4.5 Article

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

Journal

MOLECULAR DIVERSITY
Volume 14, Issue 4, Pages 833-839

Publisher

SPRINGER
DOI: 10.1007/s11030-009-9207-z

Keywords

Electrocatalysis; Multicomponent reactions; Pyranoquinoline; Spirooxindole; Isatin; C-H acids

Funding

  1. Russian Foundation for Basic Research [09-03-00003a]
  2. Leading Science Schools of Russian Federation [5022.2006.3]

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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.

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