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

Dong Xie; Ren-Gui Tian; Jia-Jia Liao; Shi-Kai Tian

doi:10.1055/a-2052-3331

Synthesis, Table of Contents

Synthesis 2023; 55(14): 2219-2227
DOI: 10.1055/a-2052-3331

paper

Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry

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

Dong Xie

,

Ren-Gui Tian

,

Jia-Jia Liao

,

Shi-Kai Tian∗

Abstract

All articles of this category

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

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