Electrochemical synthesis of cyclopropanes

Elinson, Michaïl N.; Dorofeeva, Evgeniya O.; Vereshchagin, A. N.; Nikishin, G. I.

doi:10.1070/rcr4465

Cited by 45 publications

(11 citation statements)

References 57 publications

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“…The electrocatalytic processes with C-H acids are often carried out in an undivided electrolyzer with alkali metal halides as mediators. The electrocatalytic synthesis of functionally substituted cyclopropanes and related spirocyclopropanes is a special class of such electrocatalytic processes [16][17][18]. Electrocatalytic reactions of heterocyclic C-H acids [19] have also been intensively studied, as they afford the synthesis of different classes of heterocyclic compounds with a wide range of bioactivity [20].…”

Section: Introductionmentioning

confidence: 99%

Electrocatalytic multicomponent one‐pot approach to tetrahydro‐2′H,4H‐spiro[benzofuran‐2,5′‐pyrimidine] scaffold

Elinson

Ryzhkova

Vereshchagin

et al. 2021

Journal of Heterocyclic Chem

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The new electrocatalytic multicomponent transformation has been found: the electrolysis of arylaldehydes, N,N 0 -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 0 H,4H-spiro[benzofuran-2,5 0pyrimidines] used in this approach are promising for the development of novel aldose reductase inhibitors.

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Section: Introductionmentioning

confidence: 99%

Electrocatalytic multicomponent one‐pot approach to tetrahydro‐2′H,4H‐spiro[benzofuran‐2,5′‐pyrimidine] scaffold

Elinson

Ryzhkova

Vereshchagin

et al. 2021

Journal of Heterocyclic Chem

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“…The electrocatalytic processes with C-H acids are often carried out in an undivided electrolyzer with alkali metal halides as mediators. The electrocatalytic synthesis of functionally substituted cyclopropanes and related spirocyclopropanes is a special class of such electrocatalytic processes [14][15][16]. Electrocatalytic reactions of heterocyclic C-H acids [17] have also been intensively studied, as they afford the synthesis of different classes of heterocyclic compounds with a wide range of bioactivity [18].…”

Section: Introductionmentioning

confidence: 99%

Efficient Electrocatalytic Approach to Spiro[Furo[3,2-b]pyran-2,5′-pyrimidine] Scaffold as Inhibitor of Aldose Reductase

et al. 2021

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A continuously growing interest in convenient and ‘green’ reaction techniques encourages organic chemists to elaborate on new synthetic methodologies. Nowadays, organic electrochemistry is a new useful method with important synthetic and ecological advantages. The employment of an electrocatalytic methodology in cascade reactions is very promising because it provides the combination of the synthetic virtues of the cascade strategy with the ecological benefits and convenience of electrocatalytic procedures. In this research, a new type of the electrocatalytic cascade transformation was found: the electrochemical cyclization of 1,3-dimethyl-5-[[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](aryl)methyl]pyrimidine-2,4,6(1H,3H,5H)-triones was carried out in alcohols in an undivided cell in the presence of sodium halides with the selective formation of spiro[furo[3,2-b]pyran-2,5′-pyrimidines] in 59-95% yields. This new electrocatalytic process is a selective, facile, and efficient way to create spiro[furo[3,2-b]pyran-2,5′-pyrimidines], which are pharmacologically active heterocyclic systems with different biomedical applications. Spiro[furo[3,2-b]pyran-2,5′-pyrimidines] were found to occupy the binding pocket of aldose reductase and inhibit it. The values of the binding energy and Lead Finder’s Virtual Screening scoring function showed that the formation of protein–ligand complexes was favorable. The synthesized compounds are promising for the inhibition of aldose reductase. This makes them interesting for study in the treatment of diabetes or similar diseases.

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“…The creation of easy and convenient methodology for the selective assembly of biologically active scaffolds in the electrocatalytic multicomponent processes becomes one of the principal goals of the modern electroorganic and green chemistry. [27][28][29] Among the different strategies of the drug discovery search, the identification and use of "privileged structures" or scaffolds gained a special attention in the last decades. 30 Usually, these privileged scaffolds are constructed from heterocyclic ring with specially determined positions of functional groups for target recognition of specified biological receptors.…”

Section: Introductionmentioning

confidence: 99%

Electrochemically induced tandem Knoevenagel-Michael assembling of aldehydes with kojic acid: direct and efficient arylbis[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl]methanes formation

Elinson¹,

Ryzhkova²,

Vereshchagin³

et al. 2020

Arkivoc

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The electrochemically induced tandem reaction of aldehydes and two equivalents of kojic acid has been carried out in alcohols in an undivided cell in the presence of sodium halides. It led to the selective formation of substituted arylbis[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl]methanes in 71-98% yields and with 240-330% current efficiency. This new electrocatalytic process provides green, useful and efficient way to two kojic acid fragments separated by C-aryl-substituted spacer, which are promising compounds for different biomedical applications.

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Electrochemical synthesis of cyclopropanes

Cited by 45 publications

References 57 publications

Electrocatalytic multicomponent one‐pot approach to tetrahydro‐2′H,4H‐spiro[benzofuran‐2,5′‐pyrimidine] scaffold

Electrocatalytic multicomponent one‐pot approach to tetrahydro‐2′H,4H‐spiro[benzofuran‐2,5′‐pyrimidine] scaffold

Efficient Electrocatalytic Approach to Spiro[Furo[3,2-b]pyran-2,5′-pyrimidine] Scaffold as Inhibitor of Aldose Reductase

Electrochemically induced tandem Knoevenagel-Michael assembling of aldehydes with kojic acid: direct and efficient arylbis[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl]methanes formation

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