• 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

通过连续的炔丙基化/羟基化苯并环化反应一锅法合成3-羟基咔唑

One-Pot Assembly of 3-Hydroxycarbazoles via Uninterrupted Propargylation/Hydroxylative Benzannulation Reactions.

作者信息

Raji Reddy Chada, Subbarao Muppidi, Sathish Puppala, Kolgave Dattahari H, Donthiri Ramachandra Reddy

机构信息

Department of Organic Synthesis & Process Chemistry , CSIR-Indian Institute of Chemical Technology , Hyderabad 500007 , India.

Academy of Scientific and Innovative Research (AcSIR) , Ghaziabad 201 002 , India.

出版信息

Org Lett. 2020 Jan 17;22(2):689-693. doi: 10.1021/acs.orglett.9b04472. Epub 2020 Jan 7.

DOI:10.1021/acs.orglett.9b04472
PMID:31909623
Abstract

A novel strategy for the synthesis of 3-hydroxycarbazoles involving the consecutive propargylation/palladium-catalyzed hydroxylative benzannulation of indole-2-carbonyls with propargylic alcohols has been exploited. This one-pot procedure leads to a wide range of substituted 3-hydroxycarbazoles in high yield with a broad substrate scope. The method was further extended to access furano-carbazole derivatives from dialkynols via tandem annulations.

摘要

一种用于合成3-羟基咔唑的新策略已被开发出来,该策略涉及吲哚-2-羰基与炔丙醇的连续炔丙基化/钯催化的羟基化苯并环化反应。这种一锅法能以高收率得到多种取代的3-羟基咔唑,底物范围广泛。该方法还通过串联环化进一步扩展到从二醇炔合成呋喃并咔唑衍生物。

相似文献

1
One-Pot Assembly of 3-Hydroxycarbazoles via Uninterrupted Propargylation/Hydroxylative Benzannulation Reactions.通过连续的炔丙基化/羟基化苯并环化反应一锅法合成3-羟基咔唑
Org Lett. 2020 Jan 17;22(2):689-693. doi: 10.1021/acs.orglett.9b04472. Epub 2020 Jan 7.
2
One-Pot Sequential Propargylation/Cycloisomerization: A Facile [4+2]-Benzannulation Approach to Carbazoles.一锅法顺序炔丙基化/环异构化:一种简便的咔唑[4+2]苯并环化方法。
Chemistry. 2016 Feb 12;22(7):2501-6. doi: 10.1002/chem.201503496. Epub 2016 Jan 14.
3
[4 + 2] Benzannulation of 3-Alkenylpyrroles/Thiophenes with Propargylic Alcohols: Access to Substituted Indoles, Benzothiophenes, and Aza[5]helicenes.[4 + 2]芳构化反应:3-烯基吡咯/噻吩与丙炔醇的反应,可得到取代吲哚、苯并噻吩和氮杂[5]薁。
J Org Chem. 2017 Mar 3;82(5):2345-2354. doi: 10.1021/acs.joc.6b02637. Epub 2017 Feb 22.
4
Brønsted acid-catalyzed propargylation/cycloisomerization tandem reaction: one-pot synthesis of substituted oxazoles from propargylic alcohols and amides.布朗斯特酸催化的炔丙基化/环异构化串联反应:由炔丙醇和酰胺一锅法合成取代恶唑
J Org Chem. 2009 Apr 17;74(8):3148-51. doi: 10.1021/jo8027533.
5
An atom- and pot-economical consecutive multi-step reaction approach to polycyclic aromatic hydrocarbons (PAHs).一种用于多环芳烃(PAHs)的原子和试剂经济的连续多步反应方法。
Chem Commun (Camb). 2017 Feb 2;53(11):1904-1907. doi: 10.1039/c6cc09108c.
6
Electrophilic chemistry of propargylic alcohols in imidazolium ionic liquids: propargylation of arenes and synthesis of propargylic ethers catalyzed by metallic triflates [Bi(OTf)3, Sc(OTf)3, Yb(OTf)3], TfOH, or B(C6F5)3.在咪唑鎓离子液体中丙炔醇的亲电化学:三氟甲磺酸铋[Bi(OTf)3、三氟甲磺酸钪[Sc(OTf)3]、三氟甲磺酸镱[Yb(OTf)3]、三氟甲磺酸[TfOH]或三氟化硼[B(C6F5)3]催化的芳基丙炔化和丙炔醚合成。
Org Biomol Chem. 2011 Apr 7;9(7):2518-29. doi: 10.1039/c0ob00872a. Epub 2011 Feb 21.
7
Metal-free propargylation/aza-annulation approach to substituted β-carbolines and evaluation of their photophysical properties.无金属炔丙基化/氮杂环化方法合成取代β-咔啉及其光物理性质的评价。
Org Biomol Chem. 2019 Oct 30;17(42):9291-9304. doi: 10.1039/c9ob01959f.
8
Synthesis of Carbazoles and Carbazole-Containing Heterocycles via Rhodium-Catalyzed Tandem Carbonylative Benzannulations.通过铑催化的串联羰基化苯并环化反应合成咔唑及含咔唑杂环化合物。
J Org Chem. 2016 Apr 1;81(7):2930-42. doi: 10.1021/acs.joc.6b00212. Epub 2016 Mar 21.
9
Palladium-Catalyzed Cascade Decarboxylative Amination/6- Benzannulation of -Alkynylarylketones with -Hydroxyamides To Access Diverse 1-Naphthylamine Derivatives.钯催化的α-炔基芳基酮与α-羟基酰胺的级联脱羧胺化/6-苯并环化反应合成多样的1-萘胺衍生物
Org Lett. 2020 May 15;22(10):3890-3894. doi: 10.1021/acs.orglett.0c01183. Epub 2020 May 4.
10
One-pot synthesis of substituted furans using Cu(OTf)(2)-catalyzed propargylation/cycloisomerization tandem reaction.使用Cu(OTf)₂催化的炔丙基化/环异构化串联反应一锅法合成取代呋喃。
J Comb Chem. 2009 Jan-Feb;11(1):103-9. doi: 10.1021/cc8001316.

引用本文的文献

1
Recent Advances in the Synthesis of Propargyl Derivatives, and Their Application as Synthetic Intermediates and Building Blocks.炔丙基衍生物的合成进展及其作为合成中间体和构建块的应用。
Molecules. 2023 Apr 11;28(8):3379. doi: 10.3390/molecules28083379.
2
Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor-Acceptor Cyclopropanes.通过给体-受体环丙烷的发散级联反应合成咔唑和二氢咔唑。
Org Lett. 2021 Oct 1;23(19):7592-7596. doi: 10.1021/acs.orglett.1c02795. Epub 2021 Sep 20.
3
Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction.
通过转移的 Bischler-Napieralski 级联反应合成咔唑。
Org Lett. 2021 Apr 16;23(8):3100-3104. doi: 10.1021/acs.orglett.1c00785. Epub 2021 Mar 31.
4
Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation.通过涉及炔烃环化的一锅法反应构建多环天然产物骨架的最新进展
Front Chem. 2020 Oct 15;8:580355. doi: 10.3389/fchem.2020.580355. eCollection 2020.