Masatoshi Ban

Syntheses of thieno[3,2-f]morphan, thieno[4,3-f]morphan and 3-thiamorphinan derivatives

Thieno[3,2-f]morphans (4-7), (27) and (28) were prepared by cyclization of 2-thenyl-4-hydropiperidines (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-sub and a 3-thiamorphinan (48). Analgesic activities of the N-substituted compounds were investigated

10-Thia-anthracenes. Part 3. A re-examination of the reaction of 9-phenylthioxanthylium salt and phenyl-lithium

Reaction of 9-phenylthioxanthylium salt (1) with phenyl-lithium afforded eight compounds, 9-phenyl(2), 9,9-diphenyl-(3), 3,9-diphenyl-(4), 3,9,9-triphenyl-(5), and 4,9,9-triphenyl-thioxanthene (6), 9,9′-diphenyl-9,9′-bithioxanthenyl (7), thioxanthone (8), and 9,9′-diphenyldithioxanth-9-yl peroxide (9). Their structures were determined by comparison with the authentic samples. Six samples, (3)–(6), 2,9,9-triphenyl-(30), 9-(biphenyl-4-yl)-9-phenylthioxanthene (31) were independently synthesized in order to determine the structures of two pairs of positional isomers, 3,4, and 5,6. A radical mechanism contributed to the reaction of compound (1) with phenyl-lithium.