Alexey I. Ilovaisky

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.

Synthetic Strategies for Peroxide Ring Construction in Artemisinin

The present review summarizes publications on the artemisinin peroxide fragment synthesis from 1983 to 2016. The data are classified according to the structures of a precursor used in the key peroxidation step of artemisinin peroxide cycle synthesis. The first part of the review comprises the construction of artemisinin peroxide fragment in total syntheses, in which peroxide artemisinin ring resulted from reactions of unsaturated keto derivatives with singlet oxygen or ozone. In the second part, the methods of artemisinin synthesis based on transformations of dihydroartemisinic acid are highlighted.

Electrooxidative cleavage of C1C2 bonds in acenaphthylene and acenaphthenes

Abstract The electrooxidative cleavage of C 1 C 2 bonds in acenaphthylene ( 1 ), acenaphthene ( 6 ), 1-methoxy-( 7 ), 1,1-dimethoxy- ( 8 ), and 1,2-dimethoxyacenaphthene ( 2 ) resulting from anodic oxidation of these substrates in MeOH is described. The reaction of 1 involves the intermediate formation of 2 , and that of 6 and 7 the formation of intermediates 2 and 8 to give 1,8-naphthalenedicarbaldehyde bis(dimethyl acetal) ( 3 ), cyclic dimethyl acetal ( 4 ), and 1,1,3-trimethoxy- lH ,3 H -naphtho[1,8-cd]pyran ( 5 ) as major final products.

Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions

The biological activity of organic peroxides is usually associated with the antimalarial properties of artemisinin and its derivatives. However, the analysis of published data indicates that organic peroxides exhibit a variety of biological activity, which is still being given insufficient attention. In the present review, we deal with natural, semi-synthetic and synthetic peroxides exhibiting anthelmintic, antiprotozoal, fungicidal, antiviral and other activities that have not been described in detail earlier. The review is mainly concerned with the development of methods for the synthesis of biologically active natural peroxides, as well as its isolation from natural sources and the modification of natural peroxides. In addition, much attention is paid to the substantially cheaper biologically active synthetic peroxides. The present review summarizes 217 publications mainly from 2000 onwards.

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.

Electrochemical Cleavage of Benzylic Single and Double Carbon-Carbon Bonds

Electrochemical transformations of aromatic hydrocarbons, which are based on the cleavage of benzylic carbon-carbon π- and σ-bonds, were investigated. The study pursued the main goals: (1) to establish characteristics of the structural and electrochemical factors affecting the course of these type of reactions, (2) to estimate their scope and limitations; and (3) to carry out the methodological development of the reactions to make them a convenient and efficient tool of organic synthesis.