DEARYLATION WITH AROMATIZATION ON CYCLOCONDENSATION OF 4-(DIMETHYLAMINO)BENZALDEHYDE, 2-PHENACYLAZAHETEROCYCLES, AND 1,3-[N,C]DINUCLEOPHILES
DOI:
https://doi.org/10.1007/6895Keywords:
aldehydes, anilines, benzimidazoles, benzothiazoles, imidazoles, pyrazoles, pyrazolo[3, 4-b]pyridines, pyrido[2, 3-d]pyrimidines, pyrimidines, quinolines, aromatization, dearylation, Hantzsch reaction, selectivityAbstract
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.How to Cite
Dzvinchuk, I. B. Chem. Heterocycl. Compd. 2009, 45, 85. [Khim. Geterotsikl. Soedin. 2009, 101.]
For this article in the English edition see DOI 10.1007/s10593-009-0230-x
