Synthesis of Compounds of the Pyrimidine Series Based on the Reactions of 3-Arylmethylidenefuran-2(3H)-ones with N,N-Binucleophilic Reagents.
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.
['Aniskova|Tatyana|T|', 'Grinev|Vyacheslav|V|', 'Yegorova|Alevtina|A|']
D066241:Carbon-13 Magnetic Resonance Spectroscopy D060326:Chemistry Techniques, Synthetic D005663:Furans D015394:Molecular Structure D066244:Proton Magnetic Resonance Spectroscopy D011743:Pyrimidines
heterocyclization biological active compounds 5-R-3-arylmethylidenefuran-2(3H)-ones binucleophilic reagents dihydrofuro[2,3-d]pyrimidines plant-growth regulators pyrimidine derivatives pyrimidinylmethylene-phenylfuran-2(3H)-ones