• 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

通过铃木-宫浦交叉偶联反应合成新型三环芳基喹唑啉衍生物

New Tricyclic Aryl Quinazoline Derivatives by Suzuki-Miyaura Cross-Coupling.

作者信息

Elmuradov Burkhon, Okmanov Rasul, Juraev Bakhromjon, Dräger Gerald, Butenschön Holger

机构信息

Leibniz Universität Hannover, Institut für Organische Chemie, Schneiderberg 1B, D-30167, Hannover, Germany.

Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, 100170, Mirzo-Ulugbek str. 77, Tashkent, Uzbekistan.

出版信息

ChemistryOpen. 2024 Dec;13(12):e202400197. doi: 10.1002/open.202400197. Epub 2024 Sep 27.

DOI:10.1002/open.202400197
PMID:39329258
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11625927/
Abstract

A number of new deoxyvasicinone (2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one) and mackinazolinone (6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one) derivatives with aryl substituents at C7/C8 and at C5 are reported. These compounds are rare representatives of their kind and were prepared in high yields by Suzuki-Miyaura cross-coupling reactions between 7-bromo-2,3-dihydro[2,1-b]quinazoline-9-(1H)-one, 5,7-dibromo-2,3-dihydro[2,1-b]quinazoline-9-(1H)-one or 8-bromomackinazolinone and respective arylboronic acids with palladium acetate as the catalyst. The products were characterized spectroscopically and, in addition, by X-ray crystal structure analyses in six cases.

摘要

报道了一些在C7/C8和C5处带有芳基取代基的新型去氧哇巴因酮（2,3-二氢吡咯并[2,1-b]喹唑啉-9(1H)-酮）和麦基那唑啉酮（6,7,8,9-四氢-11H-吡啶并[2,1-b]喹唑啉-11-酮）衍生物。这些化合物是该类化合物中罕见的代表物，通过7-溴-2,3-二氢[2,1-b]喹唑啉-9-(1H)-酮、5,7-二溴-2,3-二氢[2,1-b]喹唑啉-9-(1H)-酮或8-溴麦基那唑啉酮与相应的芳基硼酸在醋酸钯作为催化剂的条件下进行铃木-宫浦交叉偶联反应，以高收率制备得到。对产物进行了光谱表征，此外，还对其中6个案例进行了X射线晶体结构分析。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/9edb2306ee60/OPEN-13-e202400197-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/d798c5c2b0c5/OPEN-13-e202400197-g030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/14a554fef9c2/OPEN-13-e202400197-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/b6397102f130/OPEN-13-e202400197-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/05fb9bc69700/OPEN-13-e202400197-g029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/5d9eba9763df/OPEN-13-e202400197-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/df339df5e5de/OPEN-13-e202400197-g031.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/96ed1e846e5b/OPEN-13-e202400197-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/a17195bd23ad/OPEN-13-e202400197-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/af1370d8129a/OPEN-13-e202400197-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/4a24ed1ba600/OPEN-13-e202400197-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/0281a0c61982/OPEN-13-e202400197-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/e53270cdc6d2/OPEN-13-e202400197-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/e73886eb920a/OPEN-13-e202400197-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/9edb2306ee60/OPEN-13-e202400197-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/d798c5c2b0c5/OPEN-13-e202400197-g030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/14a554fef9c2/OPEN-13-e202400197-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/b6397102f130/OPEN-13-e202400197-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/05fb9bc69700/OPEN-13-e202400197-g029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/5d9eba9763df/OPEN-13-e202400197-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/df339df5e5de/OPEN-13-e202400197-g031.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/96ed1e846e5b/OPEN-13-e202400197-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/a17195bd23ad/OPEN-13-e202400197-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/af1370d8129a/OPEN-13-e202400197-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/4a24ed1ba600/OPEN-13-e202400197-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/0281a0c61982/OPEN-13-e202400197-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/e53270cdc6d2/OPEN-13-e202400197-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/e73886eb920a/OPEN-13-e202400197-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ce3b/11625927/9edb2306ee60/OPEN-13-e202400197-g005.jpg

