Synthesis of Benzo[4,5]thiazolo[2,3-<i>c</i>][1,2,4]triazole Derivatives via C-H Bond Functionalization of Disulfide Intermediates

Abstract

Many nitrogen- and sulfur-containing heterocyclic compounds exhibit biological activity. Among these heterocycles are benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles for which two main synthetic approaches exist. Here we report a new synthetic protocol that allows the preparation of these tricyclic compounds via the oxidation of a mercaptophenyl moiety to its corresponding disulfide. Subsequent C-H bond functionalization is thought to enable an intramolecular ring closure, thus forming the desired benzo[4,5]thiazolo[2,3-c][1,2,4]triazole. This method combines a high functional group tolerance with short reaction times and good to excellent yields.

Keywords

• heteroaromatics
• C-H bond functionalization
• oxidative cyclization