Dialkylaminoacetonitrile derivatives as amide synthons. A one-pot preparation of heteroaryl amides via a strategy of sequential SNAr substitution and oxidation

J Org Chem. 2004 Feb 20;69(4):1360-3. doi: 10.1021/jo030233j.

Abstract

Dialkylamino acetonitrile derivatives were utilized as alternative to cyanohydrin synthons for preparation of the corresponding heteroaryl dialkyl amides via a strategy of sequential base-mediated coupling and oxidation. The most advantageous oxidant, NiO(2)-H(2)O, can readily oxidize 2-substituted aminoacetonitriles to the corresponding amides under both basic and neutral conditions by forming cyanohydrins in situ.

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Aminoacetonitrile / chemistry*
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry*
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Amides
  • Heterocyclic Compounds
  • Aminoacetonitrile