• 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

KSO在无金属、无光催化剂和无光照条件下介导喹喔啉-2(1)-酮的C-3芳基化反应。

KSO mediated C-3 arylation of quinoxalin-2(1)-ones under metal-, photocatalyst- and light-free conditions.

作者信息

Dutta Nibedita Baruah, Bhuyan Mayurakhi, Baishya Gakul

机构信息

Chemical Science & Technology Division, CSIR-North East Institute of Science and Technology Jorhat-785006 India

Academy of Scientific and Innovative Research Ghaziabad Uttar Pradesh-201002 India.

出版信息

RSC Adv. 2020 Jan 22;10(6):3615-3624. doi: 10.1039/d0ra00013b. eCollection 2020 Jan 16.

DOI:10.1039/d0ra00013b
PMID:35497762
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9048439/
Abstract

Two facile and effective C-3 arylation protocols of quinoxalin-2(1)-ones with arylhydrazines and aryl boronic acids respectively free radical cross-coupling reactions under metal-, photocatalyst- and light-free conditions have been unveiled. KSO has been used as an efficient oxidant to generate aryl radicals from arylhydrazines and aryl boronic acids under two different reaction conditions. The generated aryl radicals undergo a free radical coupling reaction at the C-3 position of quinoxalin-2(1)-ones producing 3-arylquinoxalin-2(1)-ones in good to excellent yields. The involvement of radicals in the course of the reaction has been demonstrated by radical trapping experiments with 2,2,6,6-tetramethylpiperidine-1-oxyl.

摘要

分别报道了两种简便有效的喹喔啉-2(1)-酮与芳基肼和芳基硼酸的C-3芳基化反应方法，即在无金属、无光催化剂和无光照条件下的自由基交叉偶联反应。在两种不同的反应条件下，KSO被用作一种有效的氧化剂，从芳基肼和芳基硼酸中生成芳基自由基。所生成的芳基自由基在喹喔啉-2(1)-酮的C-3位发生自由基偶联反应，以良好到优异的产率生成3-芳基喹喔啉-2(1)-酮。通过2,2,6,6-四甲基哌啶-1-氧基的自由基捕获实验证明了反应过程中自由基的参与。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/6f693cb1f255/d0ra00013b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/ea2c6abdee9e/d0ra00013b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/203001e7ca81/d0ra00013b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/4787a52da273/d0ra00013b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/6e451a561ce9/d0ra00013b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/6f693cb1f255/d0ra00013b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/ea2c6abdee9e/d0ra00013b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/203001e7ca81/d0ra00013b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/4787a52da273/d0ra00013b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/6e451a561ce9/d0ra00013b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f2b/9048439/6f693cb1f255/d0ra00013b-s5.jpg

