• 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

在无溶剂条件下,通过FeF₃催化的Pechmann缩合反应,微波辅助便捷一锅法合成香豆素衍生物及其产物的抗菌活性。

Microwave assisted convenient one-pot synthesis of coumarin derivatives via Pechmann condensation catalyzed by FeF3 under solvent-free conditions and antimicrobial activities of the products.

作者信息

Vahabi Vahid, Hatamjafari Farhad

机构信息

Department of Chemistry, Faculty of Science, Islamic Azad University-Tonekabon Branch, Tonekabon 46841-61167, Iran.

出版信息

Molecules. 2014 Aug 26;19(9):13093-103. doi: 10.3390/molecules190913093.

DOI:10.3390/molecules190913093
PMID:25255747
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6271414/
Abstract

A rapid and efficient solvent-free one-pot synthesis of coumarin derivatives by Pechmann condensation reactions of phenols with ethyl acetoacetate using FeF3 as a catalyst under microwave irradiation is described. This one-pot synthesis on a solid inorganic support provides the products in good yields. The newly synthesized compounds were systematically characterized by IR, 1H-NMR, 13C-NMR, MS and elemental CHN analyses. The proposed solvent-free microwave irradiation method using the environmentally friendly catalyst FeF3 offers the unique advantages of high yields, shorter reaction times, easy and quick isolation of the products, excellent chemoselectivity, and a one-pot, green synthesis. The products were screened for antimicrobial activity, and the results showed that the compounds reacted against all the tested bacteria.

摘要

描述了一种在微波辐射下,以FeF₃为催化剂,通过酚类与乙酰乙酸乙酯的Pechmann缩合反应快速高效地无溶剂一锅法合成香豆素衍生物。在固体无机载体上的这种一锅法合成以良好的产率提供产物。通过红外光谱、¹H-核磁共振、¹³C-核磁共振、质谱和元素CHN分析对新合成的化合物进行了系统表征。所提出的使用环境友好型催化剂FeF₃的无溶剂微波辐射方法具有产率高、反应时间短、产物分离容易快速、化学选择性优异以及一锅法绿色合成等独特优势。对产物进行了抗菌活性筛选,结果表明这些化合物对所有测试细菌均有反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/b50591d39e3a/molecules-19-13093-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/b5f1c463f4d9/molecules-19-13093-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/3a38a08157ba/molecules-19-13093-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/92d0dbb8e18f/molecules-19-13093-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/28ccd8c94718/molecules-19-13093-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/b50591d39e3a/molecules-19-13093-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/b5f1c463f4d9/molecules-19-13093-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/3a38a08157ba/molecules-19-13093-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/92d0dbb8e18f/molecules-19-13093-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/28ccd8c94718/molecules-19-13093-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec3e/6271414/b50591d39e3a/molecules-19-13093-g004.jpg

相似文献

1
Microwave assisted convenient one-pot synthesis of coumarin derivatives via Pechmann condensation catalyzed by FeF3 under solvent-free conditions and antimicrobial activities of the products.在无溶剂条件下,通过FeF₃催化的Pechmann缩合反应,微波辅助便捷一锅法合成香豆素衍生物及其产物的抗菌活性。
Molecules. 2014 Aug 26;19(9):13093-103. doi: 10.3390/molecules190913093.
2
Coumarin Derivatives Solvent-Free Synthesis under Microwave Irradiation over Heterogeneous Solid Catalysts.香豆素衍生物在多相固体催化剂微波辐射下无溶剂合成。
Molecules. 2017 Nov 28;22(12):2072. doi: 10.3390/molecules22122072.
3
FeCl3-catalysed ultrasonic-assisted, solvent-free synthesis of 4-substituted coumarins. A useful complement to the Pechmann reaction.三氯化铁催化的超声辅助无溶剂合成4-取代香豆素。佩希曼反应的有益补充。
Ultrason Sonochem. 2014 May;21(3):937-42. doi: 10.1016/j.ultsonch.2013.10.018. Epub 2013 Oct 29.
4
FeO@C@OSOH as an efficient, recyclable magnetic nanocatalyst in Pechmann condensation: green synthesis, characterization, and theoretical study.FeO@C@OSOH 作为一种高效、可回收的磁性纳米催化剂在 Pechmann 缩合反应中的应用:绿色合成、表征和理论研究。
Mol Divers. 2021 Feb;25(1):67-86. doi: 10.1007/s11030-019-10025-w. Epub 2020 Jan 11.
5
FeF-mediated tandem annulation: a highly efficient one-pot synthesis of functionalized N-methyl-3-nitro-4H-pyrimido [2, 1-b] [1, 3] benzothiazole-2-amine derivatives under neat conditions.FeF 介导的串联环化反应:在无溶剂条件下高效一锅合成功能化的 N-甲基-3-硝基-4H-嘧啶并[2,1-b][1,3]苯并噻唑-2-胺衍生物。
Mol Divers. 2020 May;24(2):443-453. doi: 10.1007/s11030-019-09963-2. Epub 2019 May 29.
6
Green Synthesis of Fused Chromeno-pyrazolo-phthalazine Derivatives with Silicasupported Bismuth Nitrate under Solvent-free Conditions.无溶剂条件下硅胶负载硝酸铋催化合成稠合色烯并吡唑并酞嗪衍生物的绿色合成法
Curr Org Synth. 2021;18(8):854-861. doi: 10.2174/1570179417666201208112520.
7
Greener Syntheses of Coumarin Derivatives Using Magnetic Nanocatalysts: Recent Advances.使用磁性纳米催化剂的香豆素衍生物的绿色合成:最新进展
Top Curr Chem (Cham). 2022 Nov 12;381(1):1. doi: 10.1007/s41061-022-00407-4.
8
Recyclable Keggin Heteropolyacids as an Environmentally Benign Catalyst for the Synthesis of New 2-Benzoylamino-N-phenyl-benzamide Derivatives under Microwave Irradiations at Solvent-Free Conditions and the Evaluation of Biological Activity.可回收的 Keggin 杂多酸作为一种环境友好的催化剂,在无溶剂条件下微波辐射下用于新型 2-苯甲酰胺基-N-苯基苯甲酰胺衍生物的合成,并评价了其生物活性。
Molecules. 2017 Dec 21;23(1):8. doi: 10.3390/molecules23010008.
9
Microwave assisted synthesis and determination of in-vitro antimicrobial efficacy of well characterized s-triazinyl piperazines and piperidines.微波辅助合成及表征良好的均三嗪基哌嗪和哌啶的体外抗菌效果测定
Acta Pol Pharm. 2012 May-Jun;69(3):423-32.
10
Microwave assisted, one-pot synthesis of 5-nitro- 2-aryl substituted-1H-benzimidazole libraries: screening in vitro for antimicrobial activity.微波辅助一锅法合成 5-硝基-2-芳基取代-1H-苯并咪唑库:体外筛选抗菌活性。
J Enzyme Inhib Med Chem. 2009 Oct;24(5):1095-100. doi: 10.1080/14756360802632716.

