Collect. Czech. Chem. Commun. 1984, 49, 2620-2627

Reaction of 3,5-dicyano-2,4,4,6-tetramethyl-1,4-dihydropyridine with nitric acid

Antonín Kurfürst and Josef Kuthan

Department of Organic Chemistry, Institute of Chemical Technology, 166 28 Prague 6


Reaction of the title compound I with nitric acid in acetic afforded a mixture of products which on column chromatography afforded 5-cyano-4,4,6-trimethyl-2-nitromethylene-3-oxo-1,2,3,4-tetrahydropyridine (II), (Z)-5-(1-acetoxy-2-nitrovinyl)-3,5-dicyano-4,4-dimethyl-2-pyrazoline (III) and 3-acetoxy-3-cyano-4,4,6-trimethyl-5-oxo-2,3,4,5-tetrahydropyridazine (IV). Reaction of I with nitrating mixture in chloroform gave only the compound II. The probable mechanism of formation of compounds II, III and IV, together with their 1H NMR, 13C NMR, IR and mass spectra, is discussed.