APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS .6. A GENERAL STUDY OF THE LITHIATION OF SECONDARY PICOLINE AMIDES AND ISONICOTINE AMIDES

被引：22
作者：
EPSZTAJN, J
JOZWIAK, A
CZECH, K
SZCZESNIAK, AK
机构：
[1] Department of Organic Chemistry, Institute of Chemistry, University of Łódź, Łódź
来源：
MONATSHEFTE FUR CHEMIE | 1990年 / 121卷 / 11期
关键词：
Benzoylation; Lithiated reactive intermediates - dual behaviour; Lithiation; Protonation; Secondary picoline- and isonicotine amides;
D O I：
10.1007/BF00808955
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The lithiation of secondary picoline- (1) and isonicotine-amides (2) and the subsequent reaction of the corresponding (N- and 3-)lithiated amides (3 and 4) with N,N-dimethylbenzamide towards the synthesis of the C3-benzoylated picoline (12 a) and isonicotine acids (13 a) has been investigated. The effect of the N-substituent upon the generation of the lithiated amides 3 and 4 has been studied. As a result it was found that the anilide function should be considered the best choice for direct metallation of the masked picoline- and isonicotinecarboxylic acids. The effects at various temperatures upon the generation of the lithiated reactive intermediates and the problems concerning their reactions with an acid (deuteriation) and an carbonyl electrophile are discussed. © 1990 Springer-Verlag.
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页码：909 / 921
页数：13
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