Aliphatic Acylhydrazides as Effective Alkylating Agents for the Copper-Catalyzed Oxidative Cyclization of N-Arylacrylamides

Dedicated to Professor Guoqiang Lin on the occasion of his 80^th birthday.

Abstract

An unprecedented use of readily accessible aliphatic acylhydrazides as alkylating agents has been demonstrated in the copper-catalyzed tandem alkylation/cyclization of N-arylacrylamides. A range of aliphatic acylhydrazides smoothly participated in the oxidative 5-exo-trig cyclization of N-arylacrylamides with CuCO₃ as the catalyst and DTBP as the oxidant, delivering structurally diverse 3,3-dialkyloxindoles in moderate to good yields. This study paves the way for the synthetic applications of aliphatic acylhydrazides as alkyl radical precursors.

Key words

acylhydrazide - N-arylacrylamide - oxindole - alkylation - copper - oxidative cyclization

Publication History

Received: 10 February 2023

Accepted after revision: 10 March 2023

Accepted Manuscript online:
10 March 2023

Article published online:
13 April 2023

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