Acetonitrile derivatives as carbonyl synthons. One-pot preparation of diheteroaryl ketones via a strategy of sequential SNAr substitution and oxidation

J Org Chem. 2004 Feb 20;69(4):1364-7. doi: 10.1021/jo030234b.

Abstract

The anion of 2-aryl acetonitrile derivatives reacted with a variety of heteroaryl chlorides or bromides in an S(N)Ar manifold to afford intermediate anions which were susceptible to oxidation. The addition of sodium peroxide and aqueous NH(4)OAc solution effected oxidation to afford aryl heteroaryl ketones in good yields. Aryl acetonitrile derivatives are thus umpolung-type synthons of the corresponding aryl carbonyl functionality.

MeSH terms

  • Aminoacetonitrile / chemistry*
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry*
  • Hydrocarbons, Halogenated / chemistry
  • Ketones / chemical synthesis
  • Ketones / chemistry*
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Heterocyclic Compounds
  • Hydrocarbons, Halogenated
  • Ketones
  • Aminoacetonitrile