{"title":"Scope and limitations of the preparation of xanthones using Eaton's reagent.","authors":"Johann Bosson","doi":"10.55730/1300-0527.3624","DOIUrl":null,"url":null,"abstract":"<p><p>Xanthones comprise a large family of heterocycles displaying fascinating biological properties. Many synthetic protocols have been developed for the preparation of natural and nonnatural xanthone derivatives. Among them, condensation reactions between salicylic acid derivatives and phenol partners are highly desirable. Those reactions can be satisfactorily performed using Eaton's reagent (P<sub>2</sub>O<sub>5</sub> in CH<sub>3</sub>SO<sub>3</sub>H). Despite being highly effective with a variety of substrates, this approach presents limitations that depend on the electronic nature of the reaction precursors. The scope and limitations of the Eaton's reagent-mediated preparation of xanthones are herein presented and discussed. In short, this approach is limited to the utilization of very electron-rich phenol substrates (like phloroglucinol compounds), or to electron-rich phenol precursors (like resorcinol derivatives) via the isolation of benzophenone intermediates in this latter case. Electron-poor phenols are not amenable to this transformation with Eaton's reagent.</p>","PeriodicalId":23367,"journal":{"name":"Turkish Journal of Chemistry","volume":null,"pages":null},"PeriodicalIF":1.3000,"publicationDate":"2023-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10965184/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Turkish Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.55730/1300-0527.3624","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2023/1/1 0:00:00","PubModel":"eCollection","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Xanthones comprise a large family of heterocycles displaying fascinating biological properties. Many synthetic protocols have been developed for the preparation of natural and nonnatural xanthone derivatives. Among them, condensation reactions between salicylic acid derivatives and phenol partners are highly desirable. Those reactions can be satisfactorily performed using Eaton's reagent (P2O5 in CH3SO3H). Despite being highly effective with a variety of substrates, this approach presents limitations that depend on the electronic nature of the reaction precursors. The scope and limitations of the Eaton's reagent-mediated preparation of xanthones are herein presented and discussed. In short, this approach is limited to the utilization of very electron-rich phenol substrates (like phloroglucinol compounds), or to electron-rich phenol precursors (like resorcinol derivatives) via the isolation of benzophenone intermediates in this latter case. Electron-poor phenols are not amenable to this transformation with Eaton's reagent.
期刊介绍:
The Turkish Journal of Chemistry is a bimonthly multidisciplinary journal published by the Scientific and Technological Research Council of Turkey (TÜBİTAK).
The journal is dedicated to dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, polymeric, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences especially in chemical engineering where molecular aspects are key to the findings.
The journal accepts English-language original manuscripts and contribution is open to researchers of all nationalities.
The journal publishes refereed original papers, reviews, letters to editor and issues devoted to special fields.
All manuscripts are peer-reviewed and electronic processing ensures accurate reproduction of text and data, plus publication times as short as possible.