确定 N-氰基-2-卤代苯甲酰胺向 3-亚氨基异吲哚啉-1-酮和 3-氨基异吲哚啉-1-酮的 5-外-消化歧化环化的阳极材料

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-05 DOI:10.1002/adsc.202401276

Xiao-Qing Xie, Zi-Qiong Li, Wei Zhou, Chaozhihui Cheng, Jiang Bai, Haixin Ding, Xian-Rong Song, Mu-Jia Luo, qiang xiao

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引用次数: 0

摘要

本文介绍了一种由芳基自由基促成的 N-氰基-2-卤代苯甲酰胺的电还原 5-外-消化环化反应，为合成各种 3-亚氨基异吲哚啉-1-酮提供了一条便捷的路线，产率为 30-75%。只需使用锌板而不是石墨棒阳极，电合成产物就能通过芳基自由基介导的 5-exo-dig 环化和随后的还原氢化反应转变为多种 3-亚氨基异吲哚啉-1-酮。此外，这种决定 5-exo-dig 环化分化的阳极材料具有电化学条件温和、基质范围广和官能团耐受性好的特点。

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Anode material determined divergent 5-exo-dig cyclization of N-cyano-2-halobenzamides toward 3-iminoisoindolin-1-ones and 3-aminoisoindolin-1-ones

Herein, an electroreductive aryl radical enabled 5-exo-dig cyclization of N-cyano-2-halobenzamides is presented, providing a convenient route for the synthesis of a variety of 3-iminoisoindolin-1-ones in 30–75% yields. Simply by employing zinc plate instead of graphite rod anode, the products of the electrosynthesis are switched to diverse 3-aminoisoindolin-1-ones through aryl-radical-mediated 5-exo-dig cyclization and subsequent reductive hydrogenation. Furthermore, this anode material determined divergent 5-exo-dig cyclization features mild electrochemical conditions, excellent substrate scopes, and good functional group tolerance.

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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.