• 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

通往芳基吡啶并吲唑鎓盐的新型氧化途径。

Novel oxidative routes to -arylpyridoindazolium salts.

作者信息

Levitskiy Oleg A, Grishin Yuri K, Magdesieva Tatiana V

机构信息

Chemistry Department, Lomonosov Moscow State University, Leninskie Gory, 1/3, Moscow, 119234, Russia.

出版信息

Beilstein J Org Chem. 2024 Aug 7;20:1906-1913. doi: 10.3762/bjoc.20.166. eCollection 2024.

DOI:10.3762/bjoc.20.166
PMID:39135660
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11318609/
Abstract

A novel facile approach to -arylpyridoindazolium salts is proposed, based on direct oxidation of the -pyridine substituted diarylamines, either using bis(trifluoroacetoxy)iodobenzene as an oxidant, or electrochemically, via potentiostatic oxidation. Electrochemical synthesis occurs under mild conditions; no chemical reagents are required except electric current. Both approaches can be considered as a late-stage functionalization; easily available -pyridyl-substituted diarylamines are used as the precursors.

摘要

基于对吡啶取代二芳基胺的直接氧化,提出了一种制备芳基吡啶并吲唑鎓盐的新颖简便方法,可使用双(三氟乙酰氧基)碘苯作为氧化剂进行氧化,也可通过恒电位氧化进行电化学氧化。电化学合成在温和条件下进行;除电流外无需化学试剂。这两种方法都可视为后期功能化;易于获得的吡啶基取代二芳基胺用作前体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/4e62ee080fa2/Beilstein_J_Org_Chem-20-1906-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/92b478f914e1/Beilstein_J_Org_Chem-20-1906-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/d2e40fd88ede/Beilstein_J_Org_Chem-20-1906-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/14808762b76b/Beilstein_J_Org_Chem-20-1906-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/9f263d263915/Beilstein_J_Org_Chem-20-1906-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/14e75c8fa183/Beilstein_J_Org_Chem-20-1906-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/6a76adf2a48a/Beilstein_J_Org_Chem-20-1906-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/767e8485b4df/Beilstein_J_Org_Chem-20-1906-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/4e62ee080fa2/Beilstein_J_Org_Chem-20-1906-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/92b478f914e1/Beilstein_J_Org_Chem-20-1906-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/d2e40fd88ede/Beilstein_J_Org_Chem-20-1906-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/14808762b76b/Beilstein_J_Org_Chem-20-1906-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/9f263d263915/Beilstein_J_Org_Chem-20-1906-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/14e75c8fa183/Beilstein_J_Org_Chem-20-1906-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/6a76adf2a48a/Beilstein_J_Org_Chem-20-1906-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/767e8485b4df/Beilstein_J_Org_Chem-20-1906-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5b1/11318609/4e62ee080fa2/Beilstein_J_Org_Chem-20-1906-g005.jpg

相似文献

1
Novel oxidative routes to -arylpyridoindazolium salts.通往芳基吡啶并吲唑鎓盐的新型氧化途径。
Beilstein J Org Chem. 2024 Aug 7;20:1906-1913. doi: 10.3762/bjoc.20.166. eCollection 2024.
2
-Functionalized Pyridinium Salts: A New Chapter for Site-Selective Pyridine C-H Functionalization via Radical-Based Processes under Visible Light Irradiation.-功能化吡啶盐:通过可见光照射下基于自由基的过程实现吡啶C-H位点选择性功能化的新篇章。
Acc Chem Res. 2022 Oct 18;55(20):3043-3056. doi: 10.1021/acs.accounts.2c00530. Epub 2022 Sep 27.
3
Electrochemical Oxidative Cross-Coupling with Hydrogen Evolution Reactions.电化学氧化交叉偶联与析氢反应。
Acc Chem Res. 2019 Dec 17;52(12):3309-3324. doi: 10.1021/acs.accounts.9b00512. Epub 2019 Nov 27.
4
Metal-free late-stage C(sp)-H functionalization of N-aryl amines with various sodium salts.无金属的 N-芳基胺的 C(sp2)-H 后期功能化与各种钠盐。
Org Biomol Chem. 2020 Jan 22;18(3):450-464. doi: 10.1039/c9ob02217a.
5
Site-Selective C-H Functionalization via Synergistic Use of Electrochemistry and Transition Metal Catalysis.通过电化学与过渡金属催化协同作用实现的位点选择性C-H官能团化
Acc Chem Res. 2020 Feb 18;53(2):300-310. doi: 10.1021/acs.accounts.9b00603. Epub 2020 Jan 15.
6
5,11-Diazadibenzo[hi,qr]tetracene: Synthesis, Properties, and Reactivity toward Nucleophilic Reagents.5,11-二氮杂二苯并[hi,qr]并四苯:合成、性质及对亲核试剂的反应活性
Chemistry. 2021 Jun 21;27(35):8951-8955. doi: 10.1002/chem.202100944. Epub 2021 May 17.
7
Synthesis of Complex Diarylamines through a Ring-Opening Difunctionalization Strategy.通过开环双官能团化策略合成复杂二芳基胺
Angew Chem Int Ed Engl. 2023 Nov 27;62(48):e202310921. doi: 10.1002/anie.202310921. Epub 2023 Oct 27.
8
Heavily Substituted Atropisomeric Diarylamines by Unactivated Smiles Rearrangement of N-Aryl Anthranilamides.通过 N-芳基邻氨基苯甲酰胺的非活化 Smiles 重排反应得到的重取代的非对映异构二芳基胺。
Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12533-12537. doi: 10.1002/anie.201706341. Epub 2017 Sep 6.
9
Cyclization of Azobenzenes Via Electrochemical Oxidation Induced Benzylic Radical Generation.通过电化学氧化诱导苄基自由基生成实现偶氮苯的环化反应。
Org Lett. 2023 Aug 18;25(32):5978-5983. doi: 10.1021/acs.orglett.3c02099. Epub 2023 Aug 7.
10
Synthesis of Cyclic and Acyclic ortho-Aryloxy Diaryliodonium Salts for Chemoselective Functionalizations.环状和非环状邻芳氧基二芳基碘鎓盐的合成及其用于选择性官能化反应。
Chemistry. 2022 Dec 9;28(69):e202202453. doi: 10.1002/chem.202202453. Epub 2022 Oct 19.

