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A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-Ester Acceptors Using a Desaturative Amination–Cyclization Approach
Synthesis ( IF 2.6 ) Pub Date : 2021-06-28 , DOI: 10.1055/a-1538-8429
Henry P. Caldora 1 , Sebastian Govaerts 1 , Daniele Leonori 1 , Shashikant U. Dighe 1 , Oliver J. Turner 2
Affiliation  

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.

中文翻译:

使用去饱和胺化-环化方法从环己酮衍生的 γ-酮-酯受体从头合成羟吲哚

在这里,我们报告了羟吲哚合成的去饱和方法。该方法使用简单的 2-(2-氧代环己基)乙酸乙酯和伯胺结构单元作为偶联伙伴。双光氧化还原-钴歧管用于生成二级苯胺,在加热时,该苯胺与悬垂的酯官能团发生环化。该过程在温和的条件下运行,并应用于几种氨基酸的修饰、重磅炸弹药物美西律,以及二氢喹啉酮的形成。
更新日期:2021-08-05
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