5--trione

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 synthesi...

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Bibliographic Details
Published in:MolBank 2023-05, Vol.2023 (2)
Main Authors: Ryzhkova, Yuliya E, Kalashnikova, Varvara M, Ryzhkov, Fedor V, Elinson, Michail N
Format: Article
Language:English
Subjects:
Analysis
Chemical synthesis
Identification and classification
Infrared spectroscopy
Mass spectrometry
Methods
Nuclear magnetic resonance spectroscopy
Pyrimidines
Structure
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Summary: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 [sup.1] H, [sup.13] C-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.
ISSN:1422-8599
1422-8599
DOI:10.3390/M1640