ALKYLATION OF PYRIDINE-3,5-DICARBOXAMIDE AND PYRIDINE-3,5-DICARBONITRILES BY RADICAL SUBSTITUTION

Structural modification of NAD(P) model compounds, N,N,N',N'-tetramethylpyridine-3,5-dicarboxamide (1), pyridine-3,5-dicarbonitrile (2), and 4-methylpyridine-3,5-dicarbonitrile (3), have been explored by the reaction with alkyl radicals such as the 1-adamantyl, tert-butyl, and isopropyl radicals. The alkyl substitutions of compounds 1, 2, and 3 with the 1-adamantyl and the tert-butyl radical gave both 2-mono and 2,6-disubstitution products, whereas the reaction of compound 2 with the isopropyl radical gave 2-mono 6c, 2,4-di 7c, 2,6-di 8c, and 2,4,6-trisubstitution 9c products.