引用本文的文献

1
Carbon nanofiber/taurine-catalyzed synthesis of coumarin and 1,2,4,5-tetra-substituted imidazole derivatives under metal-free conditions.碳纳米纤维/牛磺酸催化在无金属条件下合成香豆素和1,2,4,5-四取代咪唑衍生物
Sci Rep. 2024 May 9;14(1):10677. doi: 10.1038/s41598-024-61249-2.
2
A review on convenient synthesis of substituted coumarins using reuseable solid acid catalysts.关于使用可重复使用的固体酸催化剂方便合成取代香豆素的综述。
RSC Adv. 2021 Sep 1;11(47):29130-29155. doi: 10.1039/d1ra04887b.
3
Coumarin Derivatives Solvent-Free Synthesis under Microwave Irradiation over Heterogeneous Solid Catalysts.

本文引用的文献

1
Analysis, isolation and insecticidal activity of linear furanocoumarins and other coumarin derivatives fromPeucedanum (Apiaceae: Apioideae).从Peucedanum(伞形科:Apioideae)中分析、分离线性呋喃香豆素和其他香豆素衍生物及其杀虫活性。
J Chem Ecol. 1994 Aug;20(8):2035-54. doi: 10.1007/BF02066241.
2
Antifungal activities of new coumarins.新型香豆素的抗真菌活性。
Molecules. 2012 May 14;17(5):5713-23. doi: 10.3390/molecules17055713.
3
Synthesis and properties of fluorescence dyes: tetracyclic pyrazolo[3,4-b]pyridine-based coumarin chromophores with intramolecular charge transfer character.
香豆素衍生物在多相固体催化剂微波辐射下无溶剂合成。
Molecules. 2017 Nov 28;22(12):2072. doi: 10.3390/molecules22122072.
4
Zirconia-based catalyst for the one-pot synthesis of coumarin through Pechmann reaction.用于通过Pechmann反应一锅合成香豆素的氧化锆基催化剂。
Nanoscale Res Lett. 2016 Dec;11(1):345. doi: 10.1186/s11671-016-1525-3. Epub 2016 Jul 26.
荧光染料的合成与性质:具有分子内电荷转移特性的基于四环吡唑并[3,4-b]吡啶的香豆素发色团。
J Org Chem. 2012 Apr 6;77(7):3475-82. doi: 10.1021/jo3002722. Epub 2012 Mar 27.
4
Developmental effects of coumarin and the anticoagulant coumarin derivative warfarin on zebrafish (Danio rerio) embryos.香豆素和抗凝血香豆素衍生物华法林对斑马鱼(Danio rerio)胚胎的发育影响。
Reprod Toxicol. 2012 Apr;33(2):133-41. doi: 10.1016/j.reprotox.2011.07.001. Epub 2011 Jul 21.
5
Synthetic and natural coumarins as cytotoxic agents.合成与天然香豆素作为细胞毒性剂
Curr Med Chem Anticancer Agents. 2005 Jan;5(1):29-46. doi: 10.2174/1568011053352550.
6
A novel and efficient methodology for the C-C bond forming radical cyclization of hydrophobic substrates in water.一种用于在水中进行疏水底物的碳-碳键形成自由基环化反应的新颖且高效的方法。
Org Lett. 2001 Apr 19;3(8):1157-60. doi: 10.1021/ol010014p.
7
Coumarin metabolism, toxicity and carcinogenicity: relevance for human risk assessment.香豆素的代谢、毒性与致癌性:对人类风险评估的意义
Food Chem Toxicol. 1999 Apr;37(4):423-53. doi: 10.1016/s0278-6915(99)00010-1.