New Method for Synthesis of 3-Arylindolizines from Electron-Deficient Alkynes through 1, 3-Dipolar Cycloaddition

doi:10.6023/cjoc201401001

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 903-908.DOI: 10.6023/cjoc201401001 Previous Articles Next Articles

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以缺电子炔烃为原料经1,3-偶极环加成反应合成3-芳基中氮茚的新方法

李国栋^a,b, 胡华友^a,b, 阚玉和^a,b, 马奎蓉^b

a 东北师范大学化学学院长春 130024;
b 淮阴师范学院化学化工学院淮安 223300

收稿日期:2014-01-03 修回日期:2014-01-26 发布日期:2014-02-12
通讯作者: 胡华友，阚玉和 E-mail:njuhhy@hotmail.com;kyh@hytc.edu.cn
基金资助:
国家自然科学基金（No.21202058）、江苏省自然科学基金（No.BK2011408）、江苏省高校重大（No. 13KJA150001）资助项目.

New Method for Synthesis of 3-Arylindolizines from Electron-Deficient Alkynes through 1, 3-Dipolar Cycloaddition

Li Guodong^a,b, Hu Huayou^a,b, Kan Yuhe^a,b, Ma Kuirong^b

a Department of Chemistry, Northeast Normal University, Changchun 130024;
b School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300

Received:2014-01-03 Revised:2014-01-26 Published:2014-02-12
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21202058), the Natural Science Foundation of Jiangsu Province (No. BK2011408), and the Department of Education of Jiangsu Province (No. 13KJA150001).

1. New Method for Synthesis of 3-Arylindolizines from Electron-Deficient Alkynes through 1, 3-Dipolar Cycloaddition.PDF(304KB)

Abstract

A novel and efficient procedure for the preparation of 3-aryl-indolizine by 1,3-dipolar cycloaddition was established. The pyridinium salts were prepared from the corresponding pyridines and benzyl halides. In the presence of cesium carbonate, electron-deficient alkynes reacted with the pyridinium salts in 1,4-dioxane through 1,3-dipolar cycloaddition followed by an aromatization reaction to generate the corresponding 3-aryl-indolizines. This method features cheap reagents, a simple workup procedure, mild conditions, high regioselectivity and generating the desired products in moderate to high yield (34%～81%).

Key words: indolizine, 1,3-dipolar cycloaddition, electron-deficient alkyne

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Li Guodong, Hu Huayou, Kan Yuhe, Ma Kuirong. New Method for Synthesis of 3-Arylindolizines from Electron-Deficient Alkynes through 1, 3-Dipolar Cycloaddition[J]. Chin. J. Org. Chem., 2014, 34(5): 903-908.

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以缺电子炔烃为原料经1,3-偶极环加成反应合成3-芳基中氮茚的新方法

New Method for Synthesis of 3-Arylindolizines from Electron-Deficient Alkynes through 1, 3-Dipolar Cycloaddition

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