104416-16-2Relevant academic research and scientific papers
SYNTHESIS OF 3,5-DICYANO-4-PHENYL-2,6-BIS(4-p-TERPHENYLYL)-1,4-DIHYDROPYRIDINE. AN ATTEMPT AT EXTENDING THE HANTZSCH SYNTHESIS
Marchalin, Stefan,Kuthan, Josef
, p. 1962 - 1970 (2007/10/02)
The 3-oxopropanenitrile IIIc, prepared from 4-acetyl-p-terphenyl (IV) by the sequence IV -> V -> VI -> IIIc, reacts with benzaldehyde and ammonium acetate in acetic acid to give the Hantzsch dihydropyridine VIIc and the corresponding pyridine derivative VIIIc.The alternative cyclocondensation of benzylidene derivative IIc and 3-oxopropanenitrile IIIc in the presence of ammonium acetate exclusively gives the pyridine derivative VIIIc.Rate of thermal and oxidative aromatizations of the 1,4-dihydropyridine derivatives, VIIa-VIIc -> VIIIa-VIIIc, decreases in the order VIIc > VIIb > VIIa.Mechanism of these transformations and spectral characteristics of compounds VIIc and VIIIc are discussed with regard to their molecular structure.
