Rh(iii)-catalyzed C–H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones†

Yubo Duan , Shu-Ning Lu , Zuguang Yang , Zhengkai Chen , Xiao-Feng Wu
{"title":"Rh(iii)-catalyzed C–H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones†","authors":"Yubo Duan ,&nbsp;Shu-Ning Lu ,&nbsp;Zuguang Yang ,&nbsp;Zhengkai Chen ,&nbsp;Xiao-Feng Wu","doi":"10.1039/d3qo00803g","DOIUrl":null,"url":null,"abstract":"<div><p>An efficient and straightforward strategy for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones <em>via</em> Rh(<span>iii</span>)-catalyzed C–H activation/annulation of <em>N</em>-carbamoylindoles with CF<sub>3</sub>-imidoyl sulfoxonium ylides has been achieved. The cascade reaction might proceed through a C–H imidoylmethylation, tautomerization and intramolecular nucleophilic addition sequence. A wide range of functionalized pyrimidoindolone derivatives were constructed in good to excellent yields under redox-neutral conditions.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 15","pages":"Pages 3843-3848"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052411023009380","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

Abstract

An efficient and straightforward strategy for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones via Rh(iii)-catalyzed C–H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides has been achieved. The cascade reaction might proceed through a C–H imidoylmethylation, tautomerization and intramolecular nucleophilic addition sequence. A wide range of functionalized pyrimidoindolone derivatives were constructed in good to excellent yields under redox-neutral conditions.

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
Rh(iii)催化的C-H活化/ n -氨基甲酰亚砜酰脲环化反应用于三氟甲基取代(二氢)嘧啶吲哚酮的发散合成
通过Rh(iii)催化的N-氨基甲酰基吲哚的C–H活化/环化与CF3酰亚磺酰亚磺酰基亚磺酰基化,实现了一种高效而直接的发散合成三氟甲基取代的(二氢)嘧啶吲哚酮的策略。级联反应可能通过C–H酰亚胺甲基化、互变异构化和分子内亲核加成序列进行。在氧化还原中性条件下,以良好至优异的产率构建了广泛的功能化嘧啶并吲哚酮衍生物。
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
CiteScore
7.80
自引率
0.00%
发文量
0
期刊最新文献
Synthesis of biologically active [1,5]diazocino[2,1-b]quinazolinones through [4 + 4] cycloaddition of 2-alkynyl quinazolinones with aza-ortho-quinone methides† Synthesis of fluorinated allylic alcohols via photoinduced decarboxylative cross-coupling of α-fluoroacrylic acids and alcohols† Aromatization-driven cascade [1,5]-hydride transfer/cyclization for synthesis of spirochromanes† Playing with the cavity size of exTTF-based self-assembled cages† An alternative approach to triazatruxene synthesis and derivatization to a boron difluoride complex†
×
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:481959085
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