• 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

铁(III)催化的 1,3-二羰基化合物、胺、醛和硝基烷烃的四组分偶联反应:功能化吡咯的简单直接合成方法。

Iron(III)-catalyzed four-component coupling reaction of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes: a simple and direct synthesis of functionalized pyrroles.

机构信息

Department of Chemistry, Jadavpur University, Kolkata 700032, West Bengal, India.

出版信息

J Org Chem. 2010 Mar 5;75(5):1674-83. doi: 10.1021/jo902661y.

DOI:10.1021/jo902661y
PMID:20131775
Abstract

A simple, convenient, and multicomponent coupling strategy for the synthesis of highly functionalized pyrroles catalyzed by iron(III) salts has been developed. This strategy demonstrated four-component coupling reactions of 1,3-dicarbonyl compounds, amines, aromatic aldehydes, and nitroalkanes without an inert atmosphere. This methodology provides an alternative approach for easy access of highly substituted pyrroles in moderate to very good yields using four simple and readily available building blocks via one-pot tandem reaction. Notably, this method is very cheap, straightforward, and environmentally friendly compared to the existing methods.

摘要

一种简单、方便、多组分的铁(III)盐催化合成高度官能化吡咯的方法已经被开发出来。该策略在无需惰性气氛的情况下,展示了 1,3-二羰基化合物、胺、芳醛和硝基烷烃的四组分偶联反应。该方法提供了一种替代方法,可通过一锅串联反应,以中等至非常好的收率,使用四个简单易得的构建块,轻松获得高取代吡咯。值得注意的是,与现有方法相比,该方法非常廉价、直接且环保。

相似文献

1
Iron(III)-catalyzed four-component coupling reaction of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes: a simple and direct synthesis of functionalized pyrroles.铁(III)催化的 1,3-二羰基化合物、胺、醛和硝基烷烃的四组分偶联反应:功能化吡咯的简单直接合成方法。
J Org Chem. 2010 Mar 5;75(5):1674-83. doi: 10.1021/jo902661y.
2
One-pot three-component catalytic synthesis of fully substituted pyrroles from readily available propargylic alcohols, 1,3-dicarbonyl compounds and primary amines.由易得的炔丙醇、1,3 - 二羰基化合物和伯胺一锅法三组分催化合成全取代吡咯。
Chemistry. 2007;13(35):9973-81. doi: 10.1002/chem.200701132.
3
Iron(III)-catalyzed and air-mediated tandem reaction of aldehydes, alkynes and amines: an efficient approach to substituted quinolines.铁(III)催化及空气介导的醛、炔烃和胺的串联反应:一种合成取代喹啉的有效方法。
Chemistry. 2009 Jun 22;15(26):6332-4. doi: 10.1002/chem.200900875.
4
One-pot highly efficient synthesis of substituted pyrroles and N-bridgehead pyrroles by zinc-catalyzed multicomponent reaction.一锅法锌催化多组分反应高效合成取代吡咯和 N-桥连吡咯。
Org Biomol Chem. 2010 Jun 28;8(13):3064-72. doi: 10.1039/c003885g. Epub 2010 May 18.
5
L-proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines.L-脯氨酸催化合成高官能化多取代 1,4-二氢吡啶。
Org Biomol Chem. 2009 Dec 7;7(23):4943-53. doi: 10.1039/b914659h. Epub 2009 Oct 5.
6
Palladium-catalyzed carbonylative cross-coupling with imines: a multicomponent synthesis of imidazolones.钯催化的与亚胺的羰基化交叉偶联:咪唑酮的多组分合成
J Org Chem. 2008 Feb 1;73(3):1135-8. doi: 10.1021/jo701875b. Epub 2007 Dec 29.
7
A simple and efficient route to N-functionalized dithieno[3,2-b:2',3'-d]pyrroles: fused-ring building blocks for new conjugated polymeric systems.一种通往N-官能化二噻吩并[3,2-b:2',3'-d]吡咯的简单高效路线:用于新型共轭聚合物体系的稠环结构单元。
J Org Chem. 2003 Apr 4;68(7):2921-8. doi: 10.1021/jo034078k.
8
Iron-catalyzed synthesis of polysubstituted pyrroles via [4C+1N] cyclization of 4-acetylenic ketones with primary amines.铁催化的 4-炔基酮与伯胺的[4C+1N]环化反应合成多取代吡咯。
Chem Commun (Camb). 2011 Jan 14;47(2):809-11. doi: 10.1039/c0cc03802d. Epub 2010 Nov 11.
9
One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes through a catalytic tandem reaction using an amino acid lithium salt.一锅法利用氨基酸锂盐通过催化串联反应从醛和硝基烷烃不对称合成γ-硝基醛。
J Org Chem. 2011 Apr 1;76(7):2305-9. doi: 10.1021/jo102570p. Epub 2011 Mar 9.
10
Organocatalytic multicomponent synthesis of polysubstituted pyrroles from 1,2-diones, aldehydes and arylamines.通过1,2 - 二酮、醛和芳胺的有机催化多组分合成多取代吡咯。
Chem Commun (Camb). 2015 Dec 4;51(93):16652-5. doi: 10.1039/c5cc05624a. Epub 2015 Oct 1.

