A systematic study of reaction of heterocyclic enamines with electrophilic alkynes: A simple and efficient synthetic route to 2-pyridinone-fused heterocycles

被引：46

作者：

Wang, MX ^{[1
]}

Miao, WS

Cheng, Y

Huang, ZT

机构：

[1] Chinese Acad Sci, Inst Chem, Beijing 100080, Peoples R China

[2] Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China

来源：

TETRAHEDRON | 1999年 / 55卷 / 51期

关键词：

D O I：

10.1016/S0040-4020(99)00937-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The reaction of heterocyclic enamines with ethyl propiolate and diethyl acetylenedicarboxylate has been systematically studied. In contrast to their heterocyclic ketene aminal analogues, heterocyclic enamines reacted with electrophilic alkynes via the Michael addition pathway rather than the aza-ene reaction mechanism. In the presence of a strong base such as sodium ethoxide and sodium hydride, the resulting Michael addition products underwent cyclocondensation reaction readily to produce 2-pyridinone-fused heterocycles in good to excellent yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：14611 / 14622

页数：12

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