Cascade Oxidation, Radical Addition, and Annulation of o‐Alkynylarylaldimine with Indole/Imidazopyridine: Access to Aromatic Heterocycle‐substituted Isoquinolines,Asian Journal of Organic Chemistry

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Cascade Oxidation, Radical Addition, and Annulation of o‐Alkynylarylaldimine with Indole/Imidazopyridine: Access to Aromatic Heterocycle‐substituted Isoquinolines
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-04-27 , DOI: 10.1002/ajoc.202000202
Yun‐Hui Zhao _{1,

2} , Yajun Yu ₁ , Dandan Hu ₁ , Lang Zhao ₁ , Wenlin Xie ₁ , Zhihua Zhou ₃

Affiliation

A peroxide‐mediated oxidation/radical addition/cyclization cascade reaction for the construction of isoquinoline skeleton is reported. The mild metal‐free promoted conditions of this reaction allowed us to synthesize a library of aromatic heterocycle‐substituted isoquinolines with a broad substrate scope, good functional group tolerance, and high atom economy in moderate to good yields. The radical intermediate in this reaction system was captured by TEMPO and confirmed by mass spectrometry (TOF‐MS). Further In vitro antiproliferative activities exhibited significant inhibition of the growth of HepG2, MCF‐7, MGC803 and EC‐9706 human cancer cell lines.

中文翻译：

邻-炔基芳基亚胺与吲哚/咪唑并吡啶的级联氧化，自由基加成和环化：获得芳香族杂环取代的异喹啉的方法

据报道，过氧化物介导的氧化/自由基加成/环化级联反应可用于构建异喹啉骨架。该反应在温和的无金属促进条件下进行，从而使我们能够合成具有宽范围底物范围，良好的官能团耐受性和高原子经济性的芳族杂环取代的异喹啉文库，产率中等至良好。TEMPO捕获了该反应系统中的自由基中间体，并通过质谱（TOF-MS）进行了确认。进一步的体外抗增殖活性显示出对HepG2，MCF-7，MGC803和EC-9706人癌细胞系生长的显着抑制作用。

更新日期：2020-04-27

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