Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[e]-Benzotriazine Derivatives
Fatat B El Dhaibi1, Ali Youssef1, James C Fettinger2
1Department of Chemistry, American University of Beirut, Riad El Solh, 1107 2020Beirut, Lebanon.
Abstract:
Herein, we report a new approach to synthesize a series of 1,2,4-[e]-benzotriazine and cinnoline derivatives from 3-substituted isoindolin-1-one. All the reported products are obtained through an economical two-step synthetic procedure resulting in fair-to-high yields. Cinnolines (a) and 1,2,4-[e]-benzotriazines (b) result from an intramolecular cyclization of the corresponding 3-substituted isoindolin-1-ones, which, in turn, are prepared by an addition reaction from 2-cyanobenzaldehyde and 2-(2-nitrophenyl) acetonitrile (a) or 2-nitroaniline derivatives (b). A proposed mechanism for this transformation is presented.
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