On water noncatalytic tandem Knoevenagel–Michael reaction of aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones
Michaïl N. Elinson, A. N. Vereshchagin, Yuliya E. Anisina, Natalia A. Leonova, Mikhail P. Egorov
Abstract
Heating aldehydes, N,N’-dimethylbarbituric acid and cyclohexane-1,3-diones in water results in fast formation of Knoevenagel–Michael adducts in 82–98% yields. This multicomponent process opens facile, efficient and environmentally benign way to the new functionalized [(2-hydroxy-6-oxocyclohex-1-en-1-yl)(aryl)methyl]pyrimidine-2,4(1H,3H)-diones bearing both barbituric acid and cyclohexane-1,3-dionemoieties separated by arylmethylene spacer, which are promising compounds for biomedical applications including analeptics, anti-AIDS and anticancer remedies.
Topics & Concepts
ChemistryKnoevenagel condensationBarbituric acidMichael reactionCyclohexaneAdductOrganic chemistryPyrimidineTandemCascade reactionMedicinal chemistryStereochemistryCatalysisMaterials scienceComposite materialMulticomponent Synthesis of HeterocyclesSynthesis and biological activitySynthesis of heterocyclic compounds