通过 Cu(II)-Catalyzed Amination 和 N-氧化物与邻烷基苯胺之间的腈化反应合成喹啉-吲哚杂化物

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC
Amitava Rakshit, Kyeongwon Moon, Pargat Singh, Jung Su Park, In Su Kim
{"title":"通过 Cu(II)-Catalyzed Amination 和 N-氧化物与邻烷基苯胺之间的腈化反应合成喹啉-吲哚杂化物","authors":"Amitava Rakshit, Kyeongwon Moon, Pargat Singh, Jung Su Park, In Su Kim","doi":"10.1021/acs.orglett.4c04375","DOIUrl":null,"url":null,"abstract":"The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline <i>N</i>-oxides with <i>o</i>-alkynylanilines in the presence of a combination of copper(II) catalyst and a bidentate 2,2′-bipyridine ligand is described. The utility of this method was demonstrated through site-selective functionalization of the synthesized products. A plausible reaction pathway for site-selective amination followed by annulative indole formation was elucidated by a series of mechanistic investigations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of Quinoline–Indole Hybrids through Cu(II)-Catalyzed Amination and Annulation between N-Oxides and o-Alkynylanilines\",\"authors\":\"Amitava Rakshit, Kyeongwon Moon, Pargat Singh, Jung Su Park, In Su Kim\",\"doi\":\"10.1021/acs.orglett.4c04375\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline <i>N</i>-oxides with <i>o</i>-alkynylanilines in the presence of a combination of copper(II) catalyst and a bidentate 2,2′-bipyridine ligand is described. The utility of this method was demonstrated through site-selective functionalization of the synthesized products. A plausible reaction pathway for site-selective amination followed by annulative indole formation was elucidated by a series of mechanistic investigations.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"32 1\",\"pages\":\"\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-12-16\",\"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.4c04375\",\"RegionNum\":1,\"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 Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04375","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

摘要

本文介绍了在铜(II)催化剂和双齿 2,2′-联吡啶配体的共同作用下,通过(异)喹啉 N-氧化物与邻炔基苯胺反应合成(异)喹啉-吲哚杂化物的方法。通过对合成产物进行位点选择性官能化,证明了这种方法的实用性。通过一系列机理研究,阐明了位点选择性胺化然后形成环状吲哚的合理反应途径。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Synthesis of Quinoline–Indole Hybrids through Cu(II)-Catalyzed Amination and Annulation between N-Oxides and o-Alkynylanilines

Synthesis of Quinoline–Indole Hybrids through Cu(II)-Catalyzed Amination and Annulation between N-Oxides and o-Alkynylanilines
The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline N-oxides with o-alkynylanilines in the presence of a combination of copper(II) catalyst and a bidentate 2,2′-bipyridine ligand is described. The utility of this method was demonstrated through site-selective functionalization of the synthesized products. A plausible reaction pathway for site-selective amination followed by annulative indole formation was elucidated by a series of mechanistic investigations.
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
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.
×
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:481959085
Book学术官方微信