• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

离子液体绿色介质中膦介导的α-肟基酮与二烷基乙炔二羧酸酯合成2,3,4,5-四取代N-羟基吡咯

A Phosphine-mediated Synthesis of 2,3,4,5-tetra-substituted N-hydroxypyrroles from α-oximino Ketones and Dialkyl Acetylenedicarboxylates Under Ionic Liquid Green-media.

作者信息

Shahvelayati Ashraf S, Ghazvini Maryam, Yadollahzadeh Khadijeh, Delbari Akram S

机构信息

Department of Chemistry, Yadegar-e-Imam Khomeini (RAH) Shahre-rey Branch, Islamic Azad University, Tehran, Iran.

Department of Chemistry, Payame Noor University, P.O. Box, 19395-4697, Tehran, Iran.

出版信息

Comb Chem High Throughput Screen. 2018;21(1):14-18. doi: 10.2174/1386207321666180124094536.

DOI:10.2174/1386207321666180124094536
PMID:29366409
Abstract

BACKGROUND

The development of multicomponent reactions (MCRs) in the presence of task-specific ionic liquids (ILs), used not only as environmentally benign reaction media, but also as catalysts, is a new approach that meet with the requirements of sustainable chemistry. In recent years, the use of ionic liquids as a green media for organic synthesis has become a chief study area. This is due to their unique properties such as non-volatility, non-flammability, chemical and thermal stability, immiscibility with both organic compounds and water and recyclability. Ionic liquids are used as environmentally friendly solvents instead of hazardous organic solvents.

OBJECTIVE

We report the condensation reaction between α-oximinoketone and dialkyl acetylene dicarboxylate in the presence of triphenylphosphine to afford substituted pyrroles under ionic liquid conditions in good yields.

RESULT

Densely functionalized pyrroles was easily prepared from reaction of α-oximinoketones, dialkyl acetylene dicarboxylate in the presence of triphenylphosphine in a quantitative yield under ionic liquid conditions at room temperature.

CONCLUSION

In conclusion, ionic liquids are indicated as a useful and novel reaction medium for the selective synthesis of functionalized pyrroles. This reaction medium can replace the use of hazardous organic solvents. Easy work-up, synthesis of polyfunctional compounds, decreased reaction time, having easily available-recyclable ionic liquids, and good to high yields are advantages of present method.

摘要

背景

在特定任务离子液体(ILs)存在下进行多组分反应(MCRs)的发展,离子液体不仅用作环境友好的反应介质,还用作催化剂,是一种符合可持续化学要求的新方法。近年来,将离子液体用作有机合成的绿色介质已成为主要研究领域。这是由于它们具有诸如不挥发性、不可燃性、化学和热稳定性、与有机化合物和水均不混溶以及可回收性等独特性质。离子液体被用作环境友好型溶剂以替代有害的有机溶剂。

目的

我们报道了在离子液体条件下,α-肟基酮与二烷基乙炔二羧酸酯在三苯基膦存在下发生缩合反应,以良好产率得到取代吡咯。

结果

在离子液体条件下,于室温下,α-肟基酮、二烷基乙炔二羧酸酯在三苯基膦存在下反应,能以定量产率轻松制备出功能化密集的吡咯。

结论

总之,离子液体被证明是用于选择性合成功能化吡咯的一种有用且新颖的反应介质。这种反应介质可替代有害有机溶剂的使用。后处理简便、多官能团化合物的合成、反应时间缩短、离子液体易于获得且可回收以及产率良好至高是本方法的优点。

相似文献

1
A Phosphine-mediated Synthesis of 2,3,4,5-tetra-substituted N-hydroxypyrroles from α-oximino Ketones and Dialkyl Acetylenedicarboxylates Under Ionic Liquid Green-media.离子液体绿色介质中膦介导的α-肟基酮与二烷基乙炔二羧酸酯合成2,3,4,5-四取代N-羟基吡咯
Comb Chem High Throughput Screen. 2018;21(1):14-18. doi: 10.2174/1386207321666180124094536.
2
Efficient and green synthesis of tetrasubstituted pyrroles promoted by task-specific basic ionic liquids as catalyst in aqueous media.在水相介质中,以功能化离子液体作为催化剂促进四取代吡咯的高效绿色合成。
Mol Divers. 2009 Nov;13(4):519-28. doi: 10.1007/s11030-009-9146-8. Epub 2009 Apr 21.
3
Chemoselective allylation of ketones in ionic liquids containing sulfonate anions.含磺酸根阴离子的离子液体中酮的化学选择性烯丙基化反应。
ChemSusChem. 2009;2(11):1045-50. doi: 10.1002/cssc.200900198.
4
Ionic Liquid-assisted Preparation of Two-dimensional ZnO/Fe3O4 Nano-composites and their Application in Polysubstituted Pyrroles Synthesis.离子液体辅助制备二维ZnO/Fe₃O₄纳米复合材料及其在多取代吡咯合成中的应用。
Comb Chem High Throughput Screen. 2020;23(1):55-65. doi: 10.2174/1386207323666200107100148.
5
Room Temperature Ionic Liquids as Green Solvent Alternatives in the Metathesis of Oleochemical Feedstocks.室温离子液体作为油脂化学原料复分解反应中绿色溶剂的替代品
Molecules. 2016 Feb 6;21(2):184. doi: 10.3390/molecules21020184.
6
Copper- or phosphine-catalyzed reaction of alkynes with isocyanides. Regioselective synthesis of substituted pyrroles controlled by the catalyst.铜或膦催化的炔烃与异腈的反应。由催化剂控制的取代吡咯的区域选择性合成。
J Am Chem Soc. 2005 Jun 29;127(25):9260-6. doi: 10.1021/ja051875m.
7
Metal-free, ionic liquid-mediated synthesis of functionalized quinolines.无金属、离子液体介导的功能化喹啉的合成。
ACS Comb Sci. 2014 Nov 10;16(11):624-30. doi: 10.1021/co500047w. Epub 2014 Oct 21.
8
A fast and highly efficient protocol for synthesis of pyrrolo[2,3-d]isoxazoles and a new series of novel benzyl bis-pyrrolo[2,3-d]isoxazoles using task-specific ionic liquids as catalyst and green solvent.一种使用特定任务离子液体作为催化剂和绿色溶剂合成吡咯并[2,3 - d]异恶唑以及一系列新型苄基双吡咯并[2,3 - d]异恶唑的快速且高效的方法。
Chem Pharm Bull (Tokyo). 2010 Jun;58(6):833-9. doi: 10.1248/cpb.58.833.
9
An efficient synthesis of quinolines derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation via the tandem addition/annulation reaction of o-aminoaryl ketones with alpha-methylene ketones.在室温离子液体促进下,于环境条件下通过超声辐射,使邻氨基芳基酮与α-亚甲基酮发生串联加成/环化反应,高效合成喹啉衍生物。
Ultrason Sonochem. 2009 Mar;16(3):361-6. doi: 10.1016/j.ultsonch.2008.11.001. Epub 2008 Nov 9.
10
Acidic-functionalized ionic liquid as an efficient, green and reusable catalyst for hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to α,β-unsaturated ketones.酸性功能化离子液体作为高效、绿色、可重复使用的催化剂,用于氮、硫和氧亲核试剂与α,β-不饱和酮的杂迈克尔加成反应。
Org Biomol Chem. 2012 Jan 14;10(2):346-54. doi: 10.1039/c1ob06346d. Epub 2011 Nov 11.