The Reaction of N-Isocyaniminotriphenylphosphorane With Biacetyl in the Presence of (E)-Cinnamic Acids: Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives via Intramolecular AZA-Wittig Reactions of in Situ Generated Iminophosphoranes

Abstract

Reaction of N-isocyaniminotriphenylphosphorane with biacetyl in the presence of (E)-cinnamic acids proceeds smoothly at room temperature and under neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives in high yields. The reaction proceeds smoothly and straightforward under mild conditions and no side reactions are observed.

GRAPHICAL ABSTRACT

Keywords:

• N-isocyaniminotriphenylphosphorane
• biacetyl
• (E)-cinnamic acid
• 1,3,4-oxadiazole
• aza-Wittig reaction

Acknowledgments

This research was supported by the “Iran National Science Foundation: INSF.”