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Short Paper | Regular issue | Vol 96, No. 11, 2018, pp.1999-2004
Published online, 5th November, 2018
DOI: 10.3987/COM-18-13995
Synthesis of 4H-1,3,2-Benzodithiazin-4-imine 1,1-Dioxide Derivatives by Oxidative Cyclization of 2-(Aminosulfonyl)benzothioamide Derivatives with Iodine

Kazuhiro Kobayashi* and Daiki Fujiwara

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

Abstract

An efficient method for the construction of the 4H-1,3,2-benzodithiazine structure utilizing facile experimental operations from readily available starting materials is described. 2-Substituted (Z)-N-alkyl-4H-1,3,2-benzodithiazin-4-imine 1,1-dioxides can be obtained by the treatment of 2-(aminosulfonyl)benzothioamides, derived from the reaction between 2,N-dilithio derivatives of secondary benzenesulfonamides and isothiocyanates, with iodine in the presence of two equivalents of triethylamine.