引用本文的文献

1
A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)-Schiff base complexes.一种用于镍(II)-席夫碱配合物中氨基酸手性官能化的新型氧化稳定配体。
Beilstein J Org Chem. 2023 Apr 27;19:566-574. doi: 10.3762/bjoc.19.41. eCollection 2023.

本文引用的文献

1
Electrochemical Synthesis of Aryl Dibenzothiophenium Triflates as Precursors for Selective Nucleophilic Aromatic (Radio)fluorination.电化学合成芳基二苯并噻吩三氟甲磺酸盐作为选择性亲核芳香(放射性)氟化反应的前体。
Org Lett. 2024 Apr 12;26(14):2790-2794. doi: 10.1021/acs.orglett.3c02921. Epub 2023 Oct 8.
2
Hybrid Azine Derivatives: A Useful Approach for Antimicrobial Therapy.杂化吖嗪衍生物:抗菌治疗的一种有效方法。
Pharmaceutics. 2022 Sep 23;14(10):2026. doi: 10.3390/pharmaceutics14102026.
3
Pyridine-Containing Donor-Acceptor Diarylnitroxides: Noncovalent Stabilization of the Redox States.
含吡啶的供体-受体二芳基氮氧化物:氧化还原态的非共价稳定作用
Chempluschem. 2022 Mar;87(3):e202100508. doi: 10.1002/cplu.202100508. Epub 2021 Dec 29.
4
Organic Electrosynthesis Towards Sustainability: Fundamentals and Greener Methodologies.迈向可持续发展的有机电合成:基础与更绿色的方法
Chem Rec. 2021 Sep;21(9):2453-2471. doi: 10.1002/tcr.202100128. Epub 2021 May 5.
5
A Comprehensive Review on Fused Heterocyclic as DNA Intercalators: Promising Anticancer Agents.融合杂环作为 DNA 嵌入剂的综合评述:有前途的抗癌剂。
Curr Pharm Des. 2021;27(1):15-42. doi: 10.2174/1381612826666201118113311.
6
Modern advances in heterocyclic chemistry in drug discovery.药物研发中杂环化学的现代进展。
Org Biomol Chem. 2016 Jul 12;14(28):6611-37. doi: 10.1039/c6ob00936k.
7
Recent advances in small organic molecules as DNA intercalating agents: synthesis, activity, and modeling.作为DNA嵌入剂的小分子有机化合物的最新进展:合成、活性及模型构建
Eur J Med Chem. 2014 Mar 3;74:95-115. doi: 10.1016/j.ejmech.2013.11.029. Epub 2014 Jan 3.
8
Synthesis of two new heteroaromatic beta-carboline-fused pentacycles. Observation of a new intercalating agent.两种新型杂芳基β-咔啉稠合五环的合成。一种新型嵌入剂的观察。
Bioorg Med Chem Lett. 2000 Aug 7;10(15):1767-9. doi: 10.1016/s0960-894x(00)00339-5.