Abstract: The new electrocatalytic multicomponent transformation has been found: the electrolysis of arylaldehydes, N,N′-dimethylbarbiturate, and cycloxehane-1,3-diones in alcohols in the presence of sodium bromide as a mediator in an undivided cell results in the formation of substituted unsymmetric spirobarbituric dihydrofurans in 62%–76% yields. The optimized reaction conditions and a mechanistic rationale for this electrocatalytic multicomponent transformation are presented. This new electrocatalytic process is a facile and efficient way to produce substituted unsymmetric spirobarbituric dihydrofurans containing both barbituric and 3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one fragments, which are promising compounds for different biomedical applications, among them are anticonvulsants, anti-AIDS agents, and antiinflammatory remedies. The scaffold approach was employed to find a protein, which may be influenced by the synthesized compounds—human aldose reductase was proposed. It was shown by molecular docking studies that such a scaffold search is beneficial and tetrahydro-2′H,4H-spiro[benzofuran-2,5′-pyrimidines] used in this approach are promising for the development of novel aldose reductase inhibitors.

Cite: Elinson M.N. , Ryzhkova Y.E. , Vereshchagin A.N. , Ryzhkov F.V. , Egorov M.P.
Electrocatalytic multicomponent one‐pot approach to tetrahydro‐2′H,4H‐spiro[benzofuran‐2,5′‐pyrimidine] scaffold
Journal of Heterocyclic Chemistry. 2021. V.58. N7. P.1484-1495. DOI: 10.1002/jhet.4274 WOS Scopus OpenAlex

Identifiers:

Web of science:	WOS:000644829900001
Scopus:	2-s2.0-85111793211
OpenAlex:	W3154929899

Citing:

DB	Citing
OpenAlex	8
Scopus	8
Web of science	9

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