DEAD-Mediated Oxidative Ugi/Aza-Wittig Reaction for the Synthesis of 5-(1,2,3,4-Tetrahydroisoquinolin-1-yl)-1,3,4-oxadi­­azoles Starting from (N-Isocyanimine)triphenylphosphorane

Abstract

A one-pot protocol for the synthesis of 5-(1,2,3,4-tetra­hydroisoquinolin-1-yl)-1,3,4-oxadiazoles via DEAD-mediated oxidative Ugi/aza-Wittig reaction has been developed. The reaction of (N-iso­cyanimine)triphenylphosphorane, carboxylic acids, and N-aryl-1,2,3,4-tetrahydroisoquinolines produced polysubstituted 5-(1,2,3,4-tetra­hydroisoquinolin-1-yl)-1,3,4-oxadiazoles directly in good yields in the presence of DEAD as an oxidant.

Key words

oxidative Ugi reaction - aza-Wittig reaction - 1,3,4-oxadiazole - 1,2,3,4-tetrahydroisoquinoline - (N-isocyanimine)triphenylphosphorane

Publication History

Received: 09 September 2020

Accepted after revision: 08 October 2020

Article published online:
10 November 2020

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