{"title":"Denitrogenative thiolation of benzotriazinones: facile access to <i>ortho</i>-thiolated benzamides.","authors":"Dasari Chaithanya, Radhakrishnan Sakthiganapathi, Jaladi Jhansi, Ramaraju Korivi, Baburaj Baskar, Subramaniyan Mannathan","doi":"10.1039/d6ob01325b","DOIUrl":null,"url":null,"abstract":"<p><p>A metal-free denitrogenative thiolation of 1,2,3-benzotriazin-4(3<i>H</i>)-ones with thiols for the synthesis of <i>ortho</i>-thiolated benzamides in the presence of DBU is described. The reaction accommodates a broad range of <i>N</i>-aryl-substituted 1,2,3-benzotriazin-4(3<i>H</i>)-ones, as well as aryl and alkyl thiols, affording the desired products in moderate to high yields. The reaction is believed to proceed <i>via</i> a benzenediazonium intermediate. The scalability of the developed protocol was also further demonstrated.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8000,"publicationDate":"2026-10-20","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/d6ob01325b","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
A metal-free denitrogenative thiolation of 1,2,3-benzotriazin-4(3H)-ones with thiols for the synthesis of ortho-thiolated benzamides in the presence of DBU is described. The reaction accommodates a broad range of N-aryl-substituted 1,2,3-benzotriazin-4(3H)-ones, as well as aryl and alkyl thiols, affording the desired products in moderate to high yields. The reaction is believed to proceed via a benzenediazonium intermediate. The scalability of the developed protocol was also further demonstrated.
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.