Vladimir L. Bondarev, Alexey A. Festa, Olga A. Storozhenko, Vladimir A. Kokorekin, Anton P. Novikov, Alexey V. Varlamov, Leonid G. Voskressensky
{"title":"Electrochemical Synthesis of 3-(Sulfonyl)quinol-4-ones from o-Alkynyl-N-(formyl)anilides and Sulfinates","authors":"Vladimir L. Bondarev, Alexey A. Festa, Olga A. Storozhenko, Vladimir A. Kokorekin, Anton P. Novikov, Alexey V. Varlamov, Leonid G. Voskressensky","doi":"10.1021/acs.orglett.4c04209","DOIUrl":null,"url":null,"abstract":"Electrolysis of <i>o</i>-alkynyl-<i>N</i>-(formyl)anilides and sodium sulfinates on graphite electrodes delivers biologically sound 3-(sulfonyl)quinol-4-ones with moderate to good yields. The reaction is carried out in an undivided cell in the presence of silver(I) oxide with potassium iodide or sodium tetrafluoroborate as the supporting electrolyte. The reaction tolerates variously substituted anilides as well as aryl and alkyl sulfinates. The transformation proceeds as a domino sequence of oxysulfonylation and cyclocondensation steps.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"70 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-25","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.4c04209","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
Electrolysis of o-alkynyl-N-(formyl)anilides and sodium sulfinates on graphite electrodes delivers biologically sound 3-(sulfonyl)quinol-4-ones with moderate to good yields. The reaction is carried out in an undivided cell in the presence of silver(I) oxide with potassium iodide or sodium tetrafluoroborate as the supporting electrolyte. The reaction tolerates variously substituted anilides as well as aryl and alkyl sulfinates. The transformation proceeds as a domino sequence of oxysulfonylation and cyclocondensation steps.
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.