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■ Cyclization Reactions of 2-Methylbenzenesulfonamides Using N,N-Dimethylcarbamoyl Chloride, N,N-Dimethylthiocarbamoyl Chloride, and N,N-Dimethylsulfamoyl Chloride

Masahiko Takahashi,* Tomoya Morimoto, Ken-ichi Isogai, Sousi Tsuchiya, and Keisuke Mizumoto

*Department of Materials Sciences, Faculty of Engineering, Ibaraki University, 4-12-1 Nakanarusawamachi, Hitachi, Ibaraki 316-8511, Japan

Abstract

Generation of C,N-dianions (2) of 2-methylbenzenesulfonamides (1) followed by addition of N,N-dimethylcarbamoyl chloride gave 2-(N,N-dimethylcarbamoyl)-methylbenzenesulfonamides (3), which were cyclized to 3,4-dihydro-2H-1,2-benzo[e]thiazin-3-one 1,1-dioxides (5). 3-Dimethylamino-2H-1,2-benzo[e]thiazine 1,1-dioxides (7) were obtained in one step by the reaction of 2 with N,N-dimethylthiocarbamoyl chloride. On the other hand, the reaction of 2 with N,N-dimethylsulfamoyl chloride yielded 2,2’-ethylene-bis(benzenesulfonamide)s (10) and / or 2,3-dihydro-1,2-benzothiazole 1,1-dioxides (11).