Metal-free oxidative spirocyclization of hydroxymethylacrylamide with 1,3-dicarbonyl compounds: a new route to spirooxindoles

Org Lett. 2013 Oct 18;15(20):5254-7. doi: 10.1021/ol402473m. Epub 2013 Sep 27.

Abstract

A metal-free oxidative spirocyclization of hydroxymethylacrylamide with 1,3-dicarbonyl compounds is described. The reaction proceeds through tandem dual C-H functionalization and intramolecular dehydration, in which two new C-C bonds and one C-O bond were formed. This method affords a novel and straightforward access to various spirooxindoles under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylamides / chemistry*
  • Cyclization
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Ketones / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Oxidation-Reduction
  • Oxindoles
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry

Substances

  • Acrylamides
  • Indoles
  • Ketones
  • Oxindoles
  • Spiro Compounds
  • 2-oxindole