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

• Published in: Molecular diversity Vol. 14; no. 4; pp. 833 - 839
• Main Authors: Elinson, Michail N, Merkulova, Valentina M, Ilovaisky, Alexey I, Demchuk, Dmitry V, Belyakov, Pavel A, Nikishin, Gennady I
• Format: Journal Article
• Language: English
• Published: Dordrecht Dordrecht : Springer Netherlands 01.11.2010; Springer Netherlands; Springer Nature B.V
• Subjects: Biochemistry; Biomedical and Life Sciences; C-H acids; Catalysis; Chemical reactions; Chemical synthesis; Cyclization; Efficiency; Electricity; Electrocatalysis; Electrochemical Techniques - methods; Ethanol; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - chemistry; Hydroxyquinolines - chemistry; Indoles - chemical synthesis; Indoles - chemistry; Isatin; Isatin - chemistry; Life Sciences; Macromolecular Substances - chemical synthesis; Macromolecular Substances - chemistry; Models, Biological; Multicomponent reactions; Nitriles - chemistry; Organic Chemistry; Pharmacy; Polymer Sciences; Pyranoquinoline; Quinolones - chemistry; Short Communication; Spiro Compounds - chemical synthesis; Spiro Compounds - chemistry; Spirooxindole; Electrocatalysis; Spirooxindole; C–H acids; Pyranoquinoline; Multicomponent reactions; Isatin
• ISSN: 1381-1991; 1573-501X
• DOI: 10.1007/s11030-009-9207-z

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.