Versatile Cyclization of Aminoanilino Lactones: Access to Benzotriazoles and Condensed Benzodiazepin‐2‐thiones

Abstract

Furanone 3 and pyranone 4 were obtained by the reaction of o‐phenylene derivatives with tetronic acid 1 or pyrone 2, respectively. Under diazotization reaction, these two enaminone derivatives 3 and 4 cyclized rapidly with good yields to generate benzotriazoles 5. On the other hand, when enaminones 3 and 4 were allowed to react with carbondisulfide as electrophile, cyclization led to benzodiazepin‐2‐thiones 6 fused to dihydropyrone or tetronic acid moieties.

Keywords:

• benzodiazepin‐thione
• benzotriazoles
• enaminones

Acknowledgment

The authors gratefully acknowledge the Comité Mixte d'Evaluation et de Prospective de la Coopération Inter‐Universitaire Algéro‐Française (CMEP), the Ministère de l'Enseignement et de la Recherche Scientifique, and the French Ambassy at Algiers for financial support.