NHC-Catalyzed, Microwave-Assisted and Base-Dependent Reactions of Substituted Cinnamaldehydes Towards γ-Lactones or Saturated Esters

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-11-06 DOI:10.1002/ejoc.202401047
Victoria Magrioti, Evanthia Papadaki, Antonia Kapoti, Roza Leitourgaki, Aikaterini Vogiatzi
{"title":"NHC-Catalyzed, Microwave-Assisted and Base-Dependent Reactions of Substituted Cinnamaldehydes Towards γ-Lactones or Saturated Esters","authors":"Victoria Magrioti, Evanthia Papadaki, Antonia Kapoti, Roza Leitourgaki, Aikaterini Vogiatzi","doi":"10.1002/ejoc.202401047","DOIUrl":null,"url":null,"abstract":"N-Heterocyclic carbenes (NHCs) generated from imidazolium, imidazopyridinium and imidazoquinolinium hydrochlorides in situ using base and microwave irradiation were employed as organocatalysts to yield homoenolates from cinnamaldehyde and its aryl-substituted analogs. Depending on the catalytic base either γ-lactones were prepared when the strong base tBuOK was used or the corresponding saturated ethyl 3-aryl propionates were synthesized with the milder DIPEA base. Novel imidazopyridinium and imidazoquinolinium hydrochlorides were synthesized and were compared to commercially available NHCs IMes and IDip for their catalytic activity. The optimum reaction conditions were established using IMes and the broad scope of both reactions was investigated using the 4 most efficient NHCs.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.5000,"publicationDate":"2024-11-06","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.202401047","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

N-Heterocyclic carbenes (NHCs) generated from imidazolium, imidazopyridinium and imidazoquinolinium hydrochlorides in situ using base and microwave irradiation were employed as organocatalysts to yield homoenolates from cinnamaldehyde and its aryl-substituted analogs. Depending on the catalytic base either γ-lactones were prepared when the strong base tBuOK was used or the corresponding saturated ethyl 3-aryl propionates were synthesized with the milder DIPEA base. Novel imidazopyridinium and imidazoquinolinium hydrochlorides were synthesized and were compared to commercially available NHCs IMes and IDip for their catalytic activity. The optimum reaction conditions were established using IMes and the broad scope of both reactions was investigated using the 4 most efficient NHCs.
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
NHC 催化、微波辅助和碱依赖的取代肉桂醛与γ-内酯或饱和酯的反应
利用碱和微波辐照从咪唑鎓、咪唑吡啶鎓和咪唑喹啉鎓盐酸盐原位生成的 N-杂环碳烯(NHC)作为有机催化剂,从肉桂醛及其芳基取代的类似物中生成均烯醇酯。根据催化碱的不同,要么使用强碱 tBuOK 制备出 γ-内酯,要么使用较温和的 DIPEA 碱合成相应的饱和 3-芳基丙酸乙酯。合成了新型咪唑吡啶鎓和咪唑喹啉鎓盐酸盐,并与市售的 NHC IMes 和 IDip 进行了催化活性比较。使用 IMes 确定了最佳反应条件,并使用 4 种最有效的 NHC 研究了这两种反应的广泛范围。
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
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.
期刊最新文献
Chemical Synthesis of β‐(1,4)‐d‐Oligomannurarates with Purported Anti‐Alzheimer Activity Scandium‐Catalyzed Fischer Indole Synthesis: A Highly Efficient Construction of Complicated Indoles Front Cover: Methanol‐Mediated One‐Pot Transformation of Benzonitriles to Five and Six‐Membered Heterocycles: Synthesis and Mechanistic Approach (Eur. J. Org. Chem. 41/2024) Addition of Sydnones to para‐Quinone Methides: Selective 1,6‐Additions and Oxidative C−H Functionalizations Aryl Radicals Generated from Aryl Pinacol Boronates Modify Peptides and Proteins
×
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