• 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

通过串联反应合成吲哚和喹啉衍生物的最新进展。

Recent advances in the synthesis of indole and quinoline derivatives through cascade reactions.

作者信息

Barluenga José, Rodríguez Félix, Fañanás Francisco J

机构信息

Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al CSIC, Universidad de Oviedo, Julián Clavería 8, E-33006 Oviedo, Spain.

出版信息

Chem Asian J. 2009 Jul 6;4(7):1036-48. doi: 10.1002/asia.200900018.

DOI:10.1002/asia.200900018
PMID:19360759
Abstract

Indoles and quinolines are ubiquitous structural motifs in many natural products and biologically active pharmaceuticals. The pursuit of synthetic efficiency has stimulated the design and development of new synthetic strategies to construct these heterocycles. One of the most effective ways of achieving efficiency is to implement reaction cascades, enabling multiple bond-forming and bond-cleaving events to occur in a single synthetic operation, thus circumventing the waste associated with traditional stepwise synthesis. In general, cascade reactions offer the opportunity to access highly functionalized final products from simple starting materials. For all these reasons, it is not a surprise that most of the recently reported methods for the synthesis of indoles and quinolines are based on the use of cascade reactions. In this Focus Review we discuss some of the most representative and interesting recent reports on the synthesis of indoles and quinolines through cascade reactions.

摘要

吲哚和喹啉是许多天然产物和生物活性药物中普遍存在的结构单元。对合成效率的追求推动了构建这些杂环的新合成策略的设计与开发。实现效率的最有效方法之一是实施反应串联,使多个成键和断键事件能在单一合成操作中发生,从而避免与传统逐步合成相关的浪费。一般来说,串联反应提供了从简单起始原料获得高度官能化最终产物的机会。基于所有这些原因,最近报道的大多数吲哚和喹啉合成方法基于串联反应的使用也就不足为奇了。在本重点综述中,我们讨论了一些关于通过串联反应合成吲哚和喹啉的最具代表性和趣味性的近期报道。

相似文献

1
Recent advances in the synthesis of indole and quinoline derivatives through cascade reactions.通过串联反应合成吲哚和喹啉衍生物的最新进展。
Chem Asian J. 2009 Jul 6;4(7):1036-48. doi: 10.1002/asia.200900018.
2
Pt(IV)-catalyzed hydroamination triggered cyclization: a strategy to fused pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, and indolo[3,2-c]quinolines.Pt(IV)催化的氢胺化引发环化:一种构建稠合吡咯并[1,2-a]喹喔啉、吲哚并[1,2-a]喹喔啉和吲哚并[3,2-c]喹啉的策略。
J Org Chem. 2010 May 21;75(10):3371-80. doi: 10.1021/jo100373w.
3
Synthesis of functionalized quinolines via Ugi and Pd-catalyzed intramolecular arylation reactions.通过乌吉反应和钯催化的分子内芳基化反应合成功能化喹啉。
J Comb Chem. 2006 Sep-Oct;8(5):696-704. doi: 10.1021/cc060066b.
4
Asymmetric catalytic cascade reactions for constructing diverse scaffolds and complex molecules.不对称催化级联反应构建多样骨架和复杂分子。
Acc Chem Res. 2015 Jul 21;48(7):1832-44. doi: 10.1021/acs.accounts.5b00217. Epub 2015 Jun 23.
5
Zinc-catalyzed reactions of ethenetricarboxylates with 2-(trimethylsilylethynyl)anilines leading to bridged quinoline derivatives.锌催化乙烯三羧酸盐与2-(三甲基甲硅烷基乙炔基)苯胺反应生成桥连喹啉衍生物。
Org Lett. 2009 Jul 2;11(13):2796-9. doi: 10.1021/ol900960q.
6
Development of cascade reactions for the concise construction of diverse heterocyclic architectures.级联反应在构建多样杂环骨架中的发展。
Acc Chem Res. 2012 Aug 21;45(8):1278-93. doi: 10.1021/ar200338s. Epub 2012 May 11.
7
Alternating iodonium-mediated reaction cascades giving indole- and quinoline-containing polycycles.交替的碘鎓介导反应级联生成含吲哚和喹啉的多环化合物。
Org Lett. 2008 May 15;10(10):1967-70. doi: 10.1021/ol800202u. Epub 2008 Apr 24.
8
Palladium-catalyzed approach for the general synthesis of (E)-2-arylmethylidene-N-tosylindolines and (E)-2-arylmethylidene-N-tosyl/nosyltetrahydroquinolines: access to 2-substituted indoles and quinolines.钯催化的通用合成(E)-2-芳基亚甲基-N-对甲苯磺酰基吲哚啉和(E)-2-芳基亚甲基-N-对甲苯磺酰基/硝酰基四氢喹啉的方法:2-取代吲哚和喹啉的合成途径。
J Org Chem. 2012 Jun 1;77(11):5108-19. doi: 10.1021/jo300458v. Epub 2012 May 22.
9
Synthesis of indolylquinolines, indolylacridines, and indolylcyclopenta[b]quinolines from the Baylis-Hillman adducts: an in situ [1,3]-sigmatropic rearrangement of an indole nucleus to access indolylacridines and indolylcyclopenta[b]quinolines.从 Baylis-Hillman 加成物合成吲哚喹啉、吲哚吖啶和吲哚并环戊[b]喹啉:吲哚核的原位[1,3]-σ重排以获得吲哚吖啶和吲哚并环戊[b]喹啉。
J Org Chem. 2012 Oct 5;77(19):8451-64. doi: 10.1021/jo301313m. Epub 2012 Sep 25.
10
Recent advances in aryl-aryl bond formation by direct arylation.通过直接芳基化形成芳基-芳基键的最新进展。
Chem Soc Rev. 2009 Aug;38(8):2447-64. doi: 10.1039/b805701j. Epub 2009 May 22.

