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Paper | Regular issue | Vol 83, No. 9, 2011, pp.2127-2135
Published online, 21st July, 2011
DOI: 10.3987/COM-11-12283
Synthesis of 1,2,3,5-Tetrahydro-4,1-benzothiazepine-2-thione Derivatives via Cyclization of 2-[(2-Isothiocyanatophenyl)methylsulfanyl]acetates with Sodium Hydride

Kazuhiro Kobayashi,* Yoshinori Enmi, Daisuke Iitsuka, Yuuki Kanbe, and Hisatoshi Konishi

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan


A convenient method for the preparation of the title derivatives, 2-thioxo-1,2,3,5-tetrahydro-4,1-benzothiazepine-3-carboxylates and 2-alkylsulfanyl-3,5-dihydro-4,1-benzothiazepine-3-carboxylates, has been developed. It is depends on cyclization of 2-[(2-isothiocyanatophenyl)methylsulfanyl]acetates, generated in situ from the corresponding isocyanides on treatment with sulfur in the presence of a catalytic amount of selenium, using sodium hydride as a base. These isocyanides can be easily prepared from N-[(2-chloromethyl)phenyl]formamides via an easy two-step sequence.