Copper-Catalyzed Reductive Ring-Cleavage of Isoxazoles: Synthesis of Fluoroalkylated Enaminones and Application for the Preparation of Celecoxib, Deracoxib, and Mavacoxib,The Journal of Organic Chemistry

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Copper-Catalyzed Reductive Ring-Cleavage of Isoxazoles: Synthesis of Fluoroalkylated Enaminones and Application for the Preparation of Celecoxib, Deracoxib, and Mavacoxib
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-02-15 , DOI: 10.1021/acs.joc.0c02980
Chao Wan ₁ , Jian-Yu Pang ₁ , Wei Jiang ₂ , Xiao-Wei Zhang _{1,

3} , Xiang-Guo Hu _{1,

4}

Affiliation

We have identified a new reactivity of copper/diamine catalysis for the reductive ring-cleavage of isoxazoles to yield fluoroalkylated enaminones. This protocol has the advantage of using commercially available reagents, ease of setting up, broad tolerance of functionality, and is regiospecific and free of defluorination and reduction of reducible functional groups. The utility was demonstrated by a one-step, regioselective synthesis of fluoroalkylated pyrazole-based drugs such as celecoxib, deracoxib, and mavacoxib.

中文翻译：

铜催化的异恶唑的还原环裂解：氟代烷基化的烯胺酮的合成及其在制备塞来昔布，德拉曲昔和马伐昔布中的应用

我们已经发现了铜/二胺催化的新反应性，用于异恶唑的还原性环裂解，以生成氟代烷基化的烯胺酮。该方案的优点是使用可商购的试剂，易于设置，功能广泛，并且具有区域特异性，并且不存在脱氟和可还原官能团的还原。氟烷基化吡唑类药物（如塞来昔布，德拉可昔布和马vacoxib）的一步式区域选择性合成证明了其实用性。

更新日期：2021-03-19

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