An efficient stereoselective synthesis of 3-spirocyclopentene- and 3-spiropyrazole-2-oxindoles via 1,3-dipolar cycloaddition reaction

Chem Commun (Camb). 2010 Apr 28;46(16):2826-8. doi: 10.1039/b924066g. Epub 2010 Feb 25.

Abstract

The chemistry phosphorus and sulfur ylides have been exploited for a facile, short and efficient synthesis of 3-spirocyclopentene- and 3-spiropyrazole-2-oxindoles from E- and Z-isomers of bromo derivatives of Morita-Baylis-Hillman adducts of isatin with Ph(3)P/activated alkene/K(2)CO(3) and Me(2)S/DEAD/K(2)CO(3), respectively, via [3 + 2]-annulation strategy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis
  • Alkenes / chemistry*
  • Cyclization
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Oxindoles
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkenes
  • Indoles
  • Oxindoles
  • Pyrazoles
  • Spiro Compounds
  • 2-oxindole