Juan Tian, Mengyun Chen, Xinyi Wang, Xin Chen, Chengya Shao, Yiting Xiong, Yunfeng Liu, Dayong Sang
{"title":"One-pot synthesis of <i>N</i>-sulfonylamidines from <i>N</i>-acylsulfonamides enabled by a metal triflate-mediated nonhydrolytic <i>N</i>-deacylation.","authors":"Juan Tian, Mengyun Chen, Xinyi Wang, Xin Chen, Chengya Shao, Yiting Xiong, Yunfeng Liu, Dayong Sang","doi":"10.1039/d4ob01296h","DOIUrl":null,"url":null,"abstract":"<p><p>A triflate salt-catalyzed nonhydrolytic method for the deacylation of <i>N</i>-acylsulfonamides and subsequent one-pot condensation of the newly formed sulfonamides with <i>N</i>,<i>N</i>-dimethylformamide dimethyl acetal to provide <i>N</i>-sulfonylamidines is presented. A range of aliphatic and aromatic <i>N</i>-acylsulfonamides bearing various <i>N</i>-acyl groups such as acetyl, propionyl, butyrl, isobutyryl, octanoyl, benzoyl, 2-phenylacetyl, and sterically hindered pivaloyl are readily transformed into the corresponding <i>N</i>-sulfonylamidines in good to excellent yields. A variety of functional groups including halogeno, keto, nitro, cyano, hydroxyl, ether, and carboxylic ester are tolerated intact.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-10-09","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/d4ob01296h","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 triflate salt-catalyzed nonhydrolytic method for the deacylation of N-acylsulfonamides and subsequent one-pot condensation of the newly formed sulfonamides with N,N-dimethylformamide dimethyl acetal to provide N-sulfonylamidines is presented. A range of aliphatic and aromatic N-acylsulfonamides bearing various N-acyl groups such as acetyl, propionyl, butyrl, isobutyryl, octanoyl, benzoyl, 2-phenylacetyl, and sterically hindered pivaloyl are readily transformed into the corresponding N-sulfonylamidines in good to excellent yields. A variety of functional groups including halogeno, keto, nitro, cyano, hydroxyl, ether, and carboxylic ester are tolerated intact.