Fedor V. Ryzhkov

Catalysis of Cascade and Multicomponent Reactions of Carbonyl Compounds and CH Acids by Electricity

This review is concerned with modern trends in the use of electrochemically induced chain reactions in cascade and multicomponent electroorganic synthesis. The review summarizes the data on the use of electrochemically induced chain reactions in cascade and multicomponent organic synthesis, which were published mainly in the last decade.

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.

Pot, atom and step-economic (PASE) synthesis of medicinally relevant spiro[oxindole-3,4′-pyrano[4,3-b]pyran] scaffold

Abstract Fast (3 min) pot, atom and step economics (PASE) potassium fluoride catalyzed multicomponent reaction of isatins, malononitrile and 4-hydroxy-6-methyl-2H-pyran-2-one results in efficient formation of substituted spirooxindole-3,4′-pyrano[4,3-b]pyrans in 92–96% yields. The developed ‘on-solvent’ approach to the substituted spirooxindole-3,4′-pyrano[4,3-b]pyrans – the pharmacologically perspective substances with known antiviral, antileishmanial, anticonvulsant and anti-HIV activities – is beneficial from the viewpoint of diversity-oriented large-scale processes and represents fast and environmentally benign synthetic concept for the multicomponent reactions strategy.

Stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7-dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1-carboxylates

Abstract A new stereoselective cascade reaction of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid by the action of bromine in the presence of a base into substituted (barbituric acid)-5-spirocyclopropanes is described. The yields are in the range of 60%–75%. Nuclear magnetic resonance (NMR) studies indicate that this cascade transformation results in the stereoselective formation of spiro products with trans-configuration of aryl and alkoxycarbonyl substituents in the cyclopropane ring. The products are a perspective class of compounds with prominent pharmacological and physiological activity.

Efficient and facile ‘on-solvent’ multicomponent synthesis of medicinally privileged pyrano[3,2-c]pyridine scaffold

The new type of ‘on-solvent’ multicomponent reaction was found: transformation of benzaldehydes, malononitrile and 4–hydroxy-6-methylpyridin-2(1H)-one in the presence of sodium acetate as catalyst in a small amount of ethanol results in formation of substituted 2-amino-7-methyl-5-oxo-4-phenyl-5,6-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles in excellent 92–99% yields. This novel ‘one-pot’ process opens an efficient and convenient way to functionalize pyrano[3,2-c]pyridine systems, which are promising compounds for different biomedical applications.