One-pot synthesis of symmetrical bis-sulfonyl 2,6-diarylpyridines via BiCl3-catalyzed and K2S2O8-mediated domino annulation of β-ketosulfones and N,N-dimethylacetamide.
{"title":"One-pot synthesis of symmetrical bis-sulfonyl 2,6-diarylpyridines <i>via</i> BiCl<sub>3</sub>-catalyzed and K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-mediated domino annulation of β-ketosulfones and <i>N</i>,<i>N</i>-dimethylacetamide.","authors":"Meng-Yang Chang, Chun-Yi Lin","doi":"10.1039/d4ob01681e","DOIUrl":null,"url":null,"abstract":"<p><p>In this study, BiCl<sub>3</sub>-promoted and K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-mediated synthesis of diverse bis-sulfonyl 2,6-diarypyridines was developed <i>via</i> one-pot stepwise (2C + 2C + 1C + 1N) annulation of two molecules of β-ketosulfone and <i>N</i>,<i>N</i>-dimethylacetamide (DMAC). In the entire process, DMAC acts as the synthon of one carbon and one nitrogen in the construction of the pyridine skeleton <i>via</i> cascade formation of single (C-C/C-N) and double (CC/CN) bonds under refluxing DMAC conditions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2024-12-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01681e","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
In this study, BiCl3-promoted and K2S2O8-mediated synthesis of diverse bis-sulfonyl 2,6-diarypyridines was developed via one-pot stepwise (2C + 2C + 1C + 1N) annulation of two molecules of β-ketosulfone and N,N-dimethylacetamide (DMAC). In the entire process, DMAC acts as the synthon of one carbon and one nitrogen in the construction of the pyridine skeleton via cascade formation of single (C-C/C-N) and double (CC/CN) bonds under refluxing DMAC conditions.
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.