Aza-annulation of enaminones with crotonyl chloride - Formal reversal of regioselectivity.

被引：13

作者：

Murphy, JP ^{[1
]}

Hadden, M ^{[1
]}

Stevenson, PJ ^{[1
]}

机构：

[1] QUEENS UNIV BELFAST,SCH CHEM,BELFAST BT9 5AG,ANTRIM,NORTH IRELAND

来源：

TETRAHEDRON | 1997年 / 53卷 / 34期

关键词：

D O I：

10.1016/S0040-4020(97)00755-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regiochemistry of aza-annulation of enaminones with alpha,beta-unsaturated acid chlorides bearing hydrogen atoms on the gamma-carbon is reversed when triethylamine is used as mediator. When the reaction was carried out at lower temperatures as 3-acyl beta,gamma-unsaturated compound could be isolated which cyclised to the desired product under thermal or basic conditions. The nature of this intermediate strongly suggests that a vinyl ketene is the active acylating agent. (C) 1997 Elsevier Science Ltd.

引用

页码：11827 / 11834

页数：8

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