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通过C-H键活化氧化偶联由酰苯胺与苯乙烯基酮直接合成查耳酮

Direct Synthesis of Chalcones from Anilides with Phenyl Vinyl Ketones by Oxidative Coupling Through C-H Bond Activation.

作者信息

Maegawa Tomohiro, Mizui Ryota, Urasaki Miki, Fujimura Kazuma, Nakamura Akira, Miki Yasuyoshi

机构信息

School of Pharmaceutical Sciences, Kindai University, Higashi-osaka, Osaka 577-8502, Japan.

Research Organization of Science and Technology, Research Center for Drug Discovery and Pharmaceutical Science, Ritsumeikan University, Nojihigashi, Kusatsu, Shiga 525-8577, Japan.

出版信息

ACS Omega. 2018 May 18;3(5):5375-5381. doi: 10.1021/acsomega.8b00594. eCollection 2018 May 31.

DOI:10.1021/acsomega.8b00594
PMID:31458746
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6641892/
Abstract

A novel approach for synthesizing chalcones by Pd-catalyzed oxidative coupling is described. This is the first report of the efficient coupling reaction of acetanilides with phenyl vinyl ketones under mild conditions. Selective C-H activation occurred next to the acetamide group to afford 2-aminochalcone derivatives. The reaction proceeded under an O atmosphere without any chemical co-oxidants.

摘要

描述了一种通过钯催化氧化偶联合成查耳酮的新方法。这是关于乙酰苯胺与苯乙烯基酮在温和条件下有效偶联反应的首次报道。在乙酰酰胺基团旁边发生选择性C-H活化,得到2-氨基查耳酮衍生物。该反应在氧气气氛下进行,无需任何化学共氧化剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d25/6641892/2b4b07039383/ao-2018-00594n_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d25/6641892/aed027dd71f2/ao-2018-00594n_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d25/6641892/2b4b07039383/ao-2018-00594n_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d25/6641892/aed027dd71f2/ao-2018-00594n_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d25/6641892/2b4b07039383/ao-2018-00594n_0002.jpg

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Synthesis of 3-acylindoles by oxidative rearrangement of 2-aminochalcones using a hypervalent iodine reagent and cyclization sequence.使用高价碘试剂通过2-氨基查耳酮的氧化重排和环化序列合成3-酰基吲哚。
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Chalcone: A Privileged Structure in Medicinal Chemistry.
Efficient Approach for the Synthesis of Aryl Vinyl Ketones and Its Synthetic Application to Mimosifoliol with DFT and Autodocking Studies.
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