Synthesis of N-Substituted Quinazolino[1,4]benzodiazepine: A Facial Route
to N-BenzylsclerotigeninNaim 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: naim@just.edu.jo
Abstract
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