyl)thiophene

-2-carboxamide (5f). Yellow solid (0.205g, 71%); m.p. 183-185; IR (KBr): 1329, 1134 (SO2),

1590 (C=N), 1627 (C=C), 1677 (C=O), 3368 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 4.99

(d, 1H, C4ʹ-H, J = 7.6 Hz), 5.40 (d, 1H, C5ʹ-H, J = 7.6 Hz), 6.84 (d, 1H, C4-H, J = 4.1 Hz), 7.45-

7.99 (m, 14H, Ar-H), 8.16 (d, 1H, C3-H, J = 4.1 Hz), 11.17 (bs, 1H, NH) ppm; 13C NMR (100

MHz, DMSO-d6): 61.7 (C-4ʹ), 87.9 (C-5ʹ), 117.5, 121.8, 123.6, 124.2, 128.7, 129.4, 130.3, 131.1,

132.9, 135.4, 136.0, 140.3, 143.2, 143.5, 145.9, 149.7 (aromatic carbons, C-2, C-3, C-4 & C-5),

155.1 (C-3ʹ), 168.6 (C=O) ppm; HRMS (m/z): 590.0216 [M+Na]; Anal. Calcd. for


N-((3,5-Diphenyl-4,5-dihydroisoxazol-4-yl)sulfonyl)thiophene-2-carboxamide (6a). Yellow solid

(0.224g, 66%); m.p. 163-165; IR (KBr): 1328, 1140 (SO2), 1624 (C=N), 1631 (C=C), 1671

(C=O), 3392 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 5.05 (d, 1H, C4ʹ-H, J = 6.8 Hz), 5.65

(d, 1H, C5ʹ-H, J = 6.8 Hz), 6.92 (t, 1H, C4-H, J = 4.4 Hz), 7.37-7.77 (m, 10H, Ar-H), 8.32-8.42

(m, 2H, C3-H & C5-H), 11.26 (bs, 1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6): 60.4 (C-4ʹ),

84.3 (C-5ʹ), 127.0, 128.5, 128.8, 128.9, 129.6, 131.6, 132.3, 132.6, 134.6, 136.4, 137.8, 140.6

(aromatic carbons, C-2, C-3, C-4 & C-5), 165.2 (C-3ʹ), 170.3 (C=O) ppm; HRMS (m/z):

435.4668 [M+Na]; Anal. Calcd. for C20H16N2O4S2: C, 58.24; H, 3.91; N, 6.79; Found: C, 58.35;

H, 3.93; N, 6.95%.

5-Chloro-N-((3,5-diphenyl-4,5-dihydroisoxazol-4-yl)sulfonyl)thiophene-2-carboxamide (6b).



J = 7.7 Hz), 5.74 (d, 1H, C5ʹ-H, J =7.7 Hz), 6.75 (d, 1H, C4-H, J = 4.0 Hz), 7.26-7.73 (m, 10H,

Ar-H), 8.17 (d, 1H, C3-H, J = 4.0 Hz), 10.42 (bs, 1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6):

60.1 (C-4ʹ), 83.6 (C-5ʹ), 127.5, 128.1, 129.6, 129.7, 130.8, 131.8, 133.1, 135.7, 135.9, 140.1,

141.2, 142.1 (aromatic carbons, C-2, C-3, C-4 & C-5), 166.1 (C-3ʹ), 171.7 (C=O) ppm; HRMS

(m/z): 469.9089 [M+Na]; Anal. Calcd. for C20H15ClN2O4S2: C, 53.75; H, 3.38; N, 6.27; Found: C,

53.88; H, 3.42; N, 6.40%.

N-((3-Phenyl-5-(p-tolyl)-4,5-dihydroisoxazol-4-yl)sulfonyl)thiophene-2-carboxamide (6c).



