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.

Acid-catalyzed transformations of N-(5-methyl-2-furyl)ethyl 3-aminothieno[2,3-b]pyridine-2-carboxamides accompanied with furan ring opening were investigated. Based on furan ring recyclization several derivatives of the new fused heterocyclic system – pyrrolo[1,2-a][1,4]diazocine – were obtained. The structures of the synthesized compounds were assigned by their NMR, IR, and MS data.