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过氧单硫酸盐促进的芳基甘氨酸衍生物的脱氢Povarov环化反应:一种合成喹啉稠合内酯和内酰胺的方法。

Oxone promoted dehydrogenative Povarov cyclization of -aryl glycine derivatives: an approach towards quinoline fused lactones and lactams.

作者信息

More Devidas A, Shinde Ganesh H, Shaikh Aslam C, Muthukrishnan M

机构信息

Division of Organic Chemistry, CSIR-National Chemical Laboratory Pune 411008 India

Academy of Scientific and Innovative Research (AcSIR) Ghaziabad 201002 India.

出版信息

RSC Adv. 2019 Sep 25;9(52):30277-30291. doi: 10.1039/c9ra06212b. eCollection 2019 Sep 23.

Abstract

Oxone promoted intramolecular dehydrogenative imino Diels-Alder reaction (Povarov cyclization) of alkyne tethered -aryl glycine esters and amides has been explored, thus affording biologically significant quinoline fused lactones and lactams. The reaction is simple, scalable, and high yielding (up to 88%). The method was further extended to prepare biologically important luotonin-A analogues and the quinoline core of uncialamycin.

摘要

已对过氧单硫酸盐促进的炔烃连接的芳基甘氨酸酯和酰胺的分子内脱氢亚氨基狄尔斯-阿尔德反应(波瓦罗夫环化反应)进行了探索,从而得到了具有生物学意义的喹啉稠合内酯和内酰胺。该反应简单、可扩展且产率高(高达88%)。该方法进一步扩展用于制备具有生物学重要性的路托宁-A类似物和安卡霉素的喹啉核心。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/298a/9072217/2ab7573ebd17/c9ra06212b-f1.jpg

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