引用本文的文献

1
Vistas in the domain of 3-acetyl-4-hydroxy-2-quinolinone derivatives (AHQ) and their applications.3-乙酰基-4-羟基-2-喹啉酮衍生物(AHQ)领域的前景及其应用。
RSC Adv. 2025 Jun 4;15(23):18034-18088. doi: 10.1039/d5ra02813b. eCollection 2025 May 29.
2
2-Azidobenzaldehyde-Based [4+2] Annulation for the Synthesis of Quinoline Derivatives.基于2-叠氮苯甲醛的[4+2]环化反应合成喹啉衍生物
Molecules. 2024 Mar 11;29(6):1241. doi: 10.3390/molecules29061241.
3
Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of -Ethoxycarbonyl--Propargylanilines.
通过金催化的 -乙氧羰基--丙炔苯胺的分子内氢芳基化反应合成 4-取代-1,2-二氢喹啉。
Molecules. 2021 Jun 2;26(11):3366. doi: 10.3390/molecules26113366.
4
Synthetic and medicinal perspective of quinolines as antiviral agents.喹啉作为抗病毒药物的合成及药用前景。
Eur J Med Chem. 2021 Apr 5;215:113220. doi: 10.1016/j.ejmech.2021.113220. Epub 2021 Jan 24.
5
Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.炔酸酯作为在过渡金属催化下快速构建多样杂环的多功能、强效化学工具:最新进展与挑战。
Top Curr Chem (Cham). 2021 Jan 5;379(1):3. doi: 10.1007/s41061-020-00316-4.
6
Gold-Catalyzed Hydroalkoxylation/Povarov Reaction Cascade of Alkynols with -Aryl Imines: Synthesis of Tetrahydroquinolines.金催化炔醇与芳基亚胺的氢烷氧基化/波瓦罗夫反应串联:四氢喹啉的合成
ACS Omega. 2019 Sep 9;4(13):15754-15763. doi: 10.1021/acsomega.9b02693. eCollection 2019 Sep 24.
7
Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis.电化学和光氧化还原催化:在有机合成中的比较评价。
Molecules. 2019 Jun 5;24(11):2122. doi: 10.3390/molecules24112122.
8
Palladium-Catalysed Synthesis and Transformation of Quinolones.钯催化喹诺酮类化合物的合成与转化。
Molecules. 2019 Jan 9;24(2):228. doi: 10.3390/molecules24020228.
9
Fe(III)-Catalyzed Bicyclization of Yne-Allenones With Indoles for the Atom-Economic Synthesis of 3-Indolyl Cyclobutarenes.铁(III)催化的烯炔烯酮与吲哚的双环化反应用于3-吲哚基环丁芳烃的原子经济性合成。
Front Chem. 2018 Dec 4;6:599. doi: 10.3389/fchem.2018.00599. eCollection 2018.
10
Design and synthesis of an indol derivative as antibacterial agent against .作为抗……的抗菌剂的吲哚衍生物的设计与合成。 (原文中“against”后缺少具体对象)
J Chem Biol. 2017 Jun 8;10(4):159-177. doi: 10.1007/s12154-017-0173-0. eCollection 2017 Oct.