Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[ e]-Benzotriazine Derivatives

Fatat B El Dhaibi; Ali Youssef; James C Fettinger; Mark J Kurth; Makhluf J Haddadin

doi:10.1021/acsomega.2c03045

Preparation of 3-Substituted Isoindolin-1-one, Cinnoline, and 1,2,4-[ e]-Benzotriazine Derivatives

ACS Omega. 2022 Jul 20;7(30):26871-26880. doi: 10.1021/acsomega.2c03045. eCollection 2022 Aug 2.

Authors

Fatat B El Dhaibi¹, Ali Youssef¹, James C Fettinger², Mark J Kurth², Makhluf J Haddadin¹

Affiliations

¹ Department of Chemistry, American University of Beirut, Riad El Solh, 1107 2020Beirut, Lebanon.
² Department of Chemistry, University of California, One Shields Avenue, Davis, California95616, United States.

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.