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Paper | Regular issue | Vol 32, No. 1, 1991, pp.107-126
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5641
Synthesis of Thieno[3,2-f]morphan, Thieno[4,3-f]morphan and 3-Thiamorphinan Derivatives

Masatoshi Ban, Yutaka Baba, Kenji Miura, Yasuaki Kondo, and Mikio Hori*

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

Thieno[3,2-f]morphans (4-7), (27) and (28) were prepared by cyclization of 2-thenyl-4-hydroxypiperidines (3) or 2-thenyltetrahydropyridine (26) with hydrobromic acid. Thieno[4,3-f]morphans (37) and (38) and 3-thiamorphinan (47) were similarly prepared. Some kinds of N-substituents were introduced to the thienomorphans (5-7), (29) and (39) and a 3-thiamorphinan (48). Analgesic activities of the N-substituted compounds were investigated.