Synthesis of Novel Heterocyclic Compound: Isoindolinone, Cinnoline and Benzotriazine Derivatives

Abstract

Heterocyclic chemistry of organic compounds made an important progress in the last century. α-phentriazine, also known as benzo-fused analogs or 1,2,4-benzotriazine and cinnoline constitute an important class of the biological active compounds. Due to their wide range of applications in the biological, medicinal, pharmaceutical and therapeutic fields (acting as: anti-tumor, anti-inflammatory, anti-analgesic and anti-malarial drugs) as well as their electronic and photonic properties, and despite all the monumental effort made to enhance the synthesis of these novels, a robust, economic and green synthetic methodology that increase the yield and generate a bulk amount of the desired product is needed. Thus, we worked on developing and accessing an easy and time consumed process yielding our target products 1,2,4-benzotriazines and cinnoline. The aim of our project is to synthesize a series of 1,2,4-benzotriazine derivatives and cinnoline compounds via the intermediate solid isoindolinone. Indeed, 27 compounds (both the ester and acid products) were synthesized in two steps reactions each. Whereby, after each step, all the structures of the stated compounds were isolated as yellow solid products, and characterized by spectroscopic analysis: IR, 1H NMR, 13C NMR, DEPT.135, UV-visible and melting points. The molecular weight was determined by high resolution mass spectroscopy (HR-MS). Moreover, the X-ray structure of the product: methyl 2-(7-methoxybenzo[e][1,2,4]triazin-3-yl)benzoate was resolved by Dr. James Fettinger and Distinguished Professor Mark Kurth, from the Chemistry Department of the University of California, Davis CA, USA.