4-difluoromethylated quinoline synthesis via intramolecular SN2′ reaction of α-trifluoromethylstyrenes bearing imine moieties

被引：21
|
作者：
Mori, T [1 ]
Ichikawa, J [1 ]
机构：
[1] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
来源：
CHEMISTRY LETTERS | 2004年 / 33卷 / 09期
关键词：
D O I：
10.1246/cl.2004.1206
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Intramolecular cyclization of o-methyleneamino-substituted alpha-trifluoromethylstyrenes is promoted by DBU and a catalytic amount of KCN to provide 4-(difluoromethyl)quinolines. The reaction proceeds via (i) the generation of carbon nucleophiles from the imine moieties, (ii) their intramolecular S(N)2' reaction with loss of a fluoride ion, and (iii) subsequent aromatization by alkene isomerization.
引用
收藏
页码：1206 / 1207
页数：2
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