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.
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页码:4245 / 4249
页数:5
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