相似文献

1
KSO mediated C-3 arylation of quinoxalin-2(1)-ones under metal-, photocatalyst- and light-free conditions.KSO在无金属、无光催化剂和无光照条件下介导喹喔啉-2(1)-酮的C-3芳基化反应。
RSC Adv. 2020 Jan 22;10(6):3615-3624. doi: 10.1039/d0ra00013b. eCollection 2020 Jan 16.
2
Metal-free three-component cyanoalkylation of quinoxalin-2(1)-ones with vinylarenes and azobis(alkylcarbonitrile)s.无金属参与的喹喔啉-2(1H)-酮、取代乙烯基芳烃和偶氮二异丁腈的三组分氰烷基化反应。
Org Biomol Chem. 2022 Feb 16;20(7):1462-1474. doi: 10.1039/d1ob02143e.
3
Metal-Free Direct C3-H Alkylation and Arylation of Quinoxalin-2(1H)-Ones with Inert Alkyl and Aryl Chlorides.喹喔啉-2(1H)-酮与惰性烷基和芳基氯化物的无金属直接C3-H烷基化和芳基化反应
Chemistry. 2023 Aug 21;29(47):e202300774. doi: 10.1002/chem.202300774. Epub 2023 Jul 24.
4
-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1)-ones with 4-hydroxycoumarins, 4-hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions.-无金属条件下丁基过氧化氢（TBHP）介导的喹喔啉-2（1H）-酮与 4-羟基香豆素、4-羟基-6-甲基-2-吡喃酮和 2-羟基-1,4-萘醌的氧化交叉脱氢偶联。
Org Biomol Chem. 2020 Aug 26;18(33):6537-6548. doi: 10.1039/d0ob01304h.
5
Base-Mediated Visible-Light-Driven C-H Arylation of Quinoxalin-2(1)-Ones in Ethanol.乙醇中碱介导的喹喔啉-2(1)-酮的可见光驱动C-H芳基化反应
J Org Chem. 2024 Oct 4;89(19):14217-14227. doi: 10.1021/acs.joc.4c01641. Epub 2024 Sep 26.
6
Photocatalyst-Free Visible Light-Induced C(sp)-H Arylation of Quinoxalin-2(1H)-ones and Coumarins.无光催化剂可见光诱导喹喔啉-2(1H)-酮和香豆素的C(sp)-H芳基化反应
Chemistry. 2024 Aug 6;30(44):e202401371. doi: 10.1002/chem.202401371. Epub 2024 Jul 17.
7
Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts.可见光诱导喹喔啉-2(1)-酮的自由基级联官能团化反应：与苯乙烯和噻蒽鎓盐的三组分1,2-二（杂）芳基化方法
Org Lett. 2024 Oct 18;26(41):8821-8826. doi: 10.1021/acs.orglett.4c03565. Epub 2024 Oct 9.
8
Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1)-ones.喹喔啉-2(1)-酮的成对电解促进芳基化反应
J Org Chem. 2024 May 3;89(9):6117-6125. doi: 10.1021/acs.joc.4c00087. Epub 2024 Apr 24.
9
A visible-light-mediated cascade reaction of quinoxalin-2(1)-ones, alkenes, and sulfinic acids.可见光促进的喹喔啉-2(1H)-酮、烯烃和亚磺酸的级联反应。
Org Biomol Chem. 2023 May 17;21(19):4109-4113. doi: 10.1039/d3ob00448a.
10
Selectfluor-Mediated Regioselective C-3 Alkoxylation, Amination, Sulfenylation, and Selenylation of Quinoxalin-2(1)-ones.氟代 Selectfluor 促进的喹喔啉-2(1H)-酮的 C-3 区域选择性烷氧基化、氨基化、硫代化和硒代化反应。
J Org Chem. 2023 Feb 17;88(4):2344-2357. doi: 10.1021/acs.joc.2c02756. Epub 2023 Feb 3.

引用本文的文献

1
Visible-Light-Induced Singlet Oxygen-Promoted Arylation and Alkylation of Quinoxalin-2(1H)-ones and Quinolines.可见光诱导的单线态氧促进喹喔啉-2(1H)-酮和喹啉的芳基化和烷基化反应
Molecules. 2024 Oct 29;29(21):5113. doi: 10.3390/molecules29215113.
2
Anticancer-active 3,4-diarylthiolated maleimides synthesis three-component radical diarylthiolation.具有抗癌活性的3,4-二芳基硫醇化马来酰亚胺的合成——三组分自由基二芳基硫醇化反应
Front Chem. 2022 Nov 25;10:1089860. doi: 10.3389/fchem.2022.1089860. eCollection 2022.
3
Sunlight Induced and Recyclable g-CN Catalyzed C-H Sulfenylation of Quinoxalin-2(1)-Ones.

