An improved synthesis of 1,2,4-oxadiazoles on solid support

Bioorg Med Chem Lett. 2001 Mar 26;11(6):753-5. doi: 10.1016/s0960-894x(01)00028-2.

Abstract

The use of tetra-N-butylammonium fluoride (TBAF) as a mild and efficient reagent for the cyclodehydration of O-acyl amidoximes has been extended to the synthesis of 1,2,4-oxadiazoles on solid support. Argopore MB-CHO resin (Argonaut Technologies) was reductively aminated and subsequently acylated with 4-cyanobenzoyl chloride. Conversion of the nitrile to the amidoxime and acylation with a range of acid chlorides in parallel followed by treatment with TBAF under ambient conditions afforded a library of 3,5-disubstituted 1,2,4-oxadiazoles.

MeSH terms

  • Chemistry, Pharmaceutical
  • Drug Design
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / chemistry
  • Quaternary Ammonium Compounds / chemistry*

Substances

  • Oxadiazoles
  • Quaternary Ammonium Compounds
  • tetrabutylammonium