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铜介导的β-羟基芳基烯胺酮与 3-吲哚乙酸的环化反应合成 3-吲哚甲基色酮。

Copper-Mediated Cyclization of -Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones.

机构信息

Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, 1023 South Shatai Road, Baiyun District, Guangzhou 510515, People's Republic of China.

出版信息

J Org Chem. 2022 Jul 15;87(14):9270-9281. doi: 10.1021/acs.joc.2c01005. Epub 2022 Jul 5.

Abstract

Here, we describe a copper-mediated tandem decarboxylative coupling/annulation protocol of -hydroxyaryl enaminones with 3-indoleacetic acids. A series of 3-indolmethyl-chromones were afforded in up to 97% yield. A one-pot method for 3-indolmethyl-chromones from -hydroxy acetophenones, , -dimethylformamide dimethyl acetal, and 3-indoleacetic acids was also developed. Derivatization of the products was conducted to provide various indolmethyl-substituted pyrimidines. Moreover, a biological evaluation revealed that some compounds had anti-influenza viral activities.

摘要

在这里,我们描述了一种铜介导的串联脱羧偶联/环化反应,该反应涉及β-羟基芳基烯胺酮与 3-吲哚乙酸的反应。以高达 97%的收率得到了一系列 3-吲哚甲基-色酮。我们还开发了一种从β-羟基苯乙酮、二甲基甲酰胺二甲缩醛、3-吲哚乙酸一锅法制备 3-吲哚甲基-色酮的方法。对产物进行了衍生化,得到了各种吲哚甲基取代的嘧啶。此外,生物评价表明,一些化合物具有抗流感病毒活性。

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