5-(1-(4-Hydroxy-6-methyl-2-oxo-2<i>H</i>-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1<i>H</i>,3<i>H</i>,5<i>H</i>)-trione

Abstract

Multicomponent reactions have been demonstrated as a promising tool for the creation of diverse molecular structures with enhanced efficiency, reduced waste, and a high atom economy. Arylglyoxal monohydrates with two different carbonyl groups are well known as worthwhile synthons in organic synthesis. 2-Pyrone and pyrimidine-2,4,6-trione are versatile building blocks for the synthesis of key intermediates in synthetic organic chemistry as well as in medicinal chemistry. A simple and efficient tandem Knoevenagel–Michael protocol for the synthesis of the previously unknown 5-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimet-hylpyrimidine-2,4,6(1H,3H,5H)-trione was elaborated. The suggested method is based on the multicomponent reaction of phenylglyoxal hydrate, 1,3-dimethylbarbituric acid, and 4-hydroxy-6-methyl-2H-pyran-2-one. The structure of the synthesized compound was proven by 1H, 13C-NMR, and IR spectroscopy, mass spectrometry, and elemental analysis. A procedure for predicting the possible types of its biological activity was carried out for the title compound.

Keywords

• multicomponent reaction
• tandem Knoevenagel–Michael process
• phenylglyoxal hydrate
• 1,3-dimethylbarbituric acid
• 4-hydroxy-6-methyl-2<i>H</i>-pyran-2-one
• ((2<i>H</i>-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine