Synthesis of 3-Unsubstituted Indolizines from Electron Deficient Alkenes under Transition Metal Free Conditions

doi:10.6023/cjoc201509044

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (2): 330-335.DOI: 10.6023/cjoc201509044 Previous Articles Next Articles

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无过渡金属存在下从缺电子烯烃出发合成3位未取代的中氮茚

胡华友^a,b, 李国栋^b, 顾宁^a, 吉民^a

a 东南大学生物科学与医学工程学院南京 210096;
b 淮阴师范学院化学化工学院淮安 223300

收稿日期:2015-09-30 修回日期:2015-10-26 发布日期:2015-11-03
通讯作者: 顾宁 E-mail:njuhhy@hotmail.com
基金资助:
国家自然科学基金(No. 21202058)、江苏省高校重大(No. 13KJA150001)、中国博士后基金(Nos. 2012M511645, 2013T60483)资助项目

Synthesis of 3-Unsubstituted Indolizines from Electron Deficient Alkenes under Transition Metal Free Conditions

Hu Huayou^a,b, Li Guodong^b, Gu Ning^a, Ji Min^a

a School of Biological Science and Medical Engineering, Southeast University, Nanjing 210096;
b School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300

Received:2015-09-30 Revised:2015-10-26 Published:2015-11-03
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21202058), the Department of Education of Jiangsu Province (No. 13KJA150001), the China Postdoctoral Science Foundation (Nos. 2012M511645, 2013T60483).

1. Synthesis of 3-Unsubstituted Indolizines from Electron Deficient Alkenes under Transition Metal Free Conditions.PDF(395KB)

Abstract

3-Unsubstituted indolizine not only exhibits a variety of important biological activities, but also is a kind of important intermediate in organic synthesis. A transition metal free method for synthesizing 3-unsubstituted indolizines from pyridines, 2-chloroacetic acid and electron deficient alkenes has been invented in this paper. The designed products were obtained via oxidative dehydrogenation and decarboxylation reactions, and 2,2,6,6-tetramthyl-1-piperidinyloxy (TEMPO) was used as an oxidant. This method featured simple procedure, easy available starting materials and transition metal free conditions.

Key words: indolizine, 2,2,6,6-tetramthyl-1-piperidinyloxy, 1,3-dipolar cycloaddition, transition metal free reaction, dehydroaromatization

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Hu Huayou, Li Guodong, Gu Ning, Ji Min . Synthesis of 3-Unsubstituted Indolizines from Electron Deficient Alkenes under Transition Metal Free Conditions[J]. Chin. J. Org. Chem., 2016, 36(2): 330-335.

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无过渡金属存在下从缺电子烯烃出发合成3位未取代的中氮茚

Synthesis of 3-Unsubstituted Indolizines from Electron Deficient Alkenes under Transition Metal Free Conditions

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