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通过铑(III)催化的1-苯基吡唑烷酮与炔基环丁醇的可调氧化还原中性偶联选择性合成吡唑并[1,2 - ]吡唑啉酮和2-酰基吲哚。

Selective Synthesis of Pyrazolo[1,2-]pyrazolones and 2-Acylindoles via Rh(III)-Catalyzed Tunable Redox-Neutral Coupling of 1-Phenylpyrazolidinones with Alkynyl Cyclobutanols.

作者信息

Xu Yuanshuang, Shen Mengyang, Zhang Xinying, Fan Xuesen

机构信息

Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

出版信息

Org Lett. 2020 Jun 19;22(12):4697-4702. doi: 10.1021/acs.orglett.0c01475. Epub 2020 May 28.

Abstract

An unprecedented divergent synthesis of pyrazolo[1,2-]pyrazolones and 2-acylindoles via Rh(III)-catalyzed [4 + 1] or [3 + 2] annulation of 1-phenylpyrazolidinones with alkynyl cyclobutanols through redox-neutral multiple bond activation by using -NH and -OH units as directing groups is presented. Notably, different annulation reactions were selectively achieved by simply adjusting the reaction conditions. With features such as simple procedures, easily accessible substrates, and high regio/chemoselectivity, these methods may find wide applications in related areas.

摘要

报道了一种前所未有的吡唑并[1,2 - ]吡唑啉酮和2 - 酰基吲哚的发散性合成方法,该方法通过Rh(III)催化1 - 苯基吡唑烷酮与炔基环丁醇进行[4 + 1]或[3 + 2]环化反应,利用 -NH和 -OH单元作为导向基团通过氧化还原中性的多键活化实现。值得注意的是,通过简单调整反应条件可选择性地实现不同的环化反应。这些方法具有操作简单、底物易于获得以及区域/化学选择性高等特点,可能在相关领域得到广泛应用。

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