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Synthesis 2021; 53(07): 1365-1371
DOI: 10.1055/s-0040-1705967
DOI: 10.1055/s-0040-1705967
paper
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
We gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (No. 21572075) and the 111 Project B17019.
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)triphenylphosphoraneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705967.
- Supporting Information
Publication History
Received: 09 September 2020
Accepted after revision: 08 October 2020
Article published online:
10 November 2020
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