Annulation of heterocyclic secondary enamines with dicarboxylic acid dichlorides, an unexpected ring size effect

被引:16
作者
Cheng, Y [1 ]
Yang, HB
Huang, ZT
Wang, MX
机构
[1] Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China
[2] Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0040-4039(00)02357-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under very mild conditions heterocyclic secondary enamines react efficiently with malonyl chloride to produce hydroxylated 2-pyridinone-fused heterocycles. The reactions of enamines with oxalyl chloride, however, afford varied products depending upon the heterocyclic structure of the enamine. Whilst a C-acylated enamine and a lactam-fused heterocycle were obtained from the reaction of the five- and seven-membered heterocyclic enamines, respectively, the six-membered heterocyclic enamine gave 2-oxo-5,6,7,8-tetrahydro-2H-pyrido[3,2-b]. The reaction mechanisms are discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1757 / 1759
页数:3
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