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Furan-derivatives .217. Synthesis and spectral properties of derivatives of 5-cyano-2-furaldehyde

D. Ilavský, S. Marchalín, J. Kováč, E. Henrybasch, and C. Morvan

Department of Organic Chemistry, Slovak Technical University, CS-812 37 Bratislava

Abstract: Knoevenagel condensation of 5-cyano-2-furaldehyde with propanedinitrile, amide of the cyanoacetic acid, methylcyanoacetate, 3-(2-furyl)-3-oxopropanenitrile, and 3-(4-methylphenyl)-3-oxopropanenitrile containing an active cyanomethylene group furnished the corresponding cyanoethylenes. Reaction of 5-cyano-2-furaldehyde with ethyl 3-oxobutanoate and 2,4-pentanedione gave ethyl 2-(5-cyano-2-furylidene)-3-oxobutanoate and 3-(5-cyano-2-furylidene)-2,4-pentanedione, respectively. Cyclocondensation of 5-cyano-2-furaldehyde with 3-amino-2-butenenitrile and 4-amino-3-pentene-2-one in the presence of ethanolic hydrogen chloride produced 4-(5-cyano-2-furyl)-2,6-dimethyl-l ,4-dihydropyridines. The structure-spectral properties relationship of the synthesized substituted 5-cyano-2--furylethylenes and 4-(5-cyano-2-furyl)-2,6-dimethyl-1,4-dihydropyridines is discussed.

Full paper in Portable Document Format: 416a793.pdf

Chemical Papers 41 (6) 793–802 (1987)