Synthesis, spectroscopy and mutagenicity of novel heptenedinitriles

In this paper we report the isolation of an unexpected product from the condensation of α-methylcinnamaldehyde with arylacetonitriles using sodium ethoxide at room temperature, 2,6-Diaryl-4-methyl-5-phenyl-2-heptenedinitriles were obtained as a result of a 1,4 and 1,2-addition of the arylacetonitriles enolate at the carbon-carbon double bond and the carbonyl group of the α, β-Michael acceptors. The reaction products were identified on the basis of their infrared, proton and carbon-13 nuclear magnetic resonance spectral data as well as their elemental analyses. Three representative compounds were investigated concerning their mutagenic activity. Two of these compounds showed a weak mutagenicity while the third one showed a relatively stronger mutagenic action using Salmonella typhimurium strains TA97a and TA100.