• 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

一锅三组分铁催化合成苯并咪唑——多米诺C-N键形成反应

One-pot, three-component, iron-catalyzed synthesis of benzimidazoles domino C-N bond formation.

作者信息

Aboonajmi Jasem, Mohammadi Masoumeh, Panahi Farhad, Aberi Mahdi, Sharghi Hashem

机构信息

Department of Chemistry, College of Sciences, Shiraz University Shiraz 71454 Iran

Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg Albertstraße 21 79104 Freiburg im Breisgau Germany.

出版信息

RSC Adv. 2023 Aug 21;13(35):24789-24794. doi: 10.1039/d3ra04450e. eCollection 2023 Aug 11.

DOI:10.1039/d3ra04450e
PMID:37608969
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10440634/
Abstract

An efficient one-pot, three-component process for the synthesis of benzimidazole derivatives using a catalytic amount of Fe(iii) porphyrin has been developed. The reaction proceeds domino C-N bond formation and cyclization reactions of benzo-1,2-quinone, aldehydes and ammonium acetate as a nitrogen source to selectively produce benzimidazole. A number of benzimidazole derivatives have been synthesized using this method in high yields under mild reaction conditions.

摘要

已经开发出一种使用催化量的铁（III）卟啉合成苯并咪唑衍生物的高效一锅三组分方法。该反应通过苯并-1,2-醌、醛和作为氮源的醋酸铵进行多米诺C-N键形成和环化反应，以选择性地生成苯并咪唑。使用该方法在温和的反应条件下以高产率合成了多种苯并咪唑衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd40/10440634/76a32fedd0fc/d3ra04450e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd40/10440634/ab2922e297f0/d3ra04450e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd40/10440634/ca935a528954/d3ra04450e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd40/10440634/92d953e19ae4/d3ra04450e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd40/10440634/76a32fedd0fc/d3ra04450e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd40/10440634/ab2922e297f0/d3ra04450e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd40/10440634/ca935a528954/d3ra04450e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd40/10440634/92d953e19ae4/d3ra04450e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd40/10440634/76a32fedd0fc/d3ra04450e-s4.jpg

相似文献

1
One-pot, three-component, iron-catalyzed synthesis of benzimidazoles domino C-N bond formation.一锅三组分铁催化合成苯并咪唑——多米诺C-N键形成反应
RSC Adv. 2023 Aug 21;13(35):24789-24794. doi: 10.1039/d3ra04450e. eCollection 2023 Aug 11.
2
Copper-catalyzed domino addition/double cyclization: an approach to polycyclic benzimidazole derivatives.铜催化的多米诺加成/双环化反应：多环苯并咪唑衍生物的一种合成方法。
J Org Chem. 2014 Feb 21;79(4):1749-57. doi: 10.1021/jo402742k. Epub 2014 Feb 10.
3
Facile synthesis of substituted quinolines by iron(iii)-catalyzed cascade reaction between anilines, aldehydes and nitroalkanes.通过铁(III)催化的苯胺、醛和硝基烷烃之间的级联反应，简便合成取代喹啉。
Org Biomol Chem. 2019 Aug 28;17(34):7907-7917. doi: 10.1039/c9ob01294j.
4
Synthesis of Fused Dibenzofuran Derivatives via Palladium-Catalyzed Domino C-C Bond Formation and Iron-Catalyzed Cycloisomerization/Aromatization.通过钯催化的多米诺C-C键形成以及铁催化的环异构化/芳构化反应合成稠合二苯并呋喃衍生物
J Org Chem. 2016 Feb 5;81(3):1164-74. doi: 10.1021/acs.joc.5b02637. Epub 2016 Jan 14.
5
One-pot synthesis of α,β-epoxy ketones through domino reaction between alkenes and aldehydes catalyzed by proline based chiral organocatalysts.通过脯氨酸基手性有机催化剂催化的烯烃与醛之间的多米诺反应一锅法合成α,β-环氧酮。
Org Biomol Chem. 2017 Mar 22;15(12):2551-2561. doi: 10.1039/c7ob00031f.
6
Rhodium(III)-Catalyzed Directed C-H Amidation of N-Nitrosoanilines and Subsequent Formation of 1,2-Disubstituted Benzimidazoles.铑（III）催化的N-亚硝基苯胺的定向C-H酰胺化反应及随后1,2-二取代苯并咪唑的形成
Chem Asian J. 2017 Nov 2;12(21):2804-2808. doi: 10.1002/asia.201701287. Epub 2017 Oct 12.
7
Construction of indole- and isoquinoline-fused nitrogen-containing heterocycles through copper-catalyzed multi-component reaction.通过铜催化多组分反应构建吲哚和异喹啉稠合含氮杂环化合物
Yakugaku Zasshi. 2010 Jul;130(7):925-36. doi: 10.1248/yakushi.130.925.
8
Multistep divergent synthesis of benzimidazole linked benzoxazole/benzothiazole via copper catalyzed domino annulation.通过铜催化的多步发散合成法，将苯并咪唑连接的苯并恶唑/苯并噻唑进行环加成。
Org Biomol Chem. 2013 Apr 21;11(15):2473-81. doi: 10.1039/c3ob27177c. Epub 2013 Feb 22.
9
One-Pot Multicomponent Reaction of Catechols, Ammonium Acetate, and Aldehydes for the Synthesis of Benzoxazole Derivatives Using the Fe(III)-Salen Complex.使用 Fe(III)-Salen 配合物一锅法多组分反应合成苯并恶唑衍生物：儿茶酚、醋酸铵和醛。
J Org Chem. 2020 May 15;85(10):6567-6577. doi: 10.1021/acs.joc.0c00560. Epub 2020 May 6.
10
REGIOSELECTIVE MULTICOMPONENT DOMINO REACTIONS PROVIDING RAPID AND EFFICIENT ROUTES TO FUSED ACRIDINES.区域选择性多组分多米诺反应为稠合吖啶提供快速有效的合成途径。
Heterocycles. 2013 Dec 17;88(2):1065-1077. doi: 10.3987/COM-13-S(S)65.

