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Paper | Regular issue | Vol 92, No. 10, 2016, pp.1810-1821
Published online, 12th September, 2016
DOI: 10.3987/COM-16-13530
Synthesis of 2-Alk(or Aryl)oxy- and 2-(Alkyl(or Aryl)sulfanyl)-4H-3,1-benzothiazine Derivatives Carrying a (Z)-Halomethylidene Substutuent at the 4-Position

Kazuhiro Kobayashi* and Takashi Nogi

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

Abstract

2-Alk(or aryl)oxy-4-(Z)-(halomethylidene)-4H-3,1-benzothiazines were synthesized by the reaction of 2-(2,2-dihaloethenyl)phenyl isothiocyanates with sodium alk(or aryl)oxides. Similar treatment of the 2-(2,2- dibromoethenyl)phenyl isothiocyanates with sodium thiolates gave the corresponding 2-(alkyl(or aryl)sulfanyl)-4-(Z)-(bromomethylidene)-4H-3,1- benzothiazines. The above 2-aryloxybenzothiazine derivative underwent clean conversion to 2-aryloxy-4-(Z)-[(arylsulfanyl)methylidene]-4H-3,1-benzothiazines on treatment with sodium arenethiolates. 2-(Arylsulfanyl)-4-(Z)- [(arylsulfanyl)methylidene]-4H-3,1-benzothiazines were also synthesized by the reaction of 2-(2,2-dibromoethenyl)phenyl isothiocyanates with two equivalents of sodium arenethiolates.