{"title":"Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones","authors":"Jing‐Tong Deng , Ming Lang , Jin‐Bao Peng","doi":"10.1002/adsc.202400849","DOIUrl":null,"url":null,"abstract":"<div><div>The transition metal catalyzed cyclization of alkene‐tethered carbamoyl chloride has emerged as a tool to construct oxindoles bearing quaternary centers. Most of these reactions proceed via carbometalation‐initiated 5‐<em>exo</em>‐trig cyclization followed by nucleophilic trapping of the resulting <em>σ</em> alkyl‐metal species to achieve diverse functionalized oxindoles. The 6‐<em>endo</em>‐trig type cyclization of alkene‐tethered carbamoyl chloride has been rarely reported. Herein, a zinc‐mediated carbamoyl amination of alkylidenecyclopropane‐tethered carbamoyl chlorides with anilines for the synthesis of functionalized 2‐quinolones was developed. A range of different substituted 2‐quinolones were prepared in 65–89% yield from alkylidenecyclopropane‐tethered carbamoyl chlorides and aniline derivatives using a Zn/TMSCl system.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4644-4648"},"PeriodicalIF":4.4000,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1615415024005272","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
The transition metal catalyzed cyclization of alkene‐tethered carbamoyl chloride has emerged as a tool to construct oxindoles bearing quaternary centers. Most of these reactions proceed via carbometalation‐initiated 5‐exo‐trig cyclization followed by nucleophilic trapping of the resulting σ alkyl‐metal species to achieve diverse functionalized oxindoles. The 6‐endo‐trig type cyclization of alkene‐tethered carbamoyl chloride has been rarely reported. Herein, a zinc‐mediated carbamoyl amination of alkylidenecyclopropane‐tethered carbamoyl chlorides with anilines for the synthesis of functionalized 2‐quinolones was developed. A range of different substituted 2‐quinolones were prepared in 65–89% yield from alkylidenecyclopropane‐tethered carbamoyl chlorides and aniline derivatives using a Zn/TMSCl system.
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.