Dearylation with aromatization on cyclocondensation of 4-(dimethyl-amino)benzaldehyde, 2-phenacylaza-heterocycles, and 1,3-[N,C]dinucleophiles

Three-component cyclocondensation involving p-(dimethylamino)benzaldehyde, 2-phenacylazahetero-cycle, and a 1,3-N,C]-nucleophile (3,5-dimethoxyaniline, 6-amino-1,3-dimethylpyrimidine-2,4-dione, 1-amino-3-methyl-5-phenylpyrazole) in boiling acetic acid is accompanied by aromatization of the initially formed annelated 4-(p-dimethylaminophenyl)-3-hetaryl-2-phenyl-1,4-dihydropyridines, the direction of which, with splitting off the dimethylaminophenyl substituent or its retention, is determined by the basicity of the hetaryl residue and the structure of the second ring, constructed on the binucleophile. A possible reaction mechanism is discussed. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 101-109, January, 2009.