引用本文的文献

1
Ni-containing l-glutamic acid cross-linked chitosan anchored on FeO/-MWCNT: a sustainable catalyst for the green reduction and one-pot two-step reductive Schotten-Baumann-type acetylation of nitroarenes.负载于FeO/-MWCNT上的含镍L-谷氨酸交联壳聚糖：用于硝基芳烃绿色还原及一锅两步还原型肖滕-鲍曼式乙酰化反应的可持续催化剂
Nanoscale Adv. 2024 Jun 25;6(15):3961-3977. doi: 10.1039/d4na00160e. eCollection 2024 Jul 23.

本文引用的文献

1
Iodine-catalyzed synthesis of benzoxazoles using catechols, ammonium acetate, and alkenes/alkynes/ketones C-C and C-O bond cleavage.碘催化利用邻苯二酚、醋酸铵和烯烃/炔烃/酮类进行苯并恶唑的合成及碳-碳和碳-氧键断裂。
RSC Adv. 2022 Jul 21;12(32):20968-20972. doi: 10.1039/d2ra03340b. eCollection 2022 Jul 14.
2
One-Pot Multicomponent Coupling Reaction of Catechols, Benzyl Alcohols/Benzyl Methyl Ethers, and Ammonium Acetate toward Synthesis of Benzoxazoles.邻苯二酚、苄醇/苄基甲基醚与醋酸铵的一锅多组分偶联反应用于合成苯并恶唑。
ACS Omega. 2021 Aug 18;6(34):22395-22399. doi: 10.1021/acsomega.1c03207. eCollection 2021 Aug 31.
3
The role of imidazole and benzimidazole heterocycles in Chagas disease: A review.
咪唑和苯并咪唑杂环在恰加斯病中的作用：综述
Eur J Med Chem. 2020 Nov 15;206:112692. doi: 10.1016/j.ejmech.2020.112692. Epub 2020 Aug 5.
4
Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron.手性二硼诱导亚胺的对映选择性还原偶联。
J Am Chem Soc. 2020 Jun 10;142(23):10337-10342. doi: 10.1021/jacs.0c04558. Epub 2020 May 29.
5
One-Pot Multicomponent Reaction of Catechols, Ammonium Acetate, and Aldehydes for the Synthesis of Benzoxazole Derivatives Using the Fe(III)-Salen Complex.使用 Fe(III)-Salen 配合物一锅法多组分反应合成苯并恶唑衍生物：儿茶酚、醋酸铵和醛。
J Org Chem. 2020 May 15;85(10):6567-6577. doi: 10.1021/acs.joc.0c00560. Epub 2020 May 6.
6
A new bis-phenolate mesoionic carbene ligand for early transition metal chemistry.一种用于早期过渡金属化学的新型双酚甲酚型偕二氮杂茂卡宾配体。
Dalton Trans. 2019 Oct 7;48(39):14611-14625. doi: 10.1039/c9dt03099a.
7
Metal-Organic Framework MIL-101(Cr) as an Efficient Heterogeneous Catalyst for Clean Synthesis of Benzoazoles.金属有机框架MIL-101（Cr）作为用于清洁合成苯并唑类的高效多相催化剂。
ACS Omega. 2018 Dec 12;3(12):17135-17144. doi: 10.1021/acsomega.8b02309. eCollection 2018 Dec 31.
8
Kinetic Resolution of Secondary Allyl Boronates and Their Application in the Synthesis of Homoallylic Amines.动力学拆分仲烯丙基硼酸酯及其在高烯丙基胺合成中的应用。
Chemistry. 2018 Nov 2;24(61):16262-16265. doi: 10.1002/chem.201804395. Epub 2018 Oct 9.
9
Oxidative Synthesis of Benzimidazoles, Quinoxalines, and Benzoxazoles from Primary Amines by ortho-Quinone Catalysis.邻醌催化的伯胺氧化合成苯并咪唑、喹喔啉和苯并恶唑。
Org Lett. 2017 Oct 20;19(20):5629-5632. doi: 10.1021/acs.orglett.7b02786. Epub 2017 Oct 2.
10
Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)-C(alkyl) Bond Cleavage.芳基烷基酮和 2-氨基苯胺的苯并咪唑通过碘催化氧化 C(CO)-C(烷基)键断裂生成。
J Org Chem. 2017 Apr 21;82(8):4422-4428. doi: 10.1021/acs.joc.7b00165. Epub 2017 Apr 10.