A novel one-pot synthesis of ferrocenyl-substituted 1,2,4-oxadiazoles

ZORA M., KIVRAK A., Kelgokmen Y.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.759, pp.67-73, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 759
  • Publication Date: 2014
  • Doi Number: 10.1016/j.jorganchem.2014.02.018
  • Journal Name: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.67-73
  • Keywords: 1,2,4-Oxadiazole, Amidoxime, Ferrocene, 3-Ferrocenylpropynal, Conjugate addition, Cyclization, SOLVENT-FREE CONDITIONS, RADICAL-STABILIZING ABILITY, TYROSINE KINASE ZAP-70, ACTIVITY IN-VITRO, MICROWAVE IRRADIATION, ANTIMALARIAL ACTIVITY, PARALLEL SYNTHESIS, 1,3-DIPOLAR CYCLOADDITION, BIOLOGICAL EVALUATION, EFFICIENT SYNTHESIS
  • Middle East Technical University Affiliated: Yes

Abstract

One-pot synthesis of 5-ferrocenyl-1,2,4-oxadiazoles via the reaction between 3-ferrocenylpropynal and amidoximes is described. 3-Ferrocenylpropynal reacts with a variety of amidoximes in the presence of KOH in refluxing dioxane to afford a broad range of 5-ferrocenyl-1,2,4-oxadiazole derivatives. The reaction first produces the corresponding conjugate addition product which, upon cyclization and rearrangement, yields the targeted 1,2,4-oxadiazole. The reaction appears to be general for a diversity of amidoximes and tolerates the presence of aryl groups with electron-withdrawing and electron-donating substituents. (C) 2014 Elsevier B.V. All rights reserved.