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

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 α-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. © 2005 American Chemical Society.