{"title":"One-pot synthesis of diaroyl benzothiepine-1,1-dioxides†","authors":"Meng-Yang Chang and Nai-Chen Hsueh","doi":"10.1039/D5OB00198F","DOIUrl":null,"url":null,"abstract":"<p >We report the one-pot two-step synthesis of diaroyl benzothiepine-1,1-dioxides <em>via</em> rongalite-mediated double sulfination of α-bromoacetophenones followed by double condensation of the resulting 1,3-diaroyl sulfones and <em>o</em>-phthalaldehydes. In the (1C + 1C + 1S + 4C) reaction process, a seven-membered ring system could be constructed by two carbon–sulfur (C–S) single bonds and two carbon–carbon double bonds (C<img>C) under mild conditions. A related putative mechanism is proposed and discussed in this article.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 15","pages":" 3572-3582"},"PeriodicalIF":2.9000,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/ob/d5ob00198f","RegionNum":3,"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 one-pot two-step synthesis of diaroyl benzothiepine-1,1-dioxides via rongalite-mediated double sulfination of α-bromoacetophenones followed by double condensation of the resulting 1,3-diaroyl sulfones and o-phthalaldehydes. In the (1C + 1C + 1S + 4C) reaction process, a seven-membered ring system could be constructed by two carbon–sulfur (C–S) single bonds and two carbon–carbon double bonds (CC) under mild conditions. A related putative mechanism is proposed and discussed in this article.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.