Visible‐light‐Mediated Dual Catalytic Spiro Annulation of 2‐Aryl Quinazolin‐4(3H)‐ones with N‐Substituted Maleimides

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC
Amol B. Kirwale, Rajesh T. Bhawale, Umesh A. Kshirsagar
{"title":"Visible‐light‐Mediated Dual Catalytic Spiro Annulation of 2‐Aryl Quinazolin‐4(3H)‐ones with N‐Substituted Maleimides","authors":"Amol B. Kirwale, Rajesh T. Bhawale, Umesh A. Kshirsagar","doi":"10.1002/ejoc.202500462","DOIUrl":null,"url":null,"abstract":"Visible light‐induced, dehydrogenative spiro annulation of 2‐aryl quinazolin‐4(3H)‐ones with maleimides has been achieved at ambient condition by merging Rh(III)‐catalysis with photo‐redox catalysis. Various spiro‐cyclized quinazolinone derivatives were synthesised with a broad substrate scope in up to 92% yields at room temperature. A further mechanistic study involving control experiments, UV spectroscopy, light on‐off experiments, kinetic isotope effect (KIE) study, H/D labelling study, and hydrogen peroxide detection tests has been explored. The present methodology was demonstrated to be effective for scale‐up synthesis, enabling the efficient generation of the spirocyclic product.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":2.5000,"publicationDate":"2025-06-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/ejoc.202500462","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

Visible light‐induced, dehydrogenative spiro annulation of 2‐aryl quinazolin‐4(3H)‐ones with maleimides has been achieved at ambient condition by merging Rh(III)‐catalysis with photo‐redox catalysis. Various spiro‐cyclized quinazolinone derivatives were synthesised with a broad substrate scope in up to 92% yields at room temperature. A further mechanistic study involving control experiments, UV spectroscopy, light on‐off experiments, kinetic isotope effect (KIE) study, H/D labelling study, and hydrogen peroxide detection tests has been explored. The present methodology was demonstrated to be effective for scale‐up synthesis, enabling the efficient generation of the spirocyclic product.
可见光介导的2 -芳基喹唑啉- 4(3H) -酮与N -取代马来酰亚胺的双催化螺旋环反应
在室温条件下,通过Rh(III)催化和光氧化还原催化的合并,实现了2芳基喹唑啉- 4(3H) -酮与马来酰亚胺在可见光诱导下的脱氢螺旋环反应。在室温条件下,合成了多种螺旋环化喹唑啉酮衍生物,底物范围广,产率高达92%。进一步的机理研究包括对照实验、紫外光谱、光开关实验、动力学同位素效应(KIE)研究、H/D标记研究和过氧化氢检测测试。本方法被证明是有效的大规模合成,使螺旋环产品的高效生成。
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 求助全文
来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
×
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