SYNTHESES D'HETEROCYCLES AZOTES ET SOUFRES VIA LES 5-ARYLIMINO-4-CHLORO-5H-1,2,3-DITHIAZOLES ISSUS DE LA CONDENSATION D'AMINES AROMATIQUES AVEC LE SEL D'APPEL
VALÉRIE THIÉRY, BESSON THIERRY* GROUPE DE CHIMIE ORGANIQUE, LABORATOIRE DE GÉNIE PROTÉIQUE ET CELLULAIRE, EA3169, U.F.R. SCIENCES FONDAMENTALES ET SCIENCES POUR L'INGÉNIEUR, BÂTIMENT MARIE CURIE, UNIVERSITÉ DE LA ROCHELLE, F-17042 LA ROCHELLE CEDEX 1, FRANCE. TEL.: 05 46 45 82 76; FAX:
Reaction of 4,5-dichloro-1,2,3-dithiazolium chloride 1 (Appel salt) with primary aromatic amines allows access to N-arylimino-1,2,3-dithiazoles 2 usually in high yield. These imines have proved to be very versatile synthetic intermediates in heterocyclic chemistry, undergoing a variety of reactions initiated by nucleophilic attack at different sites on the dithiazole ring (the driving force being the regeneration of the latent cyano group in the dithiazole ring). Exploring the chemistry of Appel salt, we demonstrate in this paper that the starting imines 2 can be easily converted into 2-cyano derivatives of benzoxazines, benzoxazepines, quinazolines, benzothiazines, indolines, benzothiazoles and iminoquinolines. The heterocyclic compounds described are interesting precursors of biologically active molecules.