(d, 1H, C4ʹ-H, J = 7.4 Hz), 5.70 (d, 1H, C5ʹ-H, J = 7.4 Hz), 7.03 (t, 1H, C4-H, J = 4.4 Hz),

7.16-7.82 (m, 9H, Ar-H), 8.33-8.45 (m, 2H, C3-H & C5-H), 10.53 (bs, 1H, NH) ppm; 13C NMR

(100 MHz, DMSO-d6): 24.3 (CH3), 61.1 (C-4ʹ), 84.9 (C-5ʹ), 125.2, 125.3, 128.1, 128.5, 129.7,

130.2, 131.8, 132.4, 135.2, 136.8, 138.1, 138.5 (aromatic carbons, C-2, C-3, C-4 & C-5), 165.8

(C-3ʹ), 171.3 (C=O) ppm; HRMS (m/z): 449.4958 [M+Na]; Anal. Calcd. for C21H18N2O4S2: C,

59.14; H, 4.25; N, 6.57; Found: C, 59.24; H, 4.30; N, 6.67%.

5-Chloro-N-((3-phenyl-5-(p-tolyl)-4,5-dihydroisoxazol-4-yl)sulfonyl)thiophene-2-carboxamide

(6d). Yellow solid (0.263g, 69%); m.p. 173-175; IR (KBr): 1334, 1142 (SO2), 1576 (C=N), 1632


(d, 1H, C4ʹ-H, J = 7.3 Hz), 5.60 (d, 1H, C5ʹ-H, J = 7.3 Hz), 6.73 (d, 1H, C4-H, J = 3.9 Hz), 7.22-

7.79 (m, 9H, Ar-H), 8.08 (d, 1H, C3-H, J = 3.9 Hz), 11.07 (bs, 1H, NH) ppm; 13C NMR (100

MHz, DMSO-d6): 22.3 (CH3), 61.3 (C-4ʹ), 84.0 (C-5ʹ), 124.9, 129.3, 130.0, 130.1, 130.5, 132.8,


169.4 (C=O) ppm; HRMS (m/z): 483.9359 [M+Na]; Anal. Calcd. for C21H17ClN2O4S2: C, 54.72;

H, 3.72; N, 6.08; Found: C, 54.64; H, 3.75; N, 6.25%.

N-((5-(4-Nitrophenyl)-3-phenyl-4,5-dihydroisoxazol-4-yl)sulfonyl)thiophene-2-carboxamide

(6e). Yellow solid (0.249g, 66%); m.p. 165-167; IR (KBr): 1318, 1130 (SO2), 1580 (C=N), 1637


J = 7.6 Hz), 5.77 (d, 1H, C5ʹ-H, J =7.6 Hz), 6.95 (t, 1H, C4-H, J = 4.3 Hz), 7.37-7.84 (m, 9H, Ar-

H), 8.38-8.43 (m, 2H, C3-H & C5-H), 11.19 (bs, 1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6):

60.9 (C-4ʹ), 83.1 (C-5ʹ), 125.6, 128.3, 128.9, 129.8, 130.5, 131.4, 133.5, 134.4, 135.5, 136.1,

145.9, 146.8 (aromatic carbons, C-2, C-3, C-4 & C-5), 165.6 (C-3ʹ), 172.3 (C=O) ppm; HRMS

(m/z): 480.4641 [M+Na]; Anal. Calcd. for C20H15N3O6S2: C, 52.51; H, 3.31; N, 9.19; Found: C,

52.61; H, 3.33; N, 9.31%.

5-Chloro-N-((5-(4-nitrophenyl)-3-phenyl-4,5-dihydroisoxazol-4-yl)sulfonyl)thiophene-2-

carboxamide (6f). Yellow solid (0.276g, 68%); m.p. 180-182; IR (KBr): 1345, 1135 (SO2), 1572

(C=N), 1642 (C=C), 1664 (C=O), 3383 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 5.16 (d,

1H, C4ʹ-H, J = 7.9 Hz), 5.63 (d, 1H, C5ʹ-H, J = 7.9 Hz), 6.83 (d, 1H, C4-H, J = 4.1 Hz), 7.42-7.92

(m, 9H, Ar-H), 8.05 (d, 1H, C5-H, J = 4.1 Hz), 11.43 (bs, 1H, NH) ppm; 13C NMR (100 MHz,

DMSO-d6): 61.3 (C-4ʹ), 85.2 (C-5ʹ), 124.1, 127.4, 129.4, 130.1, 131.6, 133.2, 135.2, 136.2,

139.4, 143.3, 146.3, 147.6 (aromatic carbons, C-2, C-3, C-4 & C-5), 166.5 (C-3ʹ), 168.3 (C=O)

ppm; HRMS (m/z): 514.9075 [M+Na]; Anal. Calcd. for C20H14ClN3O6S2: C, 48.83; H, 2.87; N,

8.54; Found: C, 48.92; H, 2.92; N, 8.68%.

