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

Tatyana A Stroganova; Vladimir K Vasilin; Victor V Dotsenko; Nicolai A Aksenov; Pavel G Morozov; Pavel M Vassiliev; Vitaly A Volynkin; Gennady D Krapivin

doi:10.1021/acsomega.1c00341

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

ACS Omega. 2021 May 28;6(22):14030-14048. doi: 10.1021/acsomega.1c00341. eCollection 2021 Jun 8.

Authors

Tatyana A Stroganova¹, Vladimir K Vasilin¹, Victor V Dotsenko^{2

3}, Nicolai A Aksenov³, Pavel G Morozov⁴, Pavel M Vassiliev⁵, Vitaly A Volynkin⁶, Gennady D Krapivin⁷

Affiliations

¹ Department of Bioorganic Chemistry, Kuban State Technological University, Krasnodar 350072, Russian Federation.
² Department of Organic Chemistry and Technologies, Kuban State University, Krasnodar 350040, Russian Federation.
³ Department of Organic Chemistry, North Caucasus Federal University, Stavropol 355009, Russian Federation.
⁴ Department of Chemistry of Natural Compounds, Southern Federal University, Rostov-on-Don 344006, Russian Federation.
⁵ Volgograd State Medical University, Volgograd 400131, Russian Federation.
⁶ Department of Inorganic Chemistry, Kuban State University, Krasnodar 350040, Russian Federation.
⁷ Scientific Research Institute of Chemistry of Heterocyclic Compounds, Kuban State Technological University, Krasnodar 350072, Russian Federation.

Abstract

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.