Electrocatalytic multicomponent one‐pot approach to tetrahydro‐2′<i>H</i>,<scp>4<i>H</i></scp>‐spiro[benzofuran‐2,5′‐pyrimidine] scaffold
Michaïl N. Elinson, Yuliya E. Ryzhkova, A. N. Vereshchagin, Fedor V. Ryzhkov, Mikhail P. Egorov
Abstract
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(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.