Synthesis of polyfunctionally substituted pyrimidines and pyridines condensed with other heterocyclic systems

Treatment of benzoylacetonitrile with anisaldehyde afforded alpha- cyanochalcone [I], which on reaction with malononitrile yielded 2-amino-3,5-dicyano-4-[p-methoxyphenyl]-6-phenyl-4H-pyran [III]. Compound III underwent Michael reaction with aniline derivatives to give 3,5-dicyano-4-[p-methoxyphenyl]-6-phenyl-2-[p-substituted arylamino] pyridine derivatives Va-d. Reaction of III with hydroxylamine hydrochloride, acetic anhydride, malononitrile and benzoylisothiocyanate gave, respectively, compounds IX, X, XI and XIV