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Paper | Regular issue | Vol 41, No. 10, 1995, pp.2263-2269
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7171
Synthesis of 2-Substituted 2,3-Dihydro-1,4-benzothiazine-3-thiones via Iminophosphoranes

Masahiko Takahashi* and Masaru Ohba

*Department of Materials Science, Faculty of Engineering, Ibaraki University, Hitachi, Ibaraki 316, Japan

Abstract

2-(Substituted methylsulfanyl)anilines (5) were treated with triphenylphosphine dibromide to yield iminophosphoranes (6), whose aza-Wittig reaction with carbon disulfide gave 2-(substituted methylsulfanyl)phenyl isothiocyanates (8). Cyclization of 8 by strong bases afforded 2-substituted 2,3-dihydro-1,4-benzothiazine-3-thiones (10).