铜催化的 2-(烷基芳基)乙腈和胺的串联环化反应：获得 3-羟基异吲哚啉酮

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-01-07 DOI:10.1002/adsc.202400809

Jiatian Li , Lin Pan , Xiangwen Tan , Huanfeng Jiang , Wanqing Wu

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引用次数: 0

摘要

在此，我们介绍了一种通过铜催化 2-(炔芳基)乙腈和胺的串联环化反应合成 3-羟基异吲哚啉酮衍生物的方法。该反应与 2-(炔芳基)乙腈和含有各种官能团的伯烷基胺兼容，可提供相应的 3-羟基吲哚啉酮衍生物，收率在 44% 至 82% 之间（中等至良好收率）。初步的机理研究表明，该反应涉及苄基碳的氧化、酰胺的形成、炔烃的水合和分子内环化，从而生成各种 3-羟基异吲哚啉酮。通过克级合成、后期功能化和天然产物的后修饰，进一步证明了该策略的实用性。

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Copper‐Catalyzed Tandem Cyclization of 2‐(Alkynylaryl)Acetonitriles and Amines: Access to 3‐Hydroxyisoindolinones

Herein, we describe an approach to the synthesis of 3‐hydroxyisoindolinone derivatives via copper‐catalyzed tandem cyclization of 2‐(alkynylaryl)acetonitriles and amines. This reaction is compatible with 2‐(alkynylaryl)acetonitriles and primary alkyl amines containing various functional groups, providing the corresponding 3‐hydroxyindolinone derivatives with yields ranging from 44%–82%. Preliminary mechanistic studies suggest that the reaction involves oxidation of the benzylic carbon, amide formation, hydration of the alkyne and intramolecular cyclization to produce various 3‐hydroxyisoindolinones. The practicality of the strategy was further demonstrated by gram‐scale synthesis, late‐stage functionalizations, and the post modification of natural products.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.