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■ Dimsylsodium-induces Rearrangement of Alkylimidates to N-Alkyllactams

Shinzo Kano,* Tsutomu Yokomatsu, Satoshi Hibino, Keiko Imamura, and Shiroshi Shibuya

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

Abstract

Treatment of 1-ethoxy-3,4-dihydro-6,7-dimethoxyisoquinoline (1) with dimsylsodium yielded 2-ethyl-1,2,3,4-tetrahydro-6,7-dimethoxy-1-oxoisoquinoline (2). Similarly, 2-ethoxy-4,5-dihydro-3H-pyrrole (3), 2-ethoxy-3,4,5,6-tetrahydropyridine (5), 7-ethoxy-3,4,5,6-tetrahydro-2H-azepine (7), and 7-ethoxy-3,4,5,6-tetrahydro-4-methyl-2H-azepine (9) were allowed to react with dimsylsodium to give the corresponding N-ethyllactams (4), (6), (8), and (10), respectively, through O to N migration of ethyl group by the catalytic action of dimsylsodium.