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在氧化还原中性条件下，通过酮肟乙酸酯与三氟乙酰苯胺的铜催化环化反应制备4-三氟甲基喹啉。

Access to 4-Trifluoromethyl Quinolines via Cu-Catalyzed Annulation Reaction of Ketone Oxime Acetates with -Trifluoroacetyl Anilines under Redox-Neutral Conditions.

作者信息

Wang Zhen-Hua, Shen Li-Wen, Yang Ping, You Yong, Zhao Jian-Qiang, Yuan Wei-Cheng

机构信息

Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu 610106, China.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

出版信息

J Org Chem. 2022 May 6;87(9):5804-5816. doi: 10.1021/acs.joc.2c00128. Epub 2022 Apr 27.

DOI:10.1021/acs.joc.2c00128
PMID:35475619
Abstract

An efficient Cu-catalyzed annulation reaction of ketone oxime acetates with -trifluoroacetyl anilines has been disclosed. With the developed protocol, a series of 4-trifluoromethyl quinolines were obtained in good to excellent yields (58-99%) under redox-neutral conditions. The protocol also could be extended to ferrocene-based ketone oxime acetates for the construction of ferrocene-substituted fluorine-containing quinolines.

摘要

已公开了一种高效的铜催化的酮肟乙酸酯与三氟乙酰苯胺的环化反应。采用所开发的方法，在氧化还原中性条件下，以良好至优异的产率（58-99%）获得了一系列4-三氟甲基喹啉。该方法还可扩展至基于二茂铁的酮肟乙酸酯，用于构建二茂铁取代的含氟喹啉。

相似文献

1
Access to 4-Trifluoromethyl Quinolines via Cu-Catalyzed Annulation Reaction of Ketone Oxime Acetates with -Trifluoroacetyl Anilines under Redox-Neutral Conditions.在氧化还原中性条件下，通过酮肟乙酸酯与三氟乙酰苯胺的铜催化环化反应制备4-三氟甲基喹啉。
J Org Chem. 2022 May 6;87(9):5804-5816. doi: 10.1021/acs.joc.2c00128. Epub 2022 Apr 27.
2
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Copper-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate.铜催化的α,β-不饱和酮肟乙酸酯与三氟丙酮酸乙酯的[4+2]氧化环加成反应。
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Iron-Catalysed [3+3] Annulation of Oxime Acetates and Enaminones towards the Synthesis of Multi-Substituted Pyridines.铁催化肟乙酸酯和烯胺酮的[3+3]环化反应合成多取代吡啶
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