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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
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-11-06 , 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

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.

中文翻译:


负极材料确定了 N-氰基-2-卤代苯甲酰胺对 3-亚氨基异吲哚英-1-1-和 3-氨基异吲哚酯-1-酮的不同 5-exo-dig 环化



在此,提出了一种电还原芳基使 N-氰基-2-卤代苯甲酰胺的 5-exo-dig 环化,为以 30-75% 的产率合成各种 3-亚氨基异吲哚醇-1-酮提供了一种方便的途径。只需使用锌板代替石墨棒阳极,电合成的产物就通过芳基自由基介导的 5-exo-dig 环化和随后的还原氢化转化为不同的 3-氨基异吲哚英-1-酮。此外,这种负极材料确定的发散 5-exo-dig 环化具有温和的电化学条件、出色的衬底范围和良好的官能团耐受性。
更新日期:2024-11-06
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