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

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.

Automated summary

Many nitrogen- and sulfur-containing heterocyclic compounds with biological activity have been discovered. This study focuses on the synthesis of benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles, an important class of heterocycles. A new synthetic protocol involving oxidation and subsequent C-H bond functionalization is reported, which provides a short reaction time and high yields.