N-((1,3,5-Triphenyl-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamide (7a). Yellow solid

(0.071g, 71%); m.p. 174-176; IR (KBr): 1351, 1149 (SO2), 1568 (C=N), 1628 (C=C), 1662

(C=O), 3370 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 6.93 (t, 1H, C4-H, J = 4.8 Hz),

7.22-7.68 (m, 15H, Ar-H), 8.36-8.45 (m, 2H, C3-H & C5-H), 10.61 (bs, 1H, NH) ppm; 13C NMR

(100 MHz, DMSO-d6): 121.2 (C-4ʹ), 125.1, 124.3, 126.5, 127.5, 128.1, 128.3, 128.8, 129.2,

129.6, 131.6, 132.2, 132.4, 133.4, 135.6, 137.3, 139.8, 141.8 (aromatic carbons, C-2, C-3, C-4,

C-5 & C-5ʹ), 156.7 (C-3ʹ), 170.7 (C=O) ppm; HRMS (m/z): 508.5671 [M+Na]; Anal. Calcd. for


5-Chloro-N-((1,3,5-triphenyl-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamide (7b).


(C=C), 1650 (C=O), 3368 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 6.81 (d, 1H, C4-H, J

= 3.8 Hz), 7.28-7.74 (m, 15H, Ar-H), 8.15 (d, 1H, C3-H, J = 3.8 Hz), 10.12 (bs, 1H, NH) ppm;

13C NMR (100 MHz, DMSO-d6): 121.5 (C-4ʹ), 123.1, 126.2, 127.0, 127.5, 127.8, 128.0, 129.4,


C-4, C-5 & C-5ʹ), 156.7 (C-3ʹ), 168.1 (C=O) ppm; HRMS (m/z): 543.0067 [M+Na]; Anal. Calcd.

for C26H18ClN3O3S2: C, 60.05; H, 3.49; N, 8.08; Found: C, 60.13; H, 3.54; N, 8.24%.

N-((1,3-Diphenyl-5-(p-tolyl)-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamide (7c).



(t, 1H, C4-H, J = 4.4 Hz), 7.18-7.81 (m, 14H, Ar-H), 8.34-8.42 (m, 2H, C3-H & C5-H), 10.36

(bs, 1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6): 24.6 (CH3), 120.9 (C-4ʹ), 124.9, 125.8, 126.3,

126.8, 127.1, 128.3, 129.3, 129.8, 130.3, 130.6, 131.9, 132.9, 133.2, 134.0, 136.5, 140.3, 141.3,

(aromatic carbons, C-2, C-3, C-4, C-5 & C-5ʹ), 155.2 (C-3ʹ), 169.6 (C=O) ppm; HRMS (m/z):

522.5935 [M+Na]; Anal. Calcd. for C27H21N3O3S2: C, 64.91; H, 4.24; N, 8.41; Found: C, 65.13;

H, 4.26; N, 8.53%.

5-Chloro-N-((1,3-diphenyl-5-(p-tolyl)-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamide (7d).



(d, 1H, C4-H, J = 4.1 Hz), 7.11-7.95 (m, 14H, Ar-H), 8.04 (d, 1H, C3-H, J = 4.1 Hz), 11.28 (bs,

1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6): 23.1 (CH3), 121.7 (C-4ʹ), 123.3, 125.1, 125.7,

126.4, 127.6, 128.0, 129.5, 129.7, 131.0, 131.2, 132.2, 132.6, 134.9, 139.5, 140.8, 141.0, 143.5

(aromatic carbons, C-2, C-3, C-4, C-5 & C-5ʹ), 157.1 (C-3ʹ), 172.5 (C=O) ppm; HRMS (m/z):

557.0356 [M+Na]; Anal. Calcd. for C27H20ClN3O3S2: C, 60.72; H, 3.77; N, 7.87; Found: C,

60.81; H, 3.81; N, 8.05%.

N-((5-(4-Nitrophenyl)-1,3-diphenyl-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamide (7e).


