Palladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-c]quinolines

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2024-12-10 DOI:10.1021/acs.joc.4c02142
Qiushan Gao, Binbin Wang, Huanfeng Jiang, Wanqing Wu
{"title":"Palladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-c]quinolines","authors":"Qiushan Gao, Binbin Wang, Huanfeng Jiang, Wanqing Wu","doi":"10.1021/acs.joc.4c02142","DOIUrl":null,"url":null,"abstract":"A novel strategy for the synthesis of various isochromeno[4,3-<i>c</i>]quinolines via palladium-catalyzed tandem cyclization of functional diarylalkynes with isocyanides has been developed. This approach features excellent chemo- and regioselectivities as well as good functional group tolerance. Notably, 6-phenylimino-6<i>H</i>-isochromeno[4,3-<i>c</i>]quinolin-11-amines and 11-amino-6<i>H</i>-isochromeno[4,3-<i>c</i>]quinolin-6-ones can be selectively constructed by employing different protecting groups of functional diarylalkynes. The gram-scale and late-stage modifications further demonstrate the synthetic value of this method.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"95 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2024-12-10","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.4c02142","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

A novel strategy for the synthesis of various isochromeno[4,3-c]quinolines via palladium-catalyzed tandem cyclization of functional diarylalkynes with isocyanides has been developed. This approach features excellent chemo- and regioselectivities as well as good functional group tolerance. Notably, 6-phenylimino-6H-isochromeno[4,3-c]quinolin-11-amines and 11-amino-6H-isochromeno[4,3-c]quinolin-6-ones can be selectively constructed by employing different protecting groups of functional diarylalkynes. The gram-scale and late-stage modifications further demonstrate the synthetic value of this method.

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
钯催化功能性二芳基炔和异氰酸酯的串联环化以组装异色烯并[4,3-c]喹啉类化合物
提出了一种钯催化二芳基醚与异氰酸酯串联环化合成多种等色[4,3-c]喹啉的新方法。这种方法具有优异的化学和区域选择性以及良好的功能基团耐受性。值得注意的是,6-苯基氨基- 6h -等色[4,3-c]喹啉-11-胺和11-氨基- 6h -等色[4,3-c]喹啉-6-酮可以通过使用不同的功能二芳炔保护基团选择性地构建。克尺度和后期修正进一步证明了该方法的综合价值。
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
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.
期刊最新文献
Visible-Light-Mediated Multicomponent Synthesis of Azido-Substituted gem-Difluoroalkenes. Organocatalytic Synthesis of Amides Using Thioacids and Anilines via Electron Donor-Acceptor Photoactivation. Synthesis of Dideuterofluoroarene 3ΔF(D)-NMR Reporter-Resolvers for Structural, Mechanistic, and Kinetic Studies Cu/Zn-Catalyzed Synthesis of ε-Keto Sulfones from Cyclopropanols Ryanodane Diterpenoids from Cinnamon and Their Analgesic and Hepatoprotective Effects
×
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