Synthesis of quinolines and 2H-dihydropyrroles by nucleophilic substitution at the nitrogen atom of oxime derivatives

被引：25

作者：

Kitamura, M ^{[1
]}

Yoshida, M ^{[1
]}

Kikuchi, T ^{[1
]}

Narasaka, K ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

SYNTHESIS-STUTTGART | 2003年 / 15期

关键词：

nucleophilic substitution; oxime derivatives; quinolines; tetrahydroquinolines; 2H-dihydropyrroles;

D O I：

10.1055/s-2003-42439

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isomerization of oxime derivatives was researched in detail to find out the methods for the syn-anti isomerization of O-substituted oximes. Based on these findings were developed simple methods for the preparation of aza-heterocycles from both stereoisomers of oximes. Quinolines were synthesized from beta-aryl ketone oximes by treatment with trifluoroacetic anhydride and 4-chloranil. gamma,delta-Unsaturated O-methoxyacetyloximes were transformed to 2H-dihydropyrroles by reaction with methoxy-acetic acid.

引用

页码：2415 / 2426

页数：12

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