4.6 Article

The electrocatalytic cascade assembling of isatins, malononitrile and N-alkyl barbiturates:: An efficient multicomponent approach to the spiro[indole-3,5′-pyrano[2,3-d]pyrimidine] framework

Journal

ELECTROCHIMICA ACTA
Volume 53, Issue 28, Pages 8346-8350

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.electacta.2008.06.044

Keywords

electrolysis; electrocatalysis; spiroheterocycles; multicomponent reactions; cyclization; spiro[indole-3,5'-pyrano[2,3-d]pyrimidines]

Funding

  1. Russian Foundation [06-03-32181a]
  2. Presidential Scholarship Program [5022.2006.3]

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Electrochemically induced catalytic multicomponent transformation of isatins, barbituric acid or N-alkyl barbiturates and malononitrile in alcohols in an undivided cell results in the formation of substituted 7'-amino-2,2'.4'-trioxo-1,1',2,2',3'.4'-hexahydrospirolindole-3.5'-pyrano[2.3-d]pyrimidine]-6'-carbonitriles in 80-95% yields. The developed efficient electrocaralytic approach to corresponding spiro[indole-3,5'-pyratio[2,3-d]pyrimidine] system is beneficial from the viewpoint of diversity-oriented large-scale processes and represents a new example of the ecologically pure synthetic concept for electrocatalytic multicomponent reactions strategy. (c) 2008 Elsevier Ltd. All rights reserved.

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