1,6-Diamino-2-oxopyridine-3,5-dicarbonitrile Derivatives in the Mannich Reaction

Abstract: 1,6-Diamino-2-oxo-1,2,3,4-tetrahydropyridine-3,5-dicarbonitriles under the action of primary aliphatic amines and an excess of 37% formalin in ethanol were converted into 2,3,8,9-tetrahydro-6,10-methano[1,2,4]triazolo[1,5-a][1,5]diazocine-6,10(7H)-dicarbonitrile derivatives. At the same time, the Mannich reaction in the case of 1,6-diamino-4-aryl-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles proceeds ambiguously, and, depending on the conditions, gives either N-ethoxymethylation products or 1,2,4-triazolo[1,5-a]pyridine derivatives. In silico predictive analysis of the biological activity of new compounds was carried out. © 2021, Pleiades Publishing, Ltd.