Guojian Fang, Xuan Wu, Xiaoyan Sang, Han Wang and Wenyan Hao*,
{"title":"Selective Construction of 2,4-Bisthioquinolines via Copper-Catalyzed Tandem Cyclization from o-Alkynylphenyl Isothiocyanates","authors":"Guojian Fang, Xuan Wu, Xiaoyan Sang, Han Wang and Wenyan Hao*, ","doi":"10.1021/acs.joc.4c0199110.1021/acs.joc.4c01991","DOIUrl":null,"url":null,"abstract":"<p >The selective synthesis of polysubstituted quinoline has been recognized as an important but highly challenging transformation. In this study, a highly efficient method for the synthesis of 2,4-bisthioquinolines has been developed through a copper(II)-promoted tandem cycloaddition of <i>o</i>-alkynylphenyl isothiocyanates, utilizing inexpensive and readily available sodium sulfide (Na<sub>2</sub>S) as the sulfur source. This transformation enables the direct synthesis of 2,4-bis(thioquinoline) heterocycles via the formation of C–C and C–S bonds in a one-pot reaction, demonstrating excellent tolerance for various functional groups.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 7","pages":"2811–2815 2811–2815"},"PeriodicalIF":3.3000,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.4c01991","RegionNum":2,"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
The selective synthesis of polysubstituted quinoline has been recognized as an important but highly challenging transformation. In this study, a highly efficient method for the synthesis of 2,4-bisthioquinolines has been developed through a copper(II)-promoted tandem cycloaddition of o-alkynylphenyl isothiocyanates, utilizing inexpensive and readily available sodium sulfide (Na2S) as the sulfur source. This transformation enables the direct synthesis of 2,4-bis(thioquinoline) heterocycles via the formation of C–C and C–S bonds in a one-pot reaction, demonstrating excellent tolerance for various functional groups.
期刊介绍：
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
