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Electrocatalytic multicomponent one‐pot approach to tetrahydro‐2′ H , 4 H ‐spiro[benzofuran‐2,5′‐pyrimidine] scaffold
Author(s) -
Elinson Michail N.,
Ryzhkova Yuliya E.,
Vereshchagin Anatoly N.,
Ryzhkov Fedor V.,
Egorov Mikhail P.
Publication year - 2021
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4274
Subject(s) - chemistry , benzofuran , aldose reductase , combinatorial chemistry , pyrimidine , sodium bromide , scaffold , stereochemistry , organic chemistry , sodium , enzyme , medicine , biomedical engineering
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(2 H )‐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 ,4 H ‐spiro[benzofuran‐2,5′‐pyrimidines] used in this approach are promising for the development of novel aldose reductase inhibitors.