Year 2005, Month 5 (Section Full Articles, Page 1233)
Reaction of aromatic aldehydes with β-dicarbonyl compounds
in a catalytic system: piperidinium acetate—1-butyl-3-methylimidazolium
tetraf luoroborate ionic liquid*
E. S. Putilova, N. A. Troitskii, and S. G. Zlotin*
Condensation of aromatic (heteroaromatic) aldehydes with 1,3-dicarbonyl compounds under the 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim][BF4]) ionic liquid—piperidinium acetate catalytic system (0.2 equiv. of each component) in the absence of a
solvent affords, depending on the structures of the reagents, 2-arylidene derivatives of methyl
acetoacetate and acetylacetone, diethyl 2,4-bis(trifluoroacetyl)-3-phenylpentanedioate, or dimethyl 2-aryl-4-hydroxy-6-oxocyclohexane-1,3-dicarboxylates. The reactions of the resulting
2-arylidene derivatives with O-methylisourea in the [Bmim][BF4] ionic liquid produced me-
thyl 2-methoxy-4-methyl-6-aryldihydropyrimidine-5-carboxylates and 1-(2-methoxy-4-methyl-6-phenyldihydropyrimidin-5-yl)ethanone (mixtures of 3,6- and 1,6-dihydro isomers),
which were transformed into the corresponding 3,4-dihydropyrimidin-2(1H )-one derivatives.
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