A SIMPLE APPROACH TO PYRIMIDINE AND QUINAZOLINE DERIVATIVES BY [4+2] CYCLOADDITION OF 1,3-DIAZADIENES AND ENAMINES

被引：12
作者：
BARLUENGA, J
TOMAS, M
BALLESTEROS, A
LOPEZ, LA
机构：
[1] Instituto Universitario de Química Organometálica Enrique Moles, Facultad de Química, Universidad de Oviedo
来源：
HETEROCYCLES | 1994年 / 37卷 / 02期
关键词：
D O I：
10.3987/COM-93-S123
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of 2-trimethylsilyloxy- (1) and 2-trimethylsilylthio-1,3-diazabutadienes (2) with enamines derived from aliphatic aldehydes leads regio-and stereoselectively to substituted tetrahydropyrimidin-2(1H)-ones (3) and thiones (4) in high yields. Extension of this cycloaddition to cyclic enamines, e.g. derived from cyclohexanone, leading to quinazoline derivatives (9-10) is also described. These heterocycles undergo hydrolysis and dehydration to 3,4-dihydropyrimidine (7-8) and 3,4,5,6,7,8-hexahydroquinazoline (11-12) derivatives.
引用
收藏
页码：1109 / 1120
页数：12
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