Pd-catalyzed benzylic C-H amidation with benzyl alcohols in water: a strategy to construct quinazolinones

J Org Chem. 2012 Aug 17;77(16):7046-51. doi: 10.1021/jo301282n. Epub 2012 Aug 9.

Abstract

A novel method for the synthesis of 4-phenylquinazolinones via a palladium-catalyzed domino reaction of o-aminobenzamides with benzyl alcohols is developed. This protocol involves N-benzylation, benzylic C-H amidation, and dehydrogenation in water, which may play an important role in the smooth generation of the (η(3)-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzamides / chemistry*
  • Benzyl Alcohols / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Hydrogen / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Palladium / chemistry*
  • Quinazolinones / chemical synthesis*
  • Stereoisomerism
  • Water

Substances

  • Benzamides
  • Benzyl Alcohols
  • Quinazolinones
  • Water
  • Palladium
  • Carbon
  • Hydrogen