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银催化异腈的脱羧酰化反应:以空气作为唯一氧化剂合成α-酮酰胺

Silver-Catalyzed Decarboxylative Acylation of Isocyanides Accesses to α-Ketoamides with Air as a Sole Oxidant.

作者信息

Xu Jia, Li Xue, Chen Xing-Yu, He Yu-Ting, Lei Jie, Chen Zhong-Zhu, Xu Zhi-Gang

机构信息

College of Pharmacy, National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, IATTI, Chongqing University of Arts and Sciences, Chongqing 402160, China.

出版信息

Molecules. 2023 Jul 11;28(14):5342. doi: 10.3390/molecules28145342.

Abstract

α-Ketoamide moieties, as privileged units, may represent a valuable option to develop compounds with favorable biological activities, such as low toxicity, promising PK and drug-like properties. An efficient silver-catalyzed decarboxylative acylation of α-oxocarboxylic acids with isocyanides was developed to derivatize the α-ketoamide functional group via a multicomponent reaction (MCR) cascade sequence in one pot. A series of α-ketoamides was synthesized with three components of isocyanides, aromatic α-oxocarboxylic acid analogues and water in moderate yields. Based on the research, the silver-catalyzed decarboxylative acylation confirmed that an oxygen atom of the amide moiety was derived from the water and air as a sole oxidant for the whole process.

摘要

α-酮酰胺部分作为优势结构单元,可能是开发具有良好生物活性的化合物的一个有价值的选择,这些生物活性包括低毒性、良好的药代动力学性质和类药物特性。我们开发了一种高效的银催化α-氧代羧酸与异腈的脱羧酰化反应,通过多组分反应(MCR)级联序列在一锅法中衍生化α-酮酰胺官能团。以异腈、芳香族α-氧代羧酸类似物和水三种组分,以中等产率合成了一系列α-酮酰胺。基于该研究,银催化的脱羧酰化反应证实了酰胺部分的一个氧原子来源于水和空气,并且水和空气是整个过程唯一的氧化剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/aa43/10383724/29d170f505e1/molecules-28-05342-g001.jpg

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