Electrochemical Synthesis of 3-(Sulfonyl)quinol-4-ones from o-Alkynyl-N-(formyl)anilides and Sulfinates

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-25 DOI:10.1021/acs.orglett.4c04209
Vladimir L. Bondarev, Alexey A. Festa, Olga A. Storozhenko, Vladimir A. Kokorekin, Anton P. Novikov, Alexey V. Varlamov, Leonid G. Voskressensky
{"title":"Electrochemical Synthesis of 3-(Sulfonyl)quinol-4-ones from o-Alkynyl-N-(formyl)anilides and Sulfinates","authors":"Vladimir L. Bondarev, Alexey A. Festa, Olga A. Storozhenko, Vladimir A. Kokorekin, Anton P. Novikov, Alexey V. Varlamov, Leonid G. Voskressensky","doi":"10.1021/acs.orglett.4c04209","DOIUrl":null,"url":null,"abstract":"Electrolysis of <i>o</i>-alkynyl-<i>N</i>-(formyl)anilides and sodium sulfinates on graphite electrodes delivers biologically sound 3-(sulfonyl)quinol-4-ones with moderate to good yields. The reaction is carried out in an undivided cell in the presence of silver(I) oxide with potassium iodide or sodium tetrafluoroborate as the supporting electrolyte. The reaction tolerates variously substituted anilides as well as aryl and alkyl sulfinates. The transformation proceeds as a domino sequence of oxysulfonylation and cyclocondensation steps.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"70 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-12-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04209","RegionNum":1,"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

Electrolysis of o-alkynyl-N-(formyl)anilides and sodium sulfinates on graphite electrodes delivers biologically sound 3-(sulfonyl)quinol-4-ones with moderate to good yields. The reaction is carried out in an undivided cell in the presence of silver(I) oxide with potassium iodide or sodium tetrafluoroborate as the supporting electrolyte. The reaction tolerates variously substituted anilides as well as aryl and alkyl sulfinates. The transformation proceeds as a domino sequence of oxysulfonylation and cyclocondensation steps.

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
邻炔基- n -(甲酰基)苯胺和亚硫酸盐电化学合成3-(磺酰基)喹啉-4-酮
在石墨电极上电解邻炔基- n -(甲酰基)苯胺和亚硫酸钠可获得生物无害的3-(磺酰基)喹啉-4-酮,收率中等至较高。该反应在氧化银(I)存在的未分裂电池中进行,碘化钾或四氟硼酸钠作为支持电解质。该反应可耐受各种取代苯胺以及芳基亚硫酸盐和烷基亚硫酸盐。转化作为一个多米诺骨牌序列的氧磺化和环缩合步骤进行。
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 Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
期刊最新文献
Issue Editorial Masthead Issue Publication Information Enantioselective Synthesis of Seven-Membered Bridged Biaryls via Pd-Catalyzed Asymmetric Annulative Allylic Alkylation Electrochemical Radical Addition-Initiated Ring-Opening/Functionalization of 2-Alkylidenecyclobutanols toward γ,δ-Unsaturated Ketone Synthesis Au(I)/Au(III)-Catalyzed Annulative Addition of Alkynes to Aryl Iodides
×
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