A convenient synthesis of 3,3-dichloroazetidines, a new class of azetidines

被引：30
|
作者：
Aelterman, W
De Kimpe, N
Declercq, JP
机构：
[1] State Univ Ghent, FAc Agr & Appl Biol Sci, Dept Organ Chem, B-9000 Ghent, Belgium
[2] Univ Catholique Louvain, Chim Phys & Cristallog Lab, B-1348 Louvain, Belgium
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 01期
关键词：
D O I：
10.1021/jo970342w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short synthesis of appropriately substituted 3,3-dichloroazetidines, a virtually unknown class of azetidines, is described. The reaction of 3,3-dichloro-1-azaallylic carbanions, generated from N-(1-aryl-2,2-dichloroethylidene)amines, with aromatic aldehydes produced alpha,alpha-dichloro-beta-hydroxy imines that, upon treatment with mesyl chloride, were converted into the corresponding beta-(mesyloxy) imines. Reaction of these alpha,alpha-dichloro-beta-(mesyloxy) ketimines with potassium cyanide or sodium borohydride in methanol furnished a variety of 2-cyano- and 2-methoxy-3,3-dichloroazetidines in a stereoselective manner. Reduction of beta-(mesyloxy) imines with sodium cyanoborohydride followed cyclization with potassium carbonate in DMSO yielded 3,3-dichloroazetidines as well.
引用
收藏
页码：6 / 11
页数：6
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