Copper-catalyzed synthesis of isoindigoes and isatins from diazo(nitro)acetanilides

IF 1.4 4区化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR

Phosphorus, Sulfur, and Silicon and the Related Elements Pub Date : 2025-07-03 DOI:10.1080/10426507.2025.2515872

Xuan Ke (Data curation Formal analysis Investigation Methodology Validation Visualization Writing – original draft) , Chuangchuang Xu (Data curation Formal analysis Investigation Methodology) , Jiaxi Xu (Conceptualization Data curation Funding acquisition Investigation Methodology Resources Supervision Validation Visualization Writing – original draft Writing – review & editing)

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引用次数: 0

Abstract

N-Alkyldiazo(nitro)acetanilides generate both isoindigoes and isatins under the catalysis of Cu(MeCN)₄PF₆ in most cases and show obvious steric effect of both N-alkyl groups and substituents on anilines. Diazo(nitro)acetanilides with less bulky substituents generally favor formation of isoindigoes, while although those with more steric substituents generally disfavor the generation of isoindigoes, the yields of the corresponding isatins do not increase. The copper-catalyzed reaction of N-alkyldiazonitroacetanilides exhibits different chemoselectivity from other diazoacetanilides with α-electron-withdrawing substituents. The reactions were performed under both thermal and photo irradiation conditions, showing similar results.

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铜催化重氮（硝基）乙酰苯胺合成异靛蓝和异靛素

n -烷基重偶氮（硝基）乙酰苯胺在Cu(MeCN)4PF6的催化作用下多数生成异靛蓝和异靛素，并在苯胺上表现出明显的n -烷基和取代基的立体效应。取代基较少的重氮（硝基）乙酰苯胺通常有利于异靛蓝的生成，而取代基较多的重氮（硝基）乙酰苯胺通常不利于异靛蓝的生成，但相应的异靛蓝的产率不增加。铜催化的n-烷基重氮硝基乙酰苯胺的化学选择性不同于其他具有α-吸电子取代基的重氮乙酰苯胺。在热和光照射条件下进行了反应，得到了相似的结果。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Phosphorus, Sulfur, and Silicon and the Related Elements 化学-无机化学与核化学

CiteScore

2.60

自引率

7.70%

发文量

103

审稿时长

2.1 months

期刊介绍： Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.