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 (2a–d). 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 (1e–h) with thiourea in the basic medium leads to the isolation of 5-(2-oxo-2-phenylethyl)-6-aryl-2-thioxotetrahydropyrimidine-4(1H)-ones (3a–d), demonstrating pronounced plant-growth regulatory activity. Optimal conditions for all discussed processes were developed.
Highlights
Heterocyclic compounds containing a pyrimidine fragment can be natural or synthetic analogues of nucleosides and nucleotides
(1e–h) with thiourea in the basic medium leads to the isolation of 5-(2-oxo-2-phenylethyl)6-aryl-2-thioxotetrahydropyrimidine-4(1H)-ones (3a–d), demonstrating pronounced plant-growth regulatory activity
3-arylmethylidenefuran-2(3H)-ones have obtained, and they are convenient, cost-effective substrates for the synthesis of various hard-to-reach obtained, and they are convenient, cost-effective substrates for the synthesis of various hard-to-reach heterocyclic, spirocyclic, and polycyclic compounds [15,16,17,18,19,20,21,22,23,24,25]. 3-Arylmethylidenefuran-2(3H)-ones are heterocyclic, spirocyclic, and polycyclic compounds [15,16,17,18,19,20,21,22,23,24,25]. 3-Arylmethylidenefuran-2(3H)-ones are substances which combine the properties of internal esters and α,β-unsaturated carbonyl the properties of internal esters and α,β-unsaturated carbonyl compounds, substances which whichcombine combine the properties of internal esters and α,β-unsaturated carbonyl compounds, and they are able to react with substances with mobile hydrogen atoms
Summary
Heterocyclic compounds containing a pyrimidine fragment can be natural or synthetic analogues of nucleosides and nucleotides. They are of considerable interest due to a variety of their biological activities. The pyrimidine structural moiety is responsible for many kinds of biological activity, and is found in the molecules of natural compounds (guanidine, folic acid, etc.) as well as synthetic drugs (antitumor, antiviral, antibacterial drugs, etc.) [1,2,3,4,5,6,7,8]. There are some approved, effective, well-known medicines containing pyrimidine moieties (Figure 1), such as antimicrobial agent Trimethoprim [9], antiparkinsonian agent Piribedil [10], and antiviral medication Aciclovir (Zovirax) [11], etc.
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