二烯催化环化法制备炔腙基3,5-二取代吡唑。

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC
Zhouting Zeng,Feng Zhao,Huimei Zhong,Zi Yang,Huaixin Wei,Songwen Ji,Mingming Yu,Jinhui Cai
{"title":"二烯催化环化法制备炔腙基3,5-二取代吡唑。","authors":"Zhouting Zeng,Feng Zhao,Huimei Zhong,Zi Yang,Huaixin Wei,Songwen Ji,Mingming Yu,Jinhui Cai","doi":"10.1021/acs.joc.5c02108","DOIUrl":null,"url":null,"abstract":"Given the existing limitations of traditional methods for the synthesis of pyrazole derivatives, developing new, mild, and efficient approach toward pyrazole skeletons is necessary. Herein, we report an electrochemically driven diselenide-catalyzed cyclization of 1,3-disubstituted prop-2-yn-1-one hydrazones that realize the rapid synthesis of 3,5-disubstituted pyrazoles under metal-free, oxidant-free, and base-free conditions. The practical utility of this method is underscored by its wide substrate scope, high tolerance toward various functional groups, high efficiency, mild conditions, gram-scale synthesis, and diverse derivatizations. Furthermore, the preliminary mechanistic experiments indicate that this reaction possibly proceeds via a cationic pathway.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"95 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Electrochemical Synthesis of 3,5-Disubstituted Pyrazoles from Ynone Hydrazones via Diselenide-Catalyzed Cyclization Strategy.\",\"authors\":\"Zhouting Zeng,Feng Zhao,Huimei Zhong,Zi Yang,Huaixin Wei,Songwen Ji,Mingming Yu,Jinhui Cai\",\"doi\":\"10.1021/acs.joc.5c02108\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Given the existing limitations of traditional methods for the synthesis of pyrazole derivatives, developing new, mild, and efficient approach toward pyrazole skeletons is necessary. Herein, we report an electrochemically driven diselenide-catalyzed cyclization of 1,3-disubstituted prop-2-yn-1-one hydrazones that realize the rapid synthesis of 3,5-disubstituted pyrazoles under metal-free, oxidant-free, and base-free conditions. The practical utility of this method is underscored by its wide substrate scope, high tolerance toward various functional groups, high efficiency, mild conditions, gram-scale synthesis, and diverse derivatizations. Furthermore, the preliminary mechanistic experiments indicate that this reaction possibly proceeds via a cationic pathway.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"95 1\",\"pages\":\"\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-10-20\",\"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://doi.org/10.1021/acs.joc.5c02108\",\"RegionNum\":2,\"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":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c02108","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

摘要

鉴于传统的吡唑衍生物合成方法存在的局限性,开发新的、温和的、高效的吡唑骨架合成方法是必要的。在此,我们报道了一种电化学驱动的二硒催化1,3-二取代-2-炔-1-酮腙的环化反应,实现了在无金属、无氧化剂和无碱条件下快速合成3,5-二取代吡唑。该方法具有底物范围广、对各种官能团耐受性强、效率高、条件温和、克级合成和多种衍生化等特点。此外,初步的机理实验表明,该反应可能通过阳离子途径进行。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Electrochemical Synthesis of 3,5-Disubstituted Pyrazoles from Ynone Hydrazones via Diselenide-Catalyzed Cyclization Strategy.
Given the existing limitations of traditional methods for the synthesis of pyrazole derivatives, developing new, mild, and efficient approach toward pyrazole skeletons is necessary. Herein, we report an electrochemically driven diselenide-catalyzed cyclization of 1,3-disubstituted prop-2-yn-1-one hydrazones that realize the rapid synthesis of 3,5-disubstituted pyrazoles under metal-free, oxidant-free, and base-free conditions. The practical utility of this method is underscored by its wide substrate scope, high tolerance toward various functional groups, high efficiency, mild conditions, gram-scale synthesis, and diverse derivatizations. Furthermore, the preliminary mechanistic experiments indicate that this reaction possibly proceeds via a cationic pathway.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
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.
×
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
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
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 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信