Reaction of magnesiated bases on substituted pyridines:: deprotonation or 1,4-addition?

被引：16

作者：

Bonnet, V ^{[1
]}

Mongin, F ^{[1
]}

Trécourt, F ^{[1
]}

Quéguiner, G ^{[1
]}

机构：

[1] IRCOF, Lab Chim Organ Fine & Heterocycl, UMR 6014, F-76131 Mt St Aignan, France

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 24期

关键词：

D O I：

10.1039/b007270m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(tert-Butyl)pyridine-2-carboxamide (1), N-phenylpyridine-2-carboxamide (7) and 2,2-dimethyl-N-(2-pyridyl)propanamide (18) are readily deprotonated at C3 with a stoichiometric amount of (PrMgCl)-Mg-i or Bu2Mg in THF under reflux. Subsequent trapping with various electrophiles (deuterated water, aldehydes, iodine and dimethyl disulfide) gives 2,3-disubstituted pyridines carrying a useful carboxylic acid- or amino-derived function at C2. When N-(tert-butyl)pyridine-3-carboxamide (12) and 2,2-dimethyl-N-(3-pyridyl)propanamide (22) are subjected to the same reaction conditions, 1,4-addition to the pyridine ring occurs, giving 4-alkyl derivatives. Starting from N-(tert-butyl)pyridine-4-carboxamide (15), 1,2-addition and deprotonation reactions occur simultaneously.

引用

页码：4245 / 4249

页数：5

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