引用本文的文献

1
Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Brønsted Acid Approach to Tetrahydroindoles.环己酮、芳基胺和苯甲酰基亚甲基丙二酸酯的三组分串联反应:烯胺-布朗斯特酸协同法合成四氢吲哚。
ACS Omega. 2022 Nov 30;7(49):45341-45346. doi: 10.1021/acsomega.2c05909. eCollection 2022 Dec 13.
2
Navigating chemical reaction space - application to DNA-encoded chemistry.探索化学反应空间——在DNA编码化学中的应用
Chem Sci. 2022 Sep 1;13(37):11221-11231. doi: 10.1039/d2sc02474h. eCollection 2022 Sep 28.
3
Revisit to the synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives in lactic acid media as a green solvent and catalyst.
重新考察在乳酸介质中作为绿色溶剂和催化剂合成 1,2,3,4-四取代吡咯衍生物。
Mol Divers. 2021 Nov;25(4):2321-2338. doi: 10.1007/s11030-020-10122-1. Epub 2020 Sep 27.
4
Real-time monitoring of the reaction between aniline and acetonylacetone using extractive electorspray ionization tandem mass spectrometry.采用萃取电喷雾串联质谱法实时监测苯胺与乙酰丙酮的反应。
Sci Rep. 2019 Dec 17;9(1):19279. doi: 10.1038/s41598-019-55921-1.
5
DBU-mediated annulation of 2-aryl-3-nitro-2H-chromenes with 1,3-cyclohexanediones for the synthesis of benzofuro[2,3-c]chromenone derivatives.DBU 介导的 2-芳基-3-硝基-2H-色烯与 1,3-环己二酮的环化反应合成苯并呋喃[2,3-c]色酮衍生物。
Mol Divers. 2020 Feb;24(1):191-200. doi: 10.1007/s11030-019-09939-2. Epub 2019 Mar 23.
6
RhIII-Catalyzed Synthesis of Isoquinolones and 2-Pyridones via Annulation of -Methoxyamides and Nitroalkenes.铑(III)催化的通过甲氧基酰胺与硝基烯烃的环化反应合成异喹啉酮和2-吡啶酮。
European J Org Chem. 2018 Aug 31;2018(32):4381-4388. doi: 10.1002/ejoc.201800745. Epub 2018 Jun 11.
7
Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides.试剂控制的2-氨基苯并噻唑与β-酮酯和β-酮酰胺的区域发散性分子间环化反应
Beilstein J Org Chem. 2017 Dec 18;13:2739-2750. doi: 10.3762/bjoc.13.270. eCollection 2017.
8
Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.利用线性选择性氢酰化反应直接合成高度取代的吡咯和二氢吡咯。
Chemistry. 2016 Jun 1;22(23):7879-84. doi: 10.1002/chem.201600311. Epub 2016 Apr 23.
9
Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions.硅胶硫酸:一种可重复使用的固体催化剂,可在无溶剂条件下一锅法合成稠取代的吡咯并异香豆素。
Beilstein J Org Chem. 2013 Nov 4;9:2344-53. doi: 10.3762/bjoc.9.269. eCollection 2013.
10
A sustainable catalytic pyrrole synthesis.一种可持续的吡咯合成催化方法。
Nat Chem. 2013 Feb;5(2):140-4. doi: 10.1038/nchem.1547. Epub 2013 Jan 20.