z-logo
Premium
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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here