本文引用的文献

1
Arylhydrazines: novel and versatile electrophilic partners in cross-coupling reactions.芳基肼：交叉偶联反应中新型且通用的亲电试剂
RSC Adv. 2018 Oct 1;8(59):33828-33844. doi: 10.1039/c8ra06423g. eCollection 2018 Sep 28.
2
Metal-, Photocatalyst-, and Light-Free, Late-Stage C-H Alkylation of Heteroarenes and 1,4-Quinones Using Carboxylic Acids.金属、光催化剂和光自由的，利用羧酸进行杂芳环和 1,4-醌的后期 C-H 烷基化反应。
Org Lett. 2018 Nov 2;20(21):6863-6867. doi: 10.1021/acs.orglett.8b02988. Epub 2018 Oct 24.
3
Transition-Metal-Free Direct C-H Arylation of Quinoxalin-2(1H)-ones with Diaryliodonium Salts at Room Temperature.
阳光诱导和可回收 g-CN 催化的喹喔啉-2(1H)-酮的 C-H 硫代化反应。
Molecules. 2022 Aug 8;27(15):5044. doi: 10.3390/molecules27155044.
室温条件下二芳基碘盐促进的喹喔啉-2(1H)-酮的无过渡金属直接 C-H 芳基化反应。
Org Lett. 2017 Apr 7;19(7):1530-1533. doi: 10.1021/acs.orglett.7b00310. Epub 2017 Mar 16.
4
Diastereoselective synthesis of tetrahydropyrans via Prins-Ritter and Prins-arylthiolation cyclization reactions.通过普林斯-里特反应和普林斯-芳基硫醇化环化反应实现四氢吡喃的非对映选择性合成。
Org Biomol Chem. 2017 Mar 1;15(9):2003-2012. doi: 10.1039/c6ob02692c.
5
CFTR activator increases intestinal fluid secretion and normalizes stool output in a mouse model of constipation.CFTR激活剂可增加便秘小鼠模型的肠道液体分泌并使粪便排出量正常化。
Cell Mol Gastroenterol Hepatol. 2016 May;2(3):317-327. doi: 10.1016/j.jcmgh.2015.12.010. Epub 2016 Jan 9.
6
Quinoxaline-Based Scaffolds Targeting Tyrosine Kinases and Their Potential Anticancer Activity.靶向酪氨酸激酶的喹喔啉类骨架及其潜在抗癌活性
Arch Pharm (Weinheim). 2016 May;349(5):309-26. doi: 10.1002/ardp.201500468. Epub 2016 Apr 9.
7
Design, synthesis and anti-HIV-1 evaluation of hydrazide-based peptidomimetics as selective gelatinase inhibitors.基于酰肼的拟肽作为选择性明胶酶抑制剂的设计、合成及抗HIV-1活性评价
Bioorg Med Chem. 2016 May 1;24(9):2125-36. doi: 10.1016/j.bmc.2016.03.043. Epub 2016 Mar 26.
8
Quinoxalinone (Part II). Discovery of (Z)-3-(2-(pyridin-4-yl)vinyl)quinoxalinone derivates as potent VEGFR-2 kinase inhibitors.喹喔啉酮（第二部分）。(Z)-3-(2-(吡啶-4-基)乙烯基)喹喔啉酮衍生物作为有效的血管内皮生长因子受体-2激酶抑制剂的发现。
Bioorg Med Chem. 2016 Apr 15;24(8):1840-52. doi: 10.1016/j.bmc.2016.03.008. Epub 2016 Mar 3.
9
Pd(OAc)2 in WERSA: a novel green catalytic system for Suzuki-Miyaura cross-coupling reactions at room temperature.在WERSA中的醋酸钯：一种用于室温下铃木-宫浦交叉偶联反应的新型绿色催化体系。
Chem Commun (Camb). 2015 Jul 21;51(57):11489-92. doi: 10.1039/c5cc04561d.
10
Iodine-Mediated C-H Functionalization of sp, sp(2), and sp(3) Carbon: A Unified Multisubstrate Domino Approach for Isatin Synthesis.碘介导的sp、sp(2)和sp(3)碳的C-H官能化：一种用于异吲哚酮合成的统一多底物多米诺方法。
J Org Chem. 2015 May 15;80(10):5167-75. doi: 10.1021/acs.joc.5b00581. Epub 2015 May 4.