A practical route to 2,3-di-/1,2,3-trisubstituted indolizines from α-EWG ketene S,S-acetals and their application in bis(1-indolizinyl)methane synthesis

被引：15

作者：

Sun, Shaoguang ^{[1
]}

Wang, Mang ^{[1
]}

Deng, Hongxia ^{[1
]}

Liu, Qun ^{[1
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2008年 / 04期

关键词：

indolizines; alpha-EWG ketene S; S-acetals; bis(1-indolizinyl)methanes; annulation; condensation;

D O I：

10.1055/s-2008-1032144

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easy synthesis of 2,3-di-/1,2,3-trisubstituted indolizines has been developed via a formal [3+2] annulation of alpha-EWG ketene S,S-acetals with 2-pyridine-/2-quinolinecarbaldehyde. The disubstituted products are formed via an intramolecular aza-Michael addition and subsequent elimination of acetic acid, followed by desulfenylation assisted by acetic acid, whereas the trisubstituted products are obtained via a similar conjugate addition followed by elimination of alkanethiol. This strategy has been applied to the synthesis of bis(1-indolizinyl)methanes by the condensation of a 2,3-disubstituted indolizine with aldehydes/ketones in the presence of a catalytic amount of BF(3)center dot OEt(2).

引用

页码：573 / 583

页数：11

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