A facile solid-phase synthesis of 1,2,4,5-tetrasubstituted imidazoles using sodium benzenesulfinate as a traceless linker

J Comb Chem. 2005 Sep-Oct;7(5):644-7. doi: 10.1021/cc049818x.

Abstract

The preparation of substituted imidazoles, thiazoles, and oxazoles using traceless solid-phase sulfone linker strategy is described. Key steps involved are (i) sulfinate acidification, (ii) sulfinic acid condensation with aldehyde and amine, and (iii) traceless product release by a one-pot elimination-cyclization reaction. The elimination reaction was carried out in the presence of a thiazolium catalyst that facilitated the in situ formation of the alpha-ketoamide, which was subsequently converted to the corresponding imidazoles, oxazoles, and thiazoles by treatment with amines, PPh(3)/I(2) or Lawesson's reagent. A library of 18 compounds was synthesized.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques / methods*
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Oxazoles / chemical synthesis
  • Oxazoles / chemistry
  • Sodium / chemistry
  • Sulfinic Acids / chemistry*
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry

Substances

  • Imidazoles
  • Oxazoles
  • Sulfinic Acids
  • Thiazoles
  • benzenesulfinic acid
  • Sodium