Synthesis of spiro-1,2-dihydropyridine derivatives via cycloisomerization of 3-aza-1,5-enynes catalyzed by gold(I) complex/polyoxometalate hybrids.

IF 2.7 4区 化学 Q2 CHEMISTRY, ORGANIC
Beilstein Journal of Organic Chemistry Pub Date : 2026-09-28 eCollection Date: 2026-01-01 DOI:10.3762/bjoc.22.106
Titien Simon, Fabian Schlimpen, Pierre de Frémont, Stefan Chassaing, Aurélien Blanc
{"title":"Synthesis of spiro-1,2-dihydropyridine derivatives via cycloisomerization of 3-aza-1,5-enynes catalyzed by gold(I) complex/polyoxometalate hybrids.","authors":"Titien Simon, Fabian Schlimpen, Pierre de Frémont, Stefan Chassaing, Aurélien Blanc","doi":"10.3762/bjoc.22.106","DOIUrl":null,"url":null,"abstract":"<p><p>This study reports an optimized method for the synthesis of spiro-1,2-dihydropyridines via the cycloisomerization of 3-aza-1,5-enynes, catalyzed by heterogeneous gold(I)-polyoxometalate (POM) hybrids. By replacing traditional homogeneous catalysts with these hybrid systems, we achieved high yields (up to 82% isolated) in short reaction times, while minimizing product degradation. The reaction scope was demonstrated across a broad range of substrates, including aryl, alkyl, and heterocyclic derivatives, as well as variations in ring size and nitrogen substituents using 5 mol % of [Au<sup>I</sup>(IPr)(MeCN)][H<sub>5</sub>P<sub>2</sub>W<sub>18</sub>O<sub>64</sub>] as catalyst.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 ","pages":"1316-1322"},"PeriodicalIF":2.7000,"publicationDate":"2026-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13635902/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.22.106","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2026/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

This study reports an optimized method for the synthesis of spiro-1,2-dihydropyridines via the cycloisomerization of 3-aza-1,5-enynes, catalyzed by heterogeneous gold(I)-polyoxometalate (POM) hybrids. By replacing traditional homogeneous catalysts with these hybrid systems, we achieved high yields (up to 82% isolated) in short reaction times, while minimizing product degradation. The reaction scope was demonstrated across a broad range of substrates, including aryl, alkyl, and heterocyclic derivatives, as well as variations in ring size and nitrogen substituents using 5 mol % of [AuI(IPr)(MeCN)][H5P2W18O64] as catalyst.

金(I)配合物/多金属氧酸盐杂化催化3-叠氮-1,5-烯环异构化合成螺-1,2-二氢吡啶衍生物。
本研究报道了在非均相金(I)-多金属氧酸(POM)杂化物催化下,通过3-叠氮-1,5-烯的环异构化反应合成螺-1,2-二氢吡啶的优化方法。通过用这些混合系统取代传统的均相催化剂,我们在短反应时间内实现了高收率(分离率高达82%),同时最大限度地减少了产品降解。在5mol %的[AuI(IPr)(MeCN)][H5P2W18O64]催化剂的催化下,反应范围包括芳基、烷基和杂环衍生物,以及环尺寸和氮取代基的变化。
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
4.90
自引率
3.70%
发文量
167
审稿时长
1.4 months
期刊介绍: The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
×
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
小红书