(N-Isocyanimino)Triphenylphosphorane as an Efficient Reagent for the Preparation of N-Benzyl-1-Phenyl-1-(5-Phenyl-1,3,4-Oxadiazol- 2-yl)Methanamine Derivatives via in-Situ Generation of Densely Functionalized Iminophosphoranes

Abstract

A novel isocyanide-based four-component reaction between (N-isocyanimino) triphenylphosphorane, benzyl amine, benzaldehyde derivatives, and various carboxylic acids efficiently provides N-benzyl-1-phenyl-1-(5-phenyl-1,3,4-oxadiazol-2-yl)methanamine derivatives in good yields without using any catalyst or activation. The reaction can be carried out as a simple one-pot protocol at room temperature.

[Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: NMR Spectra for 5i.]

GRAPHICAL ABSTRACT

Keywords:

• 1,3,4-Oxadiazole
• four-component reaction
• aza-wittig
• iminophosphorane
• heterocyclization

Acknowledgments

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