Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions

被引：32

作者：

Aelterman, W

De Kimpe, N

Tyvorskii, V

Kulinkovich, O

机构：

[1] Univ Ghent, Fac Agr & Appl Biol Sci, Dept Organ Chem, B-9000 Ghent, Belgium

[2] Belarusian State Univ, Dept Organ Chem, Minsk 220050, BELARUS

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 01期

关键词：

D O I：

10.1021/jo000724t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of 2,3-disubstituted pyrroles and pyridines:,is described. The reaction of 3-halo-1-azaallylic carbanions, regiospecifically generated from alpha -halogenated ketimines, with omega -iodoazides led to the regiospecific formation of omega -azido-alpha -haloketimines. Treatment of these functionalized imines with tin(II) chloride afforded halogenated five-and six-membered cylic imines, which were transformed under mild conditions into 2,3-disubstituted pyrroles and pyridines. The stereoselective reduction of 2,3-dialkyl-3-chloro-1-pyrrolines to afford cis-2,3-dialkyl-3-chloropyrrolidines is also reported.

引用

页码：53 / 58

页数：6

共 21 条

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