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β-酮酰胺的串联氧化α-羟基化/β-缩醛化反应及其应用

Tandem Oxidative α-Hydroxylation/β-Acetalization Reaction of β-Ketoamides and Its Applications.

作者信息

Zhang Zhiguo, Gao Xiaolong, Yu Haifeng, Bi Jingjing, Zhang Guisheng

机构信息

Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Henan Normal University, 46# East of Construction Road, Xinxiang, Henan 453007, China.

Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Northeast Normal University, Changchun, Jilin 130024, China.

出版信息

ACS Omega. 2017 Nov 9;2(11):7746-7754. doi: 10.1021/acsomega.7b01526. eCollection 2017 Nov 30.

Abstract

A tandem oxidative α-hydroxylation/β-acetalization reaction of β-ketoamides was developed in the presence of PIDA and NaOH. This reaction proceeded at 25 °C in the absence of a metal catalyst to provide 2-hydroxy-3,3-dimethoxy--substituted butanamides in good to excellent yields from readily available starting materials. The application of this chemistry to the construction of α-hydroxy-β-ketoamides and quinolinones was also described.

摘要

在碘代二乙酸(PIDA)和氢氧化钠存在的情况下,开发了一种β-酮酰胺的串联氧化α-羟基化/β-缩醛化反应。该反应在25℃下,在无金属催化剂的条件下进行,以容易获得的起始原料,高收率地提供2-羟基-3,3-二甲氧基-β-取代的丁酰胺。还描述了这种化学方法在构建α-羟基-β-酮酰胺和喹啉酮方面的应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9b8b/6645376/b51d9aa77dc7/ao-2017-01526e_0002.jpg

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