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Molecules 2017, 22(8), 1251; doi:10.3390/molecules22081251

Synthesis of Compounds of the Pyrimidine Series Based on the Reactions of 3-Arylmethylidenefuran-2(3H)-ones with N,N-Binucleophilic Reagents

1
Institute of Chemistry, Chernyshevsky Saratov State University, Ulitsa Astrakhanskaya 83, 410012 Saratov, Russia
2
Institute of Biochemistry and Physiology of Plants and Microorganisms RAS, Prospekt Entuziastov 13, 410049 Saratov, Russia
*
Author to whom correspondence should be addressed.
Received: 10 July 2017 / Revised: 25 July 2017 / Accepted: 25 July 2017 / Published: 28 July 2017
(This article belongs to the Special Issue Nucleoside and Nucleotide Analogues)
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Abstract

The arylmethylidene derivatives of furan-2(3H)-ones are important building blocks for the synthesis of various heterocyclic compounds containing pyrimidine and pyridazine structural fragments, analogues of nitrogen-containing bases of pyrimidine series. In order to continue the development of constructing of molecules containing pyridine and pyridazine fragments, this article is devoted to the synthesis of new biologically active compounds with these moieties. The introduction of a heterocyclic chromenone fragment changes the previously observed 5-R-3-arylmethylidenefuran-2(3H)-ones route of reaction with guanidine carbonate and leads to 3-[(2-amino-4-(2-hydroxyphenyl)pyrimidin-5-yl)methylene]-5-phenylfuran-2(3H)-ones (2ad). The structure of the reaction products depends on the nature of the aromatic substituent at the C-3 position of the furanone ring. The interaction of 5-aryl-3-arylmethylidenefuran-2(3H)-ones (1eh) with thiourea in the basic medium leads to the isolation of 5-(2-oxo-2-phenylethyl)-6-aryl-2-thioxotetrahydropyrimidine-4(1H)-ones (3ad), demonstrating pronounced plant-growth regulatory activity. Optimal conditions for all discussed processes were developed. View Full-Text
Keywords: pyrimidine derivatives; dihydrofuro[2,3-d]pyrimidines; pyrimidinylmethylene-phenylfuran-2(3H)-ones; biological active compounds; plant-growth regulators; 5-R-3-arylmethylidenefuran-2(3H)-ones; binucleophilic reagents; heterocyclization pyrimidine derivatives; dihydrofuro[2,3-d]pyrimidines; pyrimidinylmethylene-phenylfuran-2(3H)-ones; biological active compounds; plant-growth regulators; 5-R-3-arylmethylidenefuran-2(3H)-ones; binucleophilic reagents; heterocyclization
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Aniskova, T.; Grinev, V.; Yegorova, A. Synthesis of Compounds of the Pyrimidine Series Based on the Reactions of 3-Arylmethylidenefuran-2(3H)-ones with N,N-Binucleophilic Reagents. Molecules 2017, 22, 1251.

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