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Report | Regular issue | Vol 14, No. 11, 1980, pp.1779-1784
Published online, 1st January, 1970
DOI: 10.3987/R-1980-11-1779
Cyclization of 2-(Γ-Bromoacetoacetamido)pyridine Derivatives: Formation of N-Aryl-Γ-lactam Derivatives

Katsumi Tabei,* Hideharu Ito, and Toyozo Takada

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

1-(2-Pyridyl)-4-hydroxy-2-pyrrolidone (7) was obtained from 2-(γ-bromoacetoacetamido)pyridine (1) through the reduction of the β-carbonyl group with NaBH4, protection of the hydroxyl group by tetrahydropyranyl group, cyclization of the ether to a γ-lactam by using DBU, and subsequent hydrolysis of the ether. According to the similar synthetic process, 1-phenyl-4-hydroxy-2-pyrrolidone (8a) and 1-(p-methoxyphenyl)-4-hydroxy-2-pyrrolidone (8b) were derived from the corresponding γ-bromoacetoacetanilide derivatives.