Fe(OTf)3-catalyzed annulation of α,β-unsaturated ketoxime acetates with enaminones for the synthesis of functionalized 2,4-diarylpyridines,Organic Chemistry Frontiers

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Fe(OTf)3-catalyzed annulation of α,β-unsaturated ketoxime acetates with enaminones for the synthesis of functionalized 2,4-diarylpyridines
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2023-07-22 , DOI: 10.1039/d3qo00685a
Xing-Mei Hu ₁ , Jing Yang ₁ , Jia-Ming Yang ₁ , Bi-Na Shao ₁ , Rong Huang ₁ , Sheng-Jiao Yan ₁

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Herein, we present a novel method for the synthesis of highly functionalized 2,4-diarylpyridines. This method involves a one-pot cascade reaction utilizing α,β-unsaturated ketoxime acetates and enaminones as substrates, encompassing a SET, Michael reaction, oxidation of allyl group carbon, and loss of one proton and one PhNH₂. The reaction occurred by refluxing a mixture of the starting materials in toluene with the catalyst Fe(OTf)₃, leading to the formation and cleavage of two bonds. The cascade reaction generates a series of functionalized pyridines. Notably, this method enables the synthesis of functionalized asymmetrical 2,4-diarylpyridines and offers an efficient alternative to the tedious multi-step syntheses traditionally employed. This approach is suitable for the combinatorial and parallel syntheses of pyridine derivatives in a one-pot reaction.

中文翻译：

Fe(OTf)3 催化 α,β-不饱和酮肟乙酸酯与烯胺酮成环，用于合成功能化 2,4-二芳基吡啶

在此，我们提出了一种合成高功能化2,4-二芳基吡啶的新方法。该方法涉及利用α,β-不饱和酮肟乙酸酯和烯胺酮作为底物的一锅级联反应，包括SET、迈克尔反应、烯丙基碳的氧化以及一个质子和一个PhNH 2 的_损失。该反应通过将起始原料在甲苯中的混合物与催化剂Fe(OTf) _{3回流来发生}，导致两个键的形成和断裂。级联反应产生一系列官能化吡啶。值得注意的是，该方法能够合成功能化的不对称 2,4-二芳基吡啶，并为传统上采用的繁琐的多步骤合成提供了有效的替代方案。该方法适用于一锅反应中吡啶衍生物的组合和平行合成。

更新日期：2023-07-25

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