A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-Ester Acceptors Using a Desaturative Amination-Cyclization Approach
A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-Ester Acceptors Using a Desaturative Amination-Cyclization Approach
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DOI：
10.1055/a-1538-8429
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发表时间：
2021-06-28
影响因子：
2.6
通讯作者：
Leonori, Daniele
中科院分区：
文献类型：
--
作者：
Caldora, Henry P.;Govaerts, Sebastian;Leonori, Daniele
在这里，我们报告了一种氧吲哚合成的不饱和方法。该方法使用简单的2-（2-氧环己基）乙酸乙酯和伯胺作为偶联伙伴。双光氧化还原钴歧管用于产生仲苯胺，加热后，与悬垂酯功能循环。该过程在温和的条件下进行，并应用于几种氨基酸的修饰，重磅药物美西汀，以及二氢喹啉酮的形成。
Here we report a desaturative approach for oxindole synthesis. This method uses simple ethyl 2-(2-oxocyclohexyl)acetates and primary amine building blocks as coupling partners. A dual photoredox-cobalt manifold is used to generate a secondary aniline that, upon heating, cyclizes with the pendent ester functionality. The process operates under mild conditions and was applied to the modification of several amino acids, the blockbuster drug mexiletine, as well as the formation of dihydroquinolinones.