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Communication | Regular issue | Vol 14, No. 5, 1980, pp.639-642
Published online, 1st January, 1970
DOI: 10.3987/R-1980-05-0639
Synthesis of Heterocyclic Compounds XIX. Preparation of 4,6-Diaryl-3,5-dicyano-2-pyridones

C. Seoane, J. L. Soto,* and M. P. Zamorano

*Departamento de Química Orgánica, Facultad de Química, Universidad Complutense de Madridas, Ciudad Universitaria, E-28040 Madrid, Spain


Reaction of cyanoacetamide with α-benzoylcinnamonitriles (I) leads to a new series of 4,6-diaryl-3,5-dicyano-2-pyridones (IV).
The initial Michael’s addition is followed by a cyclization to a 6-hydroxy-2-piperidone ring (II), whose acid dehydration gives rise to 3,4-dihydro-2-pyridones (III). The latter are easily aromatized to 4,6-diaryl-3,5-dicyano-2-pyridones (IV) by treatment with sodium nitrite in sulfuric acid.