Catalyst‐free Sequential Wolff Rearrangement and [3+3] Annulation of Enaminones and Diazo compounds Enabling the Assembly of Highly Functionalized Pyridin‐4‐ones

IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-01-16 DOI:10.1002/adsc.202401561
Yunzheng Wei, Longkun Chen, Huimin Hu, Yu Zhang, Shaolin Yang, Yu Xu, Li Chen, Fuchao Yu
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Abstract

A general protocol for the efficient synthesis of a variety of highly functionalized pyridin‐4‐ones has been developed through a sequential Wolff rearrangement and [3+3] annulation reaction of enaminones and diazo compounds. This straightforward approach features wide substrate applicability, good substrate tolerance, moderate to excellent yields, and without any catalyst, and enables access to structurally diverse pyridin‐4‐one skeletons. Additionally, scale‐up experiments and synthetic derivatizations demonstrated the potential synthetic utility of the transformations.
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氨基酮和重氮化合物的无催化剂序列Wolff重排和[3+3]环化使高功能化吡啶- 4 -化合物的组装成为可能
通过连续的Wolff重排和胺酮和重氮化合物的[3+3]环化反应,开发了一种高效合成各种高功能化吡啶- 4 -酮的通用方案。这种简单的方法具有广泛的底物适用性,良好的底物耐受性,中等到优异的产率,并且不需要任何催化剂,并且可以获得结构多样的吡啶- 4 - 1骨架。此外,放大实验和合成衍生化证明了转换的潜在综合效用。
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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