Supporting Information · Metal-Free Tandem Cycloaddition Strategy for the Synthesis of Indolizines...
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- 1 - Supporting Information Metal-Free Tandem Cycloaddition Strategy for the Synthesis of Indolizines from Pyridine Derivatives and γ-Bromo-Crotonates under Mild Conditions Yanqiu Li, a Bingchuan Yang, a Yan Sun, a Huayi Wang, a Huipeng Li, a Shuai Fang, a Xiaoyi Niu, a and Chen Ma a,b * a School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P R China b State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, 100191, P R China. E-mail: [email protected] Contents 1. Crystal data of compound 3b P2 2. 1 H NMR, 13 C NMR, and HRMS spectra data of the products P2-P27 Appendix Spectral Copies of 1 H NMR, 13 C NMR and HRMS of Compounds Obtained in this Study Electronic Supplementary Material (ESI) for RSC Advances This journal is © The Royal Society of Chemistry 2013
Transcript of Supporting Information · Metal-Free Tandem Cycloaddition Strategy for the Synthesis of Indolizines...
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Supporting Information
Metal-Free Tandem Cycloaddition Strategy for the Synthesis of
Indolizines from Pyridine Derivatives and γ-Bromo-Crotonates
under Mild Conditions
Yanqiu Li,a Bingchuan Yang,a Yan Sun,a Huayi Wang,a Huipeng Li,a Shuai Fang,a Xiaoyi
Niu,a and Chen Maa,b*
aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P R China bState Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, 100191, P R China. E-mail: [email protected]
Contents 1. Crystal data of compound 3b P2 2. 1H NMR, 13C NMR, and HRMS spectra data of the products P2-P27
Appendix Spectral Copies of 1H NMR, 13C NMR and HRMS of Compounds Obtained in this Study
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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Table S1. Details of Crystal Structure Determination for 3b. Compound 3b
Chemical formula C22H21NO4
Formula Mass 363.40
Crystal system Triclinic
a/Å 7.5360(5)
b/Å 8.5400(6)
c/Å 15.3432(11)
α/° 74.7452(7)
β/° 77.1894(8)
γ/° 83.1256(8)
Unit cell volume/Å3 926.97(11)
Temperature/K 293(2)
Space group P1̄
No. of formula units per unit cell, Z 2
No. of reflections measured 10932
No. of independent reflections 4200
Rint 0.0205
Final R1 values (I > 2σ(I)) 0.0399
Final wR(F2) values (I > 2σ(I)) 0.0948
Final R1 values (all data) 0.0575
Final wR(F2) values (all data) 0.1048
NO
OO
O3a
NO
OO
O3a
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NO
OO
O3a
NO
OO
O3a
NO
OO
O3a
NO
OO
O3a
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NO
O
OO
3b
NO
O
OO
3b
NO
O
OO
3b
NO
O
OO
3b
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NO
O
OO
3b
NO
O
OO
3b
NO
O
OO
3c
NO
O
OO
3c
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NO
O
OO
3c
NO
O
OO
3c
NO
O
OO
3c
NO
O
OO
3c
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NO
O
OO 3d
NO
O
OO 3d
NO
O
OO 3d
NO
O
OO 3d
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NO
O
OO 3d
NO
O
OO 3d
NO
O
OO 3e
NO
O
OO 3e
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
O
OO 3e
NO
O
OO 3e
NO
O
OO 3e
NO
O
OO 3e
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NO
O
OO 3f
NO
O
OO 3f
NO
O
OO 3f
NO
O
OO 3f
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NO
O
OO 3f
NO
O
OO 3f
NO
O
OO 3g
NO
O
OO 3g
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
O
OO 3g
NO
O
OO 3g
NO
O
OO 3g
NO
O
OO 3g
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
O
OO 3h
NO
O
OO 3h
NO
O
OO 3h
NO
O
OO 3h
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
O
OO 3h
NO
O
OO 3h
NO
O
OO 3i
NO
O
OO 3i
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
O
OO 3i
NO
O
OO 3i
NO
O
OO 3i
NO
O
OO 3i
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
O
OO
Cl
3j
NO
O
OO
Cl
3j
NO
O
OO
Cl
3j
NO
O
OO
Cl
3j
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
O
OO
Cl
3j
NO
O
OO
Cl
3j
NO
O
OO 3k
NO
O
OO 3k
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
O
OO 3k
NO
O
OO 3k
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O
OO 3k
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OO 3k
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
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OO 3l
NO
O
OO 3l
NO
O
OO 3l
NO
O
OO 3l
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
O
OO 3l
NO
O
OO 3l
NO
O
OO
3m
NO
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OO
3m
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NO
O
OO
3m
NO
O
OO
3m
NO
O
OO
3m
NO
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3m
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NO
O
OO 3n
NO
O
OO 3n
NO
O
OO 3n
NO
O
OO 3n
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NO
O
OO 3n
NO
O
OO 3n
NO
O
OO 3o
NO
O
OO 3o
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NO
O
OO 3o
NO
O
OO 3o
NO
O
OO 3o
NO
O
OO 3o
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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NO
O
OO 3p
NO
O
OO 3p
NO
O
OO 3p
NO
O
OO 3p
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NO
O
OO 3p
NO
O
OO 3p
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NO
OO
O3a
NO
OO
O3a
Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013
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