(C=C), 1672 (C=O), 3365 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 6.97 (t, 1H, C4-H,

J = 4.2 Hz), 7.39-7.85 (m, 14H, Ar-H), 8.35-8.46 (m, 2H, C3-H & C5-H), 10.82 (bs, 1H, NH)

ppm; 13C NMR (100 MHz, DMSO-d6): 120.1 (C-4ʹ), 124.6, 124.8, 126.1, 126.9, 127.3, 127.4,

129.4, 129.8, 130.4, 131.4, 132.0, 135.3, 137.9, 139.7, 140.4, 140.9, 146.2 (aromatic carbons, C-2,

C-3, C-4, C-5 & C-5ʹ), 157.6 (C-3ʹ), 171.0 (C=O) ppm; HRMS (m/z): 553.5618 [M+Na]; Anal.

Calcd. for C26H18N4O5S2: C, 58.86; H, 3.42; N, 10.56; Found: C, 58.99; H, 3.47; N, 10.69%.

5-Chloro-N-((5-(4-nitrophenyl)-1,3-diphenyl-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamide

(7f). Yellow solid (0.070g, 70%); m.p. 202-204; IR (KBr): 1348, 1147 (SO2), 1565 (C=N), 1640

(C=C), 1660 (C=O), 3362 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 6.86 (d, 1H, C4-H,

J = 3.9 Hz), 7.44-7.78 (m, 14H, Ar-H), 8.19 (d, 1H, C3-H, J = 3.9 Hz), 11.39 (bs, 1H, NH) ppm;

13C NMR (100 MHz, DMSO-d6): 120.6 (C-4ʹ), 123.5, 124.1, 126.9, 127.2, 127.5, 127.9, 129.2,

130.6, 130.7, 133.5, 135.0, 139.1, 140.7, 141.2, 141.3, 142.2, 146.7 (aromatic carbons, C-2, C-3, C-

4, C-5 & C-5ʹ), 157.3 (C-3ʹ), 172.5 (C=O) ppm; HRMS (m/z): 588.0038 [M+Na]; Anal. Calcd. for


N-((3,5-Diphenylisoxazol-4-yl)sulfonyl)thiophene-2-carboxamide (8a). Yellow solid (0.071g,

71%); m.p. 179-181; IR (KBr): 1329, 1141 (SO2), 1592 (C=N), 1625 (C=C), 1655 (C=O), 3356

(NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 6.91 (t, 1H, C4-H, J = 4.4 Hz), 7.33-7.90 (m, 10H,


d6): 101.2 (C-4ʹ), 125.6, 126.6, 126.8, 127.4, 129.8, 129.9, 130.1, 130.7, 131.3, 133.7, 134.2, 136.2

(aromatic carbons, C-2, C-3, C-4 & C-5), 151.7 (C-3ʹ), 158.4 (C-5ʹ), 172.4 (C=O) ppm; HRMS

(m/z): 433.4514 [M+Na]; Anal. Calcd. for C20H14N2O4S2: C, 58.52; H, 3.43; N, 6.82; Found: C,

58.63; H, 3.49; N, 6.93%.

5-Chloro-N-((3,5-diphenylisoxazol-4-yl)sulfonyl)thiophene-2-carboxamide (8b). Yellow solid

(0.073g, 73%); m.p. 168-170; IR (KBr): 1324, 1150 (SO2), 1575 (C=N), 1621 (C=C), 1673

(C=O), 3370 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 6.80 (d, 1H, C4-H, J = 3.9 Hz), 7.31-

7.83 (m, 10H, Ar-H), 8.07 (d, 1H, C3-H, J = 3.9 Hz), 11.15 (bs, 1H, NH) ppm; 13C NMR

(100 MHz, DMSO-d6): 102.7 (C-4ʹ), 126.4, 127.0, 127.1, 128.5, 129.2, 130.7, 131.5, 131.7,

133.4, 134.3, 140.7, 142.8 (aromatic carbons, C-2, C-3, C-4 & C-5), 152.5 (C-3ʹ), 159.7 (C-5ʹ),

168.2 (C=O) ppm; HRMS (m/z): 467.8945 [M+Na]; Anal. Calcd. for C20H13ClN2O4S2: C, 53.99;

H, 2.95; N, 6.30; Found: C, 53.89; H, 2.97; N, 6.46%.

