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

Mol Divers. 2010 Nov;14(4):833-9. doi: 10.1007/s11030-009-9207-z. Epub 2009 Nov 17.

Abstract

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.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Efficiency
  • Electrochemical Techniques / methods*
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry
  • Hydroxyquinolines / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Isatin / chemistry*
  • Macromolecular Substances / chemical synthesis*
  • Macromolecular Substances / chemistry
  • Models, Biological
  • Nitriles / chemistry*
  • Quinolones / chemistry*
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry

Substances

  • Heterocyclic Compounds
  • Hydroxyquinolines
  • Indoles
  • Macromolecular Substances
  • Nitriles
  • Quinolones
  • Spiro Compounds
  • Isatin
  • dicyanmethane
  • 4-hydroxyquinoline