Synthesis of N-Substituted Quinazolino[1,4]benzodiazepine: A Facial Route to N-Benzylsclerotigenin

Naim H. Al-Said,* Zakariyya N. Ishtaiwi
Department of Applied Chemical Sciences, Jordan University of Science and Technology. P.O. Box 3030, Irbid 22110, Jordan. Fax: 962-2-7095014. E-mail:

Synthesis of N-benzylsclerotigenin was achieved in four steps. Initially, isatoic anhydride was allowed to react with benzylamine and chloroacetyl chloride, respectively. The generated dipeptide derivative was then cylized to [1,4]benzodiazepinedione. Acylation with o-nitrobenzoyl chloride furnished a labile [1,4]benzodiazepinedione derivative, which upon reduction afforded N-benzylsclerotigenin in high yield. This methodology can be adopted in combinatorial synthesis of N-substituted quinazolino[1,4]benzodiazepindione library for biological evaluation. 

Key words: quinazolino[1,4]benzodiazepine, anthranilic ring system, N-benzylsclerotigenin, naturally occurring ring system