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

Ryzhkova, Yuliya E.; Kalashnikova, Varvara M.; Ryzhkov, Fedor V.; Elinson, Michail N.

doi:10.3390/M1640

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

¹

N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia

²

Higher Chemical College at the Russian Academy of Sciences, D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., 125047 Moscow, Russia

^*

Author to whom correspondence should be addressed.

Molbank 2023, 2023(2), M1640; https://doi.org/10.3390/M1640

Submission received: 20 April 2023 / Revised: 4 May 2023 / Accepted: 5 May 2023 / Published: 8 May 2023

(This article belongs to the Collection Heterocycle Reactions)

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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-2H-pyran-2-one; ((2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine

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Ryzhkova, Y.E.; Kalashnikova, V.M.; Ryzhkov, F.V.; Elinson, M.N. 5-(1-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione. Molbank 2023, 2023, M1640. https://doi.org/10.3390/M1640

AMA Style

Ryzhkova YE, Kalashnikova VM, Ryzhkov FV, Elinson MN. 5-(1-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione. Molbank. 2023; 2023(2):M1640. https://doi.org/10.3390/M1640

Chicago/Turabian Style

Ryzhkova, Yuliya E., Varvara M. Kalashnikova, Fedor V. Ryzhkov, and Michail N. Elinson. 2023. "5-(1-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione" Molbank 2023, no. 2: M1640. https://doi.org/10.3390/M1640

APA Style

Ryzhkova, Y. E., Kalashnikova, V. M., Ryzhkov, F. V., & Elinson, M. N. (2023). 5-(1-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione. Molbank, 2023(2), M1640. https://doi.org/10.3390/M1640

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

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