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Communication | Regular issue | Vol 38, No. 8, 1994, pp.1733-1736
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6780
New Transformation of Lactam Sulfides to Tetrahydro-3,6-epithiobenzazocines via Bicyclic Sulfonium Salts with a Sulfonio Bridgehead

Tadashi Kataoka,*Yoshihide Nakamura, Harutoshi Matsumoto, Tetsuo Iwama, and Hiroshi Shimizu

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

Benzothiazinone (1) was chlorinated with N-chlorosuccinimide and subsequently submitted to [2++4] cycloaddition with 1,3-dienes in the presence of silver perchlorate to afford cyclic sulfonium salts (3). Reactions of 3 with sodium borohydride or sodium hydride provided 4-vinyltetrahydro-3,6-epithiobenzazocine derivatives (9) in good yields.