Dearomative Transformation of Pyridin-3-ols into 2,3,6,7-Tetrahydro-1H-2,6-methanobenzo[d]azonin-12-ones via Oxidopyridinium/o-Quinodimethane (5 + 4) Cycloaddition
{"title":"Dearomative Transformation of Pyridin-3-ols into 2,3,6,7-Tetrahydro-1H-2,6-methanobenzo[d]azonin-12-ones via Oxidopyridinium/o-Quinodimethane (5 + 4) Cycloaddition","authors":"Yoshihiko Yamamoto, Yuto Ide, Takeshi Yasui","doi":"10.1021/acs.orglett.4c03878","DOIUrl":null,"url":null,"abstract":"We report the dearomative transformation of pyridin-3-ols via oxidopyridinium (5 + 4) cycloaddition with <i>o</i>-quinodimethanes, leading to 2,3,6,7-tetrahydro-1<i>H</i>-2,6-methanobenzo[<i>d</i>]azonin-12-ones. The chemoselective derivatization of the obtained cycloadduct was also investigated to demonstrate the synthetic potential of the obtained cycloadduct.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-23","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.4c03878","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
We report the dearomative transformation of pyridin-3-ols via oxidopyridinium (5 + 4) cycloaddition with o-quinodimethanes, leading to 2,3,6,7-tetrahydro-1H-2,6-methanobenzo[d]azonin-12-ones. The chemoselective derivatization of the obtained cycloadduct was also investigated to demonstrate the synthetic potential of the obtained cycloadduct.
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.