相似文献

1
New Tricyclic Aryl Quinazoline Derivatives by Suzuki-Miyaura Cross-Coupling.通过铃木-宫浦交叉偶联反应合成新型三环芳基喹唑啉衍生物
ChemistryOpen. 2024 Dec;13(12):e202400197. doi: 10.1002/open.202400197. Epub 2024 Sep 27.
2
Suzuki-Miyaura cross-coupling reactions of halo derivatives of 4H-pyrido[1,2-a]pyrimidin-4-ones.4H-吡啶并[1,2-a]嘧啶-4-酮的卤代衍生物的铃木-宫浦交叉偶联反应。
Org Biomol Chem. 2011 Oct 7;9(19):6559-65. doi: 10.1039/c1ob05505d. Epub 2011 Aug 2.
3
Palladium-catalysed cross-coupling reaction of ultra-stabilised 2-aryl-1,3-dihydro-1H-benzo[d]1,3,2-diazaborole compounds with aryl bromides: A direct protocol for the preparation of unsymmetrical biaryls.钯催化的超稳定 2-芳基-1,3-二氢-1H-苯并[d]1,3,2-二氮杂硼杂环戊烷化合物与芳基溴化物的交叉偶联反应：一种直接制备不对称联芳烃的方法。
Beilstein J Org Chem. 2014 May 13;10:1107-13. doi: 10.3762/bjoc.10.109. eCollection 2014.
4
Heterogeneous Pd/C-catalyzed, ligand free Suzuki-Miyaura coupling reaction furnishes new -terphenyl derivatives.无配体的多相 Pd/C 催化Suzuki-Miyaura 偶联反应提供了新的三联苯衍生物。
Nat Prod Res. 2022 Jan;36(2):566-570. doi: 10.1080/14786419.2020.1791112. Epub 2020 Jul 13.
5
N-heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of aryl sulfonates with arylboronic acids.N-杂环卡宾-钯（II）-1-甲基咪唑配合物催化的芳基磺酸盐与芳基硼酸的Suzuki-Miyaura 偶联反应。
J Org Chem. 2012 Aug 3;77(15):6608-14. doi: 10.1021/jo301270t. Epub 2012 Jul 25.
6
Pyrrolodiazines. 6. Palladium-catalyzed arylation, heteroarylation, and amination of 3,4-dihydropyrrolo[1,2-a]pyrazines.吡咯并二嗪。6. 钯催化的3,4-二氢吡咯并[1,2-a]吡嗪的芳基化、杂芳基化和胺化反应
J Org Chem. 2004 Dec 10;69(25):8668-75. doi: 10.1021/jo048898o.
7
Suzuki-Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium complex catalyst.聚合物负载的 N-杂环卡宾-钯配合物催化剂催化 1-芳基三氮唑与芳基硼酸的铃木-宫浦交叉偶联反应。
Beilstein J Org Chem. 2010 Jun 28;6:70. doi: 10.3762/bjoc.6.70.
8
Preparation of Synthetic and Natural Derivatives of Flavonoids Using Suzuki-Miyaura Cross-Coupling Reaction.使用 Suzuki-Miyaura 交叉偶联反应制备黄酮类化合物的合成和天然衍生物。
Molecules. 2022 Jan 31;27(3):967. doi: 10.3390/molecules27030967.
9
Recoverable Palladium-Catalyzed Carbon-Carbon Bond Forming Reactions under Thermomorphic Mode: Stille and Suzuki-Miyaura Reactions.可恢复的热致变色模式下的钯催化碳-碳键形成反应：Stille 和 Suzuki-Miyaura 反应。
Molecules. 2021 Mar 5;26(5):1414. doi: 10.3390/molecules26051414.
10
Facile synthesis of 6-aryl 5-N-substituted pyridazinones: microwave-assisted Suzuki-Miyaura cross coupling of 6-chloropyridazinones.6-芳基-5-N-取代哒嗪酮的简便合成：6-氯哒嗪酮的微波辅助铃木-宫浦交叉偶联反应
J Org Chem. 2008 Sep 19;73(18):7204-8. doi: 10.1021/jo801097v. Epub 2008 Aug 8.

本文引用的文献

1
Novel deoxyvasicinone derivatives as potent multitarget-directed ligands for the treatment of Alzheimer's disease: Design, synthesis, and biological evaluation.新型脱氧瓦西酮衍生物作为治疗阿尔茨海默病的有效多靶点导向配体：设计、合成及生物学评价
Eur J Med Chem. 2017 Nov 10;140:118-127. doi: 10.1016/j.ejmech.2017.09.008. Epub 2017 Sep 8.
2
Comparison of oxidative aromatic coupling and the Scholl reaction.氧化偶联芳香族反应与施罗尔反应的比较。
Angew Chem Int Ed Engl. 2013 Sep 16;52(38):9900-30. doi: 10.1002/anie.201210238. Epub 2013 Jul 14.
3
Selective copper(II) acetate and potassium iodide catalyzed oxidation of aminals to dihydroquinazoline and quinazolinone alkaloids.
选择性铜(II)醋酸盐和碘化钾催化的脒到二氢喹唑啉和喹唑啉酮生物碱的氧化反应。
Beilstein J Org Chem. 2013 Jun 20;9:1194-201. doi: 10.3762/bjoc.9.135. Print 2013.
4
Synthesis of some new tricyclic 4(3H)-quinazolinone derivatives.一些新型三环4(3H)-喹唑啉酮衍生物的合成。
Res Pharm Sci. 2011 Jul;6(2):93-100.
5
iotbx.cif: a comprehensive CIF toolbox.iotbx.cif：一个全面的CIF工具箱。
J Appl Crystallogr. 2011 Dec 1;44(Pt 6):1259-1263. doi: 10.1107/S0021889811041161. Epub 2011 Oct 29.
6
Atroposelective total synthesis of axially chiral biaryl natural products.轴手性联芳基天然产物的对映选择性全合成。
Chem Rev. 2011 Feb 9;111(2):563-639. doi: 10.1021/cr100155e. Epub 2010 Oct 12.
7
Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling.通过不对称联芳偶联反应的全合成手性联芳天然产物。
Chem Soc Rev. 2009 Nov;38(11):3193-207. doi: 10.1039/b821092f. Epub 2009 Sep 23.
8
One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine.简单生物碱的一锅法合成：2,3-聚亚甲基-4(3H)-喹唑啉酮、路脱宁A、色胺酮和吴茱萸次碱。
Chem Pharm Bull (Tokyo). 2008 Apr;56(4):607-9. doi: 10.1248/cpb.56.607.
9
A short history of SHELX.SHELX简史。
Acta Crystallogr A. 2008 Jan;64(Pt 1):112-22. doi: 10.1107/S0108767307043930. Epub 2007 Dec 21.
10
Anti-ulcer activity of Adhatoda vasica Nees.鸭嘴花的抗溃疡活性。
J Herb Pharmacother. 2006;6(2):43-9.