N-((3-Phenyl-5-(p-tolyl)isoxazol-4-yl)sulfonyl)thiophene-2-carboxamide (8c). Yellow solid

(0.072g, 72%); m.p. 188-191; IR (KBr): 1343, 1131 (SO2), 1601 (C=N), 1632 (C=C), 1684

(C=O), 3351 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 2.44 (s, 3H, CH3), 7.05 (t, 1H, C4-H,

J = 4.2 Hz), 7.20-7.78 (m, 9H, Ar-H), 8.38-8.45 (m, 2H, C3-H & C5-H), 11.32 (bs, 1H, NH) ppm;

13C NMR (100 MHz, DMSO-d6): 22.9 (CH3), 102.2 (C-4ʹ), 125.1, 126.2, 127.4, 128.5, 128.7,

130.2, 130.5, 131.1, 131.5, 132.5, 135.1, 137.4 (aromatic carboms, C-2, C-3, C-4 & C-5), 152.2

(C-3ʹ), 158.3 (C-5ʹ), 171.5 (C=O) ppm; HRMS (m/z): 447.4779 [M+Na]; Anal. Calcd. for


5-Chloro-N-((3-phenyl-5-(p-tolyl)isoxazol-4-yl)sulfonyl)thiophene-2-carboxamide (8d).



(d, 1H, C4-H, J = 4.0 Hz), 7.17-7.72 (m, 9H, Ar-H), 6.87 (d, 1H, C3-H, J = 4.0 Hz), 10.14

(bs, 1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6): 24.5 (CH3), 101.5 (C-4ʹ), 126.4, 126.8,


C-4 & C-5), 153.5 (C-3ʹ), 159.8 (C-5ʹ), 172.8 (C=O) ppm; HRMS (m/z): 481.9219 [M+Na];

Anal. Calcd. for C21H15ClN2O4S2: C, 54.96; H, 3.29; N, 6.10; Found: C, 55.04; H, 3.34; N,

6.20%.

N-((5-(4-Nitrophenyl)-3-phenylisoxazol-4-yl)sulfonyl)thiophene-2-carboxamide (8e).


(C=C), 1674 (C=O), 3378 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 6.92 (t, 1H, C4-H,

J = 4.6 Hz), 7.47-7.96 (m, 9H, Ar-H), 8.32-8.41 (m, 2H, C3-H & C5-H), 11.57 (bs, 1H, NH) ppm;

13C NMR (100 MHz, DMSO-d6): 101.9 (C-4ʹ), 123.9, 124.7, 126.5, 128.3, 129.2, 130.1, 130.5,

132.1, 135.9, 136.3, 138.9, 147.5 (aromatic carbons, C-2, C-3, C-4 & C-5), 151.8 (C-3ʹ), 159.1

(C-5ʹ), 172.6 (C=O) ppm; HRMS (m/z): 478.4497 [M+Na]; Anal. Calcd. for C20H13N3O6S2: C,

52.74; H, 2.88; N, 9.23; Found: C, 52.83; H, 2.91; N, 9.36%.

5-Chloro-N-((5-(4-nitrophenyl)-3-phenylisoxazol-4-yl)sulfonyl)thiophene-2-carboxamide (8f).


(C=C), 1688 (C=O), 3361 (NH) cm-1; 1H NMR (400 MHz, DMSO-d6): δ 6.74 (d, 1H, C4-H, J

= 4.1 Hz), 7.38-7.75 (m, 9H, Ar-H), 8.09 (d, 1H, C5-H, J = 4.1 Hz), 10.65 (bs, 1H, NH) ppm; 13C

NMR (100 MHz, DMSO-d6): 102.1 (C-4ʹ), 124.1, 124.8, 127.1, 128.9, 131.4, 131.8, 132.8,

134.7, 136.9, 141.1, 141.3, 147.0 (aromatic carbons, C-2, C-3, C-4 & C-5), 152.9 (C-3ʹ), 158.6

(C-5ʹ), 169.0 (C=O) ppm; HRMS (m/z): 512.8914 [M+Na]; Anal. Calcd. for C20H12ClN3O6S2: C,

49.03; H, 2.47; N, 8.58; Found: C, 49.17; H, 2.53; N, 8.75%.

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