A Domino Approach for the Synthesis of 4-Carboxamide Oxazolines from Azirines

Abstract

A regio- and diastereoselective ring-expansion reaction of N-acylaziridines is described for the synthesis of 4-carboxamide oxazolines using InCl₃. A domino Ugi–Joullié/ring-expansion reaction of arylphenylazirines, isocyanides, and carboxylic acids leads to the target products through the N-acylaziridine intermediates in the presence of the indium catalyst. The oxazolines were synthesized in moderate to excellent yields with high atom economy and high bond-forming efficiency under mild reaction conditions.

Key words

domino approach - 4-carboxamide oxazolines - azirines

Publication History

Received: 17 December 2020

Accepted after revision: 26 July 2021

Accepted Manuscript online:
26 July 2021

Article published online:
17 August 2021

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