Facile and general synthesis of quaternary 3-aminooxindoles

Org Lett. 2008 Jul 3;10(13):2905-8. doi: 10.1021/ol801028e. Epub 2008 Jun 6.

Abstract

A novel approach to the valuable quaternary 3-aminooxindole skeleton is reported on the basis of intramolecular arylation of enolates of substituted amino acids. The reaction tolerates dialkyl- and arylalkylamines as well as a range of carbon substituents (primary and secondary alkyl, aryl). The cyclization of N-indolyl-substituted substrates is accompanied by direct C-H arylation of the indole, leading to indolo-fused benzodiazepines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Oxindoles

Substances

  • Amines
  • Indoles
  • Oxindoles
  • 2-oxindole
  • indoline