Valentina M. Merkulova

Electrochemically induced multicomponent assembling of isatins, 4-hydroxyquinolin-2(1H)-one and malononitrile: a convenient and efficient way to functionalized spirocyclic [indole-3,4′-pyrano[3,2-c]quinoline] scaffold

Electrochemically induced catalytic multicomponent transformation of isatins, 4-hydroxyquinolin-2(1H)-one and malononitrile in ethanol in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of spirooxindoles with fused functionalized indole-3,4′-pyrano[3,2-c]quinoline] scaffold in 75–91% substance yields and 500-600% current yield. The developed efficient electrocatalytic approach to medicinally relevant [indole-3,4′-pyrano[3,2-c]quinoline] scaffold is beneficial from the viewpoint of diversity-oriented large-scale processes and represents a novel example of facile environmentally benign synthetic concept for electrocatalytic multicomponent reactions.

Solvent-free multicomponent assembling of aldehydes, N,N′-dialkyl barbiturates and malononitrile: fast and efficient approach to pyrano[2,3-d]pyrimidines

Abstract Potassium fluoride-catalyzed solvent-free multicomponent reaction of aldehydes, N,N′-dialkyl barbiturates and malononitrile results in the fast (15 min) and efficient (yields 89–95%) formation of substituted pyrano[2,3-d]pyrimidines. The improved synthetic methodology for this class of bioactive compounds is important from the viewpoint of diversity-oriented large-scale processes and represents an environmentally benign solvent-free synthetic concept for multicomponent reactions strategy.

Electrosynthesis of esters of mono- and dioxoalkanoic and alkanedioic acids on the basis of nitro-substituted alkyl carboxylates and cycloalkanones

A one-pot electrochemical method for the synthesis of methyl monooxoalkanoates with the carbonyl group in position 4, methyl dioxoalkanoates with the oxo groups in positions 4,7-, 6,9-, 7,10-, and 12,15, and methyl 4-oxoalkanedioates was developed. This method is based on amperostatic electrolysis in an undivided cell of the salts of esters of nitroalkaniic acids and their adducts with CH2=CHX (X = Ac, CO2Me).

Electrochemical synthesis of geminal azidonitro compounds

An electrochemical method for the synthesis of geminal azidonitro compounds was developed. The method involves electrooxidative coupling of azide anions with salts of nitro compounds and affords geminal azidonitroalkanes, azidonitrocycloalkanes, and diazidodinitrocycloalkanes in 45–92% yields.

Electrooxidative transformation of unsubstituted and substituted nitro hydrocarbons into carbonyl compounds

Alkaline salts of aci-forms of secondary nitro compounds, viz., β-nitropropylbenzene, nitrocyclohexane, 5-nitroheptan-2-one, and methyl-4-nitrohexanoate, were selectively or predominately oxidized into the corresponding ketones and their ketals under conditions of undivided amperostatic electrolysis in methanol. Mixtures of the corresponding aldehydes, their acetals, and methyl carboxylates were formed under similar conditions from the salts of primary nitro compounds, viz., 1-nitrohexane, nitromethylbenzene, and β-nitroethylbenzene.

Silica gel mediated oxidative C–O coupling of β-dicarbonyl compounds with malonyl peroxides in solvent-free conditions

Abstract For the first time silica gel was observed to activate peroxides in oxidative coupling reactions. Here we report silica gel mediated oxidative C–O coupling of β-dicarbonyl compounds with cyclic diacyl peroxides affording α-acyloxy derivatives with 100% atom efficiency. The highest yields of coupling products were achieved in solvent free conditions. C–O coupling products were prepared in yields up to 86%.

Electrolysis of Nitro Compound Salts: Application in Ketone Synthesis

One-pot electrochemical method of synthesis of ketones, diketones, and esters of monoketo- and diketoalkanoic acids is elaborated. This method is based on the diaphragmless galvanostatic electrolysis of Na salts of secondary nitro compounds—derivatives of nitrohydrocarbons, nitroketones, and esters of nitrated alkanoic acids—in methanol.