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 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 759
  • Publication Date: 2014
  • Doi Number: 10.1016/j.jorganchem.2014.02.018
  • Title of Journal : JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Page Numbers: pp.67-73

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.