• 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PIDA介导的分子内氧化C-N键形成反应从烯胺酮直接合成喹喔啉。

PIDA-mediated intramolecular oxidative C-N bond formation for the direct synthesis of quinoxalines from enaminones.

作者信息

Zhang Hong, Shen Jinhai, Yang Zhenhui, Cui Xiuling

机构信息

Engineering Research Center of Molecular Medicine of Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University Xiamen 361021 P. R. China

出版信息

RSC Adv. 2019 Mar 7;9(14):7718-7722. doi: 10.1039/c9ra01200a. eCollection 2019 Mar 6.

DOI:10.1039/c9ra01200a
PMID:35521175
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9061175/
Abstract

A intramolecular oxidative C(sp)-N bond formation mediated by hypervalent iodine(iii) to obtain quinoxalines from readily available -(2-acetaminophenyl)enaminones was developed. A tandem process involving PIDA-mediated intramolecular condensation cyclization and a subsequent elimination was postulated, which was highly efficient and metal-free under mild conditions. Moreover, flexible structural modifications of quinoxalines bearing carbonyl groups are of interest for further transformations as building blocks in organic synthesis.

摘要

开发了一种由高价碘（III）介导的分子内氧化C（sp）-N键形成反应，可从容易获得的α-（2-乙酰氨基苯基）烯胺酮制备喹喔啉。推测这是一个涉及PIDA介导的分子内缩合环化和随后消除反应的串联过程，该过程在温和条件下高效且无金属。此外，带有羰基的喹喔啉的灵活结构修饰作为有机合成中的构建块，对于进一步转化具有重要意义。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/d75d65b3aa60/c9ra01200a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/679b937dad21/c9ra01200a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/a6a9169e8012/c9ra01200a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/c2cba275b502/c9ra01200a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/e49111507c8f/c9ra01200a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/6b19b0fc34d6/c9ra01200a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/d75d65b3aa60/c9ra01200a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/679b937dad21/c9ra01200a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/a6a9169e8012/c9ra01200a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/c2cba275b502/c9ra01200a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/e49111507c8f/c9ra01200a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/6b19b0fc34d6/c9ra01200a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4a6/9061175/d75d65b3aa60/c9ra01200a-s5.jpg

相似文献

1
PIDA-mediated intramolecular oxidative C-N bond formation for the direct synthesis of quinoxalines from enaminones.通过PIDA介导的分子内氧化C-N键形成反应从烯胺酮直接合成喹喔啉。
RSC Adv. 2019 Mar 7;9(14):7718-7722. doi: 10.1039/c9ra01200a. eCollection 2019 Mar 6.
2
μ-Oxo-Hypervalent-Iodine-Catalyzed Oxidative C-H Amination for Synthesis of Benzolactam Derivatives.μ-氧代高碘酸催化氧化 C-H 胺化反应合成苯并内酰胺衍生物。
Chem Pharm Bull (Tokyo). 2022 Feb 1;70(2):106-110. doi: 10.1248/cpb.c21-00980. Epub 2021 Dec 11.
3
Hypervalent Iodine(III)-Mediated Counteranion Controlled Intramolecular Annulation of Exocyclic β-Enaminone to Carbazolone and Imidazo[1,2-a]pyridine Synthesis.高价碘（III）介导的环外β-烯胺酮的抗衡离子控制分子内环化反应合成咔唑酮和咪唑并[1,2-a]吡啶
Chemistry. 2019 Apr 23;25(23):5934-5939. doi: 10.1002/chem.201806299. Epub 2019 Apr 1.
4
Cyclic Hypervalent Iodine Reagents: Enabling Tools for Bond Disconnection via Reactivity Umpolung.环状高价碘试剂：通过反应性反转实现键断裂的有力工具。
Acc Chem Res. 2018 Dec 18;51(12):3212-3225. doi: 10.1021/acs.accounts.8b00468. Epub 2018 Nov 28.
5
Hypervalent iodine(III)-induced oxidative [4+2] annulation of o-phenylenediamines and electron-deficient alkynes: direct synthesis of quinoxalines from alkyne substrates under metal-free conditions.高价碘(III)诱导的邻苯二胺和缺电子炔烃的[4+2]环加成：无金属条件下从炔烃底物直接合成喹喔啉。
Chem Commun (Camb). 2013 Oct 18;49(81):9266-8. doi: 10.1039/c3cc45469j.
6
PIDA-Mediated Formal Olefinic C=C Bond Cleavage of α-Oxo-Ketene N,N-Acetals toward Substituted Oxazolines.PIDA 介导的 α-氧代-酮烯 N,N-缩醛的形式双键 C=C 键断裂生成取代恶唑啉。
Chemistry. 2018 Sep 25;24(54):14368-14372. doi: 10.1002/chem.201803466. Epub 2018 Aug 29.
7
Transition-metal-free approach to quinolines direct oxidative cyclocondensation reaction of ,-dimethyl enaminones with -aminobenzyl alcohols.无过渡金属合成喹啉的方法：α,β-二甲基烯胺酮与β-氨基苄醇的直接氧化环缩合反应
Front Chem. 2022 Sep 21;10:1008568. doi: 10.3389/fchem.2022.1008568. eCollection 2022.
8
Efficient synthesis of highly substituted Pyrrolin-4-ones via PIFA-mediated cyclization reactions of enaminones.通过PIFA介导的烯胺酮环化反应高效合成高度取代的吡咯啉-4-酮。
Org Lett. 2007 Dec 20;9(26):5345-8. doi: 10.1021/ol702362n. Epub 2007 Nov 30.
9
Hypervalent-Iodine(III)-Mediated Oxidative Methodology for the Synthesis of Fused Triazoles.高价碘（III）介导的氧化方法合成稠合三唑
Chem Asian J. 2016 Jul 20;11(14):1988-2000. doi: 10.1002/asia.201600119. Epub 2016 Jun 6.
10
I2 mediated synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones via sequential condensation/oxidative cyclization and rearrangement.碘介导的通过顺序缩合/氧化环化和重排合成5-取代-3-甲基/苄基-1,3,4-恶二唑-2(3H)-酮
Org Biomol Chem. 2016 Jun 15;14(24):5683-9. doi: 10.1039/c5ob02667a.

