Visible‐light‐mediated Synthesis of Bromo‐containing Azaspirotrienediones from N‐phenylpropynamides,Asian Journal of Organic Chemistry

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Visible‐light‐mediated Synthesis of Bromo‐containing Azaspirotrienediones from N‐phenylpropynamides
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2021-01-11 , DOI: 10.1002/ajoc.202000728
Yuan Chen ₁ , Fo-Yun Lu ₁ , Rui-Xue Li ₁ , Zhi Guan ₁ , Yan-Hong He ₂

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A visible‐light‐mediated reaction of N‐phenylpropynamides with diethyl 2,2‐dibromomalonate for the synthesis of bromo‐substituted azaspirotrienediones has been developed. This method allows the formation of C−Br, C−C and C=O bonds in one pot via a cascade radical addition/ipso‐cyclization/oxidation process. A possible radical mechanism involving single electron transfer and energy transfer processes is proposed based on control experiments, cyclic voltammetry determination and Stern‐Volmer quenching experiments.

中文翻译：

N-苯基丙炔酰胺的可见光介导的含溴氮杂螺三烯二酮的合成

已开发出N-苯基丙酰胺与2,2-二溴丙二酸二乙酯的可见光介导反应，用于合成溴取代的氮杂螺三烯二酮。该方法允许通过级联自由基加成/内环化/氧化过程在一个罐中形成C-Br，CC和C = O键。在控制实验，循环伏安法测定和斯特恩-沃尔默猝灭实验的基础上，提出了可能的涉及单电子转移和能量转移过程的自由基机理。

更新日期：2021-03-11

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