Studies in the Synthesis of 10 H-8-Bromo and 9-Methyl-1-Azaphenothiazine and Their 5-Oxide Derivatives via Smiles Rearrangement

Abstract

The condensation of zinc salt of 2-amino-4-bromo/3-methyl benzene
thiols and 2-chloro-3-nitropyridine yielded an amine and a sulfide. The
sulfide was acetylated with acetic anhydride. The acetylated sulfide
undergoes Smiles rearrangement in acetone and KOH (2.22 mole) to
give the title compound. The amine also gave the same compound when
treated with dimethyl sulfoxide and ethanolic potassium hydroxide. The
acetylated sulfide rearranges to 10-acetyl derivative of the title compound
when treated with one mole of potassium hydroxide in acetone.
Further, 5-oxide derivatives can be obtained by reacting the title compound
with hydrogen peroxide. The structures of all the compounds are
confirmed by their IR and mass spectral data and elemental analysis.