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Short Paper | Regular issue | Vol 83, No. 1, 2011, pp.107-116
Published online, 6th December, 2010
DOI: 10.3987/COM-10-12073
An Experimental Study of Special Leaving Group Behavior in the Reaction of Arylidenebarbituric Acids with Carbon Nucleophiles

Mohammad A. Bigdeli, Enayatollah Sheikhhosseini,* Azizollah Habibi, and Saeed Balalaie

*Faculty of Chemistry, Tarbiat Moallem Uinversity, no. 49, Mofateh Ave. Tehran, Iran


The reaction of benzylidenebarbituric acid and 1,3-dimethylbenzylidenebarbituric acid with malononitrile as well as with dimedone in piperidine is investigated. In reaction with malononitrile, substituted pyridine-3,5-dicarbonitriles are obtained, while with dimedone, xanthenes and/or 6-hydroxy-5-((2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)(aryl)methyl)-1,3-dimethyl pyrimidine-2,4(1H,3H)-dione derivatives are isolated.