Juan Tian, Mengyun Chen, Xinyi Wang, Xin Chen, Chengya Shao, Yiting Xiong, Yunfeng Liu, Dayong Sang
{"title":"通过金属三late 介导的非水解 N-脱酰基反应,从 N-酰基磺酰胺中一次性合成 N-磺酰胺。","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":"{\"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}","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}
One-pot synthesis of N-sulfonylamidines from N-acylsulfonamides enabled by a metal triflate-mediated nonhydrolytic N-deacylation.
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.