Copper-catalyzed tandem cyclization reaction of ethynylbenzoxazinones and thiols: facile construction of 2-thiomethylene indoles†

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-09-16 Epub Date: 2024-09-18 DOI:10.1039/d4ob01164c
Lei Song , Fu-Qiang Li , Xiao-Han Qiu , Guo-Zhen Wei , Hui-Yu Chen , Ming Bian , Yu-Ning Gao , Zhen-Jiang Liu
{"title":"Copper-catalyzed tandem cyclization reaction of ethynylbenzoxazinones and thiols: facile construction of 2-thiomethylene indoles†","authors":"Lei Song ,&nbsp;Fu-Qiang Li ,&nbsp;Xiao-Han Qiu ,&nbsp;Guo-Zhen Wei ,&nbsp;Hui-Yu Chen ,&nbsp;Ming Bian ,&nbsp;Yu-Ning Gao ,&nbsp;Zhen-Jiang Liu","doi":"10.1039/d4ob01164c","DOIUrl":null,"url":null,"abstract":"<div><div>The first successful copper-catalyzed decarboxylative cyclization reaction of ethynylbenzoxazinones and thiols has been developed. A rarely studied α-addition process to a copper–allenylidene intermediate promoted this reaction. Using this protocol, a range of 2-thiomethylene indole compounds have been obtained. This methodology offers significant advantages including mild reaction conditions, cheap catalysts, good yields and broad substrate compatibility.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 41","pages":"Pages 8268-8272"},"PeriodicalIF":2.7000,"publicationDate":"2024-09-16","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/S1477052024008334","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/18 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

The first successful copper-catalyzed decarboxylative cyclization reaction of ethynylbenzoxazinones and thiols has been developed. A rarely studied α-addition process to a copper–allenylidene intermediate promoted this reaction. Using this protocol, a range of 2-thiomethylene indole compounds have been obtained. This methodology offers significant advantages including mild reaction conditions, cheap catalysts, good yields and broad substrate compatibility.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
铜催化的乙炔基苯并恶嗪酮与硫醇的串联环化反应:2-硫代亚甲基吲哚的简易构建。
首次成功开发了铜催化的乙炔基苯并恶嗪酮与硫醇的脱羧环化反应。一个很少被研究的亚烯铜中间体α-加成过程促进了这一反应。利用这一方案,获得了一系列 2-硫亚甲基吲哚化合物。该方法具有反应条件温和、催化剂便宜、产率高和底物相容性广等显著优势。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
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.
期刊最新文献
A gold(III)-catalyzed Conia-ene reaction for the direct synthesis of substituted pyrroles from β-ketopropargyl amines. Aryne-involved α-C(sp3)-H arylation of 4-aminopyrazolones via two distinct systems: dual phase-transfer catalysis and ultraviolet photochemistry. Regio- and stereoselective ring-opening of aziridines: a click chemistry approach to chiral amino alcohols and triazole-modified compounds. Electricity-driven sustainable synthesis of 2-aminobenzonitriles through C-C bond cleavage of isatins: post-functionalization via one-pot integration with enzyme catalysis. Base-promoted cascade haloamination/β-elimination of alkenyl thianthrenium salts: access to (Z)-β-chloroenamines.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1