Reactions of 1, 4-bis (trimethylsilyl)-1, 4-dihydropyridines with carbonyl compounds: A new method for regioselective synthesis of 3-alkylpyridines.

…, S Kanemasa, T Naritomi, J Tanaka

Index: Tsuge, Otohiko; Kanemasa, Shuji; Naritomi, Toshio; Tanaka, Junji Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 4 p. 1497 - 1504

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Citation Number: 26

Abstract

A new method for the alkyl group introduction at the 3-position of pyridienes is described: Reductive disilylation of pyridine, its 2-methyl, 3-methyl, and 4-methyl derivatives affords the corresponding 1, 4-disilyl-1, 4-dihydropyridines. In the presence of a catalytic amount of tetrabutylammonium fluoride, these dihydropyridines smoothly react with a variety of aldehydes and ketones to give 3-alkylpyridines.