Catalyst‐free Sequential Wolff Rearrangement and [3+3] Annulation of Enaminones and Diazo compounds Enabling the Assembly of Highly Functionalized Pyridin‐4‐ones
{"title":"Catalyst‐free Sequential Wolff Rearrangement and [3+3] Annulation of Enaminones and Diazo compounds Enabling the Assembly of Highly Functionalized Pyridin‐4‐ones","authors":"Yunzheng Wei, Longkun Chen, Huimin Hu, Yu Zhang, Shaolin Yang, Yu Xu, Li Chen, Fuchao Yu","doi":"10.1002/adsc.202401561","DOIUrl":null,"url":null,"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.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"27 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401561","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
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.
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.