{"title":"底物诱导的n-烷基苯胺双利用级联反应:高位点选择性可持续合成[4,3-b]喹啉-6-酮。","authors":"Zhou Zhang , Sihan Zhao , Yuanmin Wen , Guiyun Zeng , Minglong Yuan , Chao Huang","doi":"10.1039/d4ob01764a","DOIUrl":null,"url":null,"abstract":"<div><div>We describe a novel substrate-induced cascade reaction of <em>N</em>-alkyl anilines <em>via</em> C(sp<sup>3</sup>)–N bond cleavage and reorganization into chromeno[4,3-<em>b</em>]quinolin-6-ones. <em>N</em>-alkyl anilines are not only used as a carbon source, but also the waste group was trapped by 4-hydroxy coumarin. The calculation of green metrics shows that our protocol is more efficient and green with lower emission than before. Additionally, a gram-scale reaction and one-pot synthesis of bioactive molecules further demonstrate the potential application of our protocol in the pharmaceutical industry.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 4","pages":"Pages 884-891"},"PeriodicalIF":2.7000,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A substrate-induced dual utilization cascade reaction of N-alkyl anilines: highly site-selective sustainable synthesis of chromeno[4,3-b]quinolin-6-ones†\",\"authors\":\"Zhou Zhang , Sihan Zhao , Yuanmin Wen , Guiyun Zeng , Minglong Yuan , Chao Huang\",\"doi\":\"10.1039/d4ob01764a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>We describe a novel substrate-induced cascade reaction of <em>N</em>-alkyl anilines <em>via</em> C(sp<sup>3</sup>)–N bond cleavage and reorganization into chromeno[4,3-<em>b</em>]quinolin-6-ones. <em>N</em>-alkyl anilines are not only used as a carbon source, but also the waste group was trapped by 4-hydroxy coumarin. The calculation of green metrics shows that our protocol is more efficient and green with lower emission than before. Additionally, a gram-scale reaction and one-pot synthesis of bioactive molecules further demonstrate the potential application of our protocol in the pharmaceutical industry.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"23 4\",\"pages\":\"Pages 884-891\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-11-22\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024010577\",\"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://www.sciencedirect.com/org/science/article/pii/S1477052024010577","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
A substrate-induced dual utilization cascade reaction of N-alkyl anilines: highly site-selective sustainable synthesis of chromeno[4,3-b]quinolin-6-ones†
We describe a novel substrate-induced cascade reaction of N-alkyl anilines via C(sp3)–N bond cleavage and reorganization into chromeno[4,3-b]quinolin-6-ones. N-alkyl anilines are not only used as a carbon source, but also the waste group was trapped by 4-hydroxy coumarin. The calculation of green metrics shows that our protocol is more efficient and green with lower emission than before. Additionally, a gram-scale reaction and one-pot synthesis of bioactive molecules further demonstrate the potential application of our protocol in the pharmaceutical industry.
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.