引用本文的文献

1
Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.高价碘（III）试剂在合成应用中的最新进展
Chem Rev. 2024 Oct 9;124(19):11108-11186. doi: 10.1021/acs.chemrev.4c00303. Epub 2024 Sep 13.
2
Iodine(III)-Mediated Oxidation of Anilines to Construct Dibenzazepines.碘(III)介导的苯胺氧化构建二苯并氮杂卓。
Chemistry. 2023 Jul 3;29(37):e202301141. doi: 10.1002/chem.202301141. Epub 2023 May 11.

本文引用的文献

1
The involvement of the trisulfur radical anion in electron-catalyzed sulfur insertion reactions: facile synthesis of benzothiazine derivatives under transition metal-free conditions.三硫自由基阴离子在电子催化硫插入反应中的作用：在无过渡金属条件下简便合成苯并噻嗪衍生物。
Chem Sci. 2016 Jul 1;7(7):4067-4072. doi: 10.1039/c6sc00240d. Epub 2016 Mar 11.
2
One-Pot Synthesis of Benzo[b][1,4]oxazins via Intramolecular Trapping Iminoenol.一锅法通过亚氨基烯醇的分子内捕获合成苯并[b][1,4]恶嗪
Org Lett. 2018 Feb 2;20(3):664-667. doi: 10.1021/acs.orglett.7b03804. Epub 2018 Jan 17.
3
Dendrimer-Stabilized Metal Nanoparticles as Efficient Catalysts for Reversible Dehydrogenation/Hydrogenation of N-Heterocycles.
树枝状聚合物稳定的金属纳米粒子作为高效催化剂用于 N-杂环化合物的可逆脱氢/加氢反应。
J Am Chem Soc. 2017 Dec 13;139(49):18084-18092. doi: 10.1021/jacs.7b10768. Epub 2017 Nov 30.
4
Benzodiazines: recent synthetic advances.苯二氮䓬类药物：最新的合成进展。
Chem Soc Rev. 2017 May 22;46(10):3060-3094. doi: 10.1039/c7cs00082k.
5
One-pot synthesis of thiazino[2,3,4-hi]indole derivatives through a tandem oxidative coupling/heteroannulation process.通过串联氧化偶联/杂环化过程一锅法合成噻嗪并[2,3,4-hi]吲哚衍生物。
Chem Commun (Camb). 2017 Apr 25;53(34):4718-4721. doi: 10.1039/c7cc00992e.
6
Novel 2-phenyl-4,5,6,7-tetrahydro[b]benzothiophene analogues as selective COX-2 inhibitors: Design, synthesis, anti-inflammatory evaluation, and molecular docking studies.新型2-苯基-4,5,6,7-四氢[b]苯并噻吩类似物作为选择性COX-2抑制剂：设计、合成、抗炎评价及分子对接研究
Bioorg Med Chem Lett. 2017 Apr 15;27(8):1721-1726. doi: 10.1016/j.bmcl.2017.02.076. Epub 2017 Mar 8.
7
Iodine/Copper Iodide-Mediated C-H Functionalization: Synthesis of Imidazo[1,2-a]pyridines and Indoles from N-Aryl Enamines.碘/碘化铜介导的 C-H 功能化：N-芳基烯胺合成咪唑并[1,2-a]吡啶和吲哚。
J Org Chem. 2016 Oct 7;81(19):9326-9336. doi: 10.1021/acs.joc.6b01960. Epub 2016 Sep 20.
8
The photoprotective effects of 2-benzoyl-3-phenylquinoxaline 1,4-dioxide against UVB-induced damage in HaCaT cells.2-苯甲酰基-3-苯基喹喔啉-1,4-二氧化物对HaCaT细胞中紫外线B诱导损伤的光保护作用。
Med Oncol. 2016 Aug;33(8):86. doi: 10.1007/s12032-016-0802-4. Epub 2016 Jul 4.
9
Copper-Catalyzed Cascade Cycloamination of α-Csp(3)-H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines.铜催化的氮杂环丙烷与叠氮化物的α-Csp(3)-H 键的级联环化反应：喹喔啉的合成。
Org Lett. 2016 May 6;18(9):2078-81. doi: 10.1021/acs.orglett.6b00709. Epub 2016 Apr 25.
10
Domino Reactions Based on Combinatorial Bond Transformations in Electron-Deficient Tertiary Enamines.基于贫电子叔烯胺中组合键转化的多米诺反应。
Chem Rec. 2016 Jun;16(3):1164-77. doi: 10.1002/tcr.201500296. Epub 2016 Apr 5.