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

doi:10.6023/cjoc201401001

有机化学 ›› 2014, Vol. 34 ›› Issue (5): 903-908.DOI: 10.6023/cjoc201401001 上一篇下一篇

研究论文

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).

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1. 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.PDF(304KB)

摘要/Abstract

报道了一种简便有效地合成3-芳基中氮茚的方法. 反应需要的吡啶鎓盐可以用吡啶和苄卤很容易制得，然后以1，4-二氧六环为溶剂，在碳酸铯存在的条件下与缺电子炔烃经1，3-偶极环加成和芳构化反应即可得到3-芳基中氮茚，产率34%～81%. 该方法具有原料易得、操作简便、反应条件温和、选择性好等优点.

关键词: 中氮茚, 1,3-偶极环加成, 缺电子炔烃

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

引用此文

李国栋, 胡华友, 阚玉和, 马奎蓉. 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[J]. 有机化学, 2014, 34(5): 903-908.

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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