Evgenii V. Arshinov's research while affiliated with Omsk State University and other places

A new method was proposed for the synthesis of pyrido[3,4-c]cinnolines and pyrido[3,2-c]cinnolines. Pyridine-3-diazonium tetrafluoroborates, containing donor methoxy groups in one of the aryl substituents, form pyridocinnolines at 0°C by intramolecular azo coupling reaction. The 2´-methoxy group in the aryl substituent of the pyridine-3-diazonium salt participates in the aromatic nucleophilic substitution reaction, which results in the elimination of the diazo group to form benzofuro[2,3-c]pyridine and benzofuro[3,2-b]pyridine. The intermediate and target reaction products were isolated in high yields.

Interest in β-carbolines is caused by the biological activity of these compounds and the use of their fluorescent properties in the study of their interaction with DNA and other biological targets, as well as with drug delivery vehicles. A new general method for the synthesis of harmane, harmine, and their structural analogs by thermolysis of substituted 4-aryl-3-azidopyridines was developed, and their optical properties were studied.

3-Acetyl-4,6-diaryl-2-methylaminopyridines were synthesized via rearrangement of quaternary 4,6-diaryl-3-cyano-2-methylpyridinium salts. Annulation of the pyrazole ring of pyrazolo[3,4-b]pyridines was achieved by N-nitrosation of the methylamino group of the pyridine and reduction of N-nitroso group to the hydrazine group with simultaneous intramolecular closure of the pyrazole ring.