Synthesis of a new 2,4,6(1Н,3Н,5Н)pyrimidinetrione derivatives

Condensation of 5-acetyl-2,4,6(1H,3H,5H)-pyrimidinetrione with 3-fluoro-, 4-fluoro-, 2-methoxy-3,5-dichlorobenzaldehydes and methyl (4-formyl-2-oxo-2H-chromen-7-yl)carbamate in 1-BuOH in the presence of piperidine and acetic acid by boiling for 4 hours gave the corresponding 5-[(E)-3-aryl-2-propenoyl]-2,4,6(1H,3H,5H)-pyrimidinetriones) and methyl N-2-oxo-4-[(E)-3-oxo-3-(2,4,6-trioxohexahydro-5-pyrimidinyl)-1-propenyl]-2H-chromen-7-ylcarbamate. Reaction of 3-methoxy-4-hydroxy-, 3,5-dimethoxy-4-hydroxy-benzaldehydes with 5-acetyl-2,4,6(1H,3H,5H)-pyrimidinetrione in dioxane in the presence of boron trifluorideetherate at room temperature completes after 48 hours with the formation of the corresponding chalcones. The corresponding imines and 5-arylidene derivatives were obtained by condensation of barbituric acid with alkyl C-nitroso phenylcarbamates in methanol and hydroxy-substituted benzaldehydes in water. The condensation of 5-[(4-hydroxy-3,5-dimethoxyphenyl)methylene]-2,4,6(1H,3H,5H)-pyrimidinetrione with aminoguanidine bicarbonate results in the formation of 7-hydrazinyl-5-(4-hydroxy-3,5-dimethoxyphenyl)pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione. Cyclocondensation of 2,4,6(1H,3H,5H)pyrimidinetrione with methyl N-{3-[(E)-3-(4-methoxyphenyl)-2-propenoyl]phenyl}carbamate in acetic acid in the presence of P₂O₅ yielded methyl { 3-[5-(4-methoxyphenyl)-2,4-dioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidin-7-yl]phenyl}carbamate.