Unusual Oxidative Dimerization in the 3‑Aminothieno[2,3‑b]pyridine-2-carboxamide Series

Noncatalyzed, regio- and stereoselective hypochlorite oxidation of 3-aminothieno­[2,3-b]­pyridine-2-carboxamides is presented. Unexpectedly, the oxidation proceeded by different mechanistic pathways, and different products were formed, depending on the nature of solvents used. A possible mechanism, the structure of products, kinetics and dynamics of intramolecular processes, and biological activity of products are discussed.