Directed lithiation of unprotected quinolinecarboxylic acids

被引：17
|
作者：
Rebstock, AS [1 ]
Mongin, F [1 ]
Trécourt, F [1 ]
Quéguiner, G [1 ]
机构：
[1] IRCOF, UMR 6014, Lab Chim Organ Fine & Heterocycl, F-76131 Mont St Aignan, France
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 05期
关键词：
lithiation; quinolines; carboxylic acids; neighbouring group effects;
D O I：
10.1016/S0040-4039(01)02265-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The lithium salts of quinoline-2-carboxylic acid and 4-methoxyquinoline-2-carboxylic acid undergo deprotonation at C3 when treated with LTMP in THF at -25 and 0degreesC, respectively. The lithium salts of quinoline-3- and 4-carboxylic acids Lire more prone to nucleophilic addition; nevertheless, they are deprotonated at C4 and C3, respectively, when treated with LTMP in THF at -50degreesC. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：767 / 769
页数：3
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