Anamika Dhami, Sanoop P. Chandrasekharan, Kishor Mohanan
{"title":"BF3-Mediated C2-Amidation of Quinoline N-Oxides Employing Trifluorodiazoethane and Acetonitrile: Access to 2-N-(Trifluoroethyl)amidoquinolines","authors":"Anamika Dhami, Sanoop P. Chandrasekharan, Kishor Mohanan","doi":"10.1021/acs.orglett.4c04127","DOIUrl":null,"url":null,"abstract":"A Lewis acid-mediated C2-<i>N-</i>trifluoroethylamidation of quinolines, employing quinoline <i>N-</i>oxides, trifluorodiazoethane, and acetonitrile to forge a new class of <i>N-</i>(quinolin<i>-</i>2-yl)-<i>N-</i>(trifluoroethyl)acetamide is presented in this Letter. The reaction proceeds through a carbene generation/nitrile ylide formation/(3 + 2) cycloaddition/rearrangement cascade to furnish quinoline-2-<i>N-</i>(trifluoroethyl)acetamide derivatives in high yields.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"31 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04127","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A Lewis acid-mediated C2-N-trifluoroethylamidation of quinolines, employing quinoline N-oxides, trifluorodiazoethane, and acetonitrile to forge a new class of N-(quinolin-2-yl)-N-(trifluoroethyl)acetamide is presented in this Letter. The reaction proceeds through a carbene generation/nitrile ylide formation/(3 + 2) cycloaddition/rearrangement cascade to furnish quinoline-2-N-(trifluoroethyl)acetamide derivatives in high yields.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
