Synthesis of 7-chloro-9-trifluoromethyl-/7-fluorophenothiazines

Abstract

Synthesis of 7-chloro-9-trifluoromethyl-/7-fluorophenothiazines is reported by Smiles rearrangement of 5-chloro-3-trifluoromethyl-/5-fluoro-2-formamido- 2′-nitrodiphenyl sulfides. The later were obtained by the formylation of 2-amino-5-chloro-7-trifluoromethyl-/5-fluoro-2′-nitrodiphenyl sulfides, which were prepared by the condensation of 2-amino-5-fluoro-/5-chloro-3- trifluoromethyl benzenethiols with o-halonitrobenzenes. 1-Nitrophenothiazines have also been synthesized by the condensation of 2-aminobenzenethiols with o-halonitrobenzenes, involving Smiles rearrangement in situ. © 2007 Wiley Periodicals, Inc.