The Reactions of Arylmethylidene(ethylidene)furanones with NNucleophiles

Anis’kova, T. V.; Kamneva, I. E.; Egorova, A. Yu.

doi:10.2174/1570178614666161118172349

Cited by 4 publications

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“…As a substrate, 3-arylmethylidenefuran-2(3 H )-ones have some advantages. They can be easily 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(3 H )-ones are substances which combine the properties of internal esters and α,β-unsaturated carbonyl compounds, and they are able to react with substances with mobile hydrogen atoms.…”

Section: Introductionmentioning

confidence: 99%

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

2017

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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.

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