An efficient approach to access 2,5-disubstituted 1,3,4-oxadiazoles by oxidation of 2-arenoxybenzaldehyde N-acyl hydrazones with molecular iodine

BAŞPINAR KÜÇÜK H., Alhonaish A., YILDIZ T., GÜZEL M.

ChemistrySelect, vol.7, no.26, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 7 Issue: 26
  • Publication Date: 2022
  • Doi Number: 10.1002/slct.202201391
  • Journal Name: ChemistrySelect
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Keywords: N-acylhydrazones, oxidative cyclization, 1, 3, 4-oxadiazoles, molecular iodine
  • Istanbul Medipol University Affiliated: Yes

Abstract

An oxidative cyclization of 2-arenoxybenzaldehyde N-acyl hydrazones 3 a–o was employed to synthesize new 2,5-disubstituted 1,3,4-oxadiazole compounds 4 a–d, 4 f–i, 4 k–n. This method involves oxidative cyclization of 2-arenoxybenzaldehyde N-acyl hydrazones 3 a–o with molecular iodine mediated catalysis in which potassium carbonate served as a base. Characterization of all the synthesized novel compounds involved, proton and carbon NMR, mass spectrometry, and CHN elemental analysis. The synthesis of novel 2,5-disubstituted 1,3,4-oxadiazoles may display potential to provide pharmacologically important heterocyclic compounds.