3-取代异吲哚啉-1-酮、噌啉和1,2,4-[ ]-苯并三嗪衍生物的制备

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

Department of Chemistry, American University of Beirut, Riad El Solh, 1107 2020Beirut, Lebanon.

Department of Chemistry, University of California, One Shields Avenue, Davis, California95616, United States.

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

Herein, we report a new approach to synthesize a series of 1,2,4-[]-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-[]-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.

在此，我们报道了一种从3-取代异吲哚啉-1-酮合成一系列1,2,4-[ ]-苯并三嗪和噌啉衍生物的新方法。所有报道的产物均通过经济的两步合成程序获得，产率适中至高。噌啉（a）和1,2,4-[ ]-苯并三嗪（b）是由相应的3-取代异吲哚啉-1-酮分子内环化生成的，而这些异吲哚啉-1-酮又是通过2-氰基苯甲醛与2-(2-硝基苯基)乙腈（a）或2-硝基苯胺衍生物（b）的加成反应制备的。本文还提出了这种转化的可能机理。