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Paper | Regular issue | Vol 36, No. 5, 1993, pp.987-993
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6247
A Novel Synthetic Route to Cyanophenothiazines. First Example of Smiles Rearrangement from Halogenobenzonitriles

Yvette Mettey and Jean-Michel Vierfond*

*Laboratoire de Chimie Organique,GREAM, Faculte de Pharmacie,BP 199, 34 rue du Jardin des Plantes, 86005 Poitiers Cedex, France


The reaction of halogenobenzonitriles with 2-aminobenzenethiol gave, by a Smiles rearrangement 2-mercaptocyanodiphenylamines which are cyclised to cyanophenothiazines via a disulfide intermediate. A mechanism is proposed.