Novel [4+2] cycloaddition reaction of arylmethylidenemalononitriles to unsaturated chalcogen amides. synthesis, structure, and properties of triethylammonium 3,5,5-tricyano1,4,5,6-tetrahydropyridine-2-selenolates and -thiolates

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2013-12, Vol.49 (9), p.1289
• Main Authors: Frolov, K.A, Dotsenko, V.V, Krivokolysko, S.G, Kostyrko, E.O
• Format: Article
• Language: English
• Subjects: Amides; Chemical properties; Heterocyclic compounds; Olefins
• ISSN: 0009-3122

Reaction of arylmethylidenemalononitriles with 3-aryl-2-cyanoprop-2-eneselenoamides in the presence of [Et.sub.3]N gave triethylammonium 4,6-diaryl-3,5,5-tricyano-1,4,5,6-tetrahydropyridine-2-selenolates. A similar reaction with cyclohexylidenecyanothioacetamide yields triethylammonium 4-aryl-1,5,5-tricyano-3- azaspiro[5.5]undec-1-ene-2-thiolate. Alkylation of the obtained selenolates and thiolates gives 6-(alkylseleno)-2,4-diaryl-1,4-dihydropyridine-3,3,5(2H)-tricarbonitriles and 4-(alkylthio)-2-aryl-3- azaspiro[5.5]undec-4-ene-1,1,5-tricarbonitriles, respectivelly. The structure of 2,4-di(2-furyl)-6-{[2-(4-methylphenyl)-2-oxoethyl]seleno}-1,4-dihydropyridine- 3,3,5(2H)-tricarbonitrile has been confirmed by the X-ray structural analysis. Keywords: arylmethylidenemalononitriles, cyanoselenoacetamide, cyanothioacetamide, prop-2-eneselenoamides, prop-2-enethioamides, 1,4,5,6-tetrahydropyridines, [4+2] cycloaddition, X-ray structural analysis.