• 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

卡宾催化由烯醛和2-甲基-3-氧代乙酸酯吲哚构建咔唑类化合物。

Carbene-Catalyzed Construction of Carbazoles from Enals and 2-Methyl-3-oxoacetate Indoles.

作者信息

Liu Dehai, Gao Yaru, Huang Jie, Fu Zhenqian, Huang Wei

机构信息

Key Laboratory of Flexible Electronics & Institute of Advanced Materials, Jiangsu National Synergetic Innovation Center for Advanced Materials , Nanjing Tech University , 30 South Puzhu Road , Nanjing 211816 , China.

Shaanxi Institute of Flexible Electronics (SIFE) , Northwestern Polytechnical University (NPU) , 127 West Youyi Road , Xi'an 710072 , China.

出版信息

J Org Chem. 2018 Nov 16;83(22):14210-14217. doi: 10.1021/acs.joc.8b02532. Epub 2018 Oct 30.

DOI:10.1021/acs.joc.8b02532
PMID:30351940
Abstract

Direct and rapid construction of carbazoles has been successfully developed via carbene-catalyzed oxidative formal [4 + 2] annulation of enals with 2-methyl-3-oxoacetate indoles. This metal-free reaction features a broad substrate scope, features good functional-group tolerance, proceeds under mild conditions, and can be easily scaled up.

摘要

通过卡宾催化的烯醛与2-甲基-3-氧代乙酸酯吲哚的氧化形式[4+2]环化反应,已成功开发出咔唑的直接快速构建方法。这种无金属反应具有广泛的底物范围,具有良好的官能团耐受性,在温和条件下进行,并且易于放大规模。

相似文献

1
Carbene-Catalyzed Construction of Carbazoles from Enals and 2-Methyl-3-oxoacetate Indoles.卡宾催化由烯醛和2-甲基-3-氧代乙酸酯吲哚构建咔唑类化合物。
J Org Chem. 2018 Nov 16;83(22):14210-14217. doi: 10.1021/acs.joc.8b02532. Epub 2018 Oct 30.
2
Access to Enantioenriched Spiro-ϵ-Lactam Oxindoles by an N-Heterocyclic Carbene-Catalyzed [4+3] Annulation of Flexible Oxotryptamines with Enals.通过氮杂环卡宾催化的柔性氧代色胺与烯醛的[4+3]环化反应获得对映体富集的螺-ε-内酰胺氧化吲哚。
Chemistry. 2019 Aug 27;25(48):11223-11227. doi: 10.1002/chem.201903144. Epub 2019 Aug 1.
3
Chiral N-Heterocyclic-Carbene-Catalyzed Cascade Asymmetric Desymmetrization of Cyclopentenediones with Enals: Access to Optically Active 1,3-Indandione Derivatives.手性 N-杂环卡宾催化环戊二酮与烯醛的串联不对称去对称化反应:合成光学活性 1,3-茚二酮衍生物
Org Lett. 2019 Nov 1;21(21):8582-8586. doi: 10.1021/acs.orglett.9b03178. Epub 2019 Oct 16.
4
Facile Synthesis of Polysubstituted Indolizines via One-Pot Reaction of 1-Acetylaryl 2-Formylpyrroles and Enals.通过1-乙酰基芳基2-甲酰基吡咯与烯醛的一锅反应简便合成多取代中氮茚。
Chem Asian J. 2020 Feb 3;15(3):352-355. doi: 10.1002/asia.201901517. Epub 2019 Dec 27.
5
Rhodium(III)-catalyzed C-H activation and intermolecular annulation with terminal alkynes: from indoles to carbazoles.铑(III)催化的C-H活化与末端炔烃的分子间环化反应:从吲哚到咔唑
Chem Commun (Camb). 2015 Feb 18;51(14):2925-8. doi: 10.1039/c4cc09823d.
6
Enantioselective synthesis of spiro γ-butyrolactones by N-heterocyclic carbene (NHC)-catalyzed formal [3 + 2] annulation of enals with 3-hydroxy oxindoles.通过N-杂环卡宾(NHC)催化烯醛与3-羟基氧化吲哚的形式[3 + 2]环化反应对映选择性合成螺γ-丁内酯。
Org Biomol Chem. 2017 Mar 1;15(9):2013-2019. doi: 10.1039/c7ob00148g.
7
Asymmetric Synthesis of 4-Aryl-3,4-dihydrocoumarins by N-Heterocyclic Carbene Catalyzed Annulation of Phenols with Enals.N-杂环卡宾催化酚与烯醛的环加成反应不对称合成 4-芳基-3,4-二氢香豆素
Org Lett. 2017 Mar 17;19(6):1318-1321. doi: 10.1021/acs.orglett.7b00088. Epub 2017 Feb 24.
8
N-Heterocyclic carbene-catalyzed [4+2] annulation of β-methyl enals and cyclic trifluoromethyl ketimines for the asymmetric synthesis of dihydroquinazolinone derivatives.N-杂环卡宾催化β-甲基烯醛与环状三氟甲基酮亚胺的[4+2]环化反应用于二氢喹唑啉酮衍生物的不对称合成
Chem Commun (Camb). 2017 Oct 12;53(82):11342-11344. doi: 10.1039/c7cc06562k.
9
Direct access to substituted benzo[b]carbazoles through cascade annulation of 2-vinylbenzaldehydes with indoles.通过 2-乙烯基苯甲醛与吲哚的级联环化反应直接获得取代苯并[b]咔唑。
Chem Commun (Camb). 2019 Mar 14;55(23):3339-3342. doi: 10.1039/c8cc10253h.
10
Enantioselective Synthesis of Spirocyclohexadienones by NHC-Catalyzed Formal [3+3] Annulation Reaction of Enals.手性 N-杂环卡宾催化的烯醛的形式 [3+3] 环加成反应构建螺环环己二烯酮
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):268-72. doi: 10.1002/anie.201507802. Epub 2015 Oct 21.

引用本文的文献

1
Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review.用于合成含氮杂环骨架的无金属催化剂的最新进展:聚焦于五元环和六元环的综述
RSC Adv. 2025 Mar 31;15(13):9676-9755. doi: 10.1039/d5ra00962f. eCollection 2025 Mar 28.
2
Photochemistry of 1-Phenyl-1-diazopropane and Its Diazirine Isomer: A CASSCF and MS-CASPT2 Study.1-苯基-1-重氮丙烷及其二氮杂环丙烯异构体的光化学:一项CASSCF和MS-CASPT2研究
J Phys Chem A. 2022 Nov 17;126(45):8372-8379. doi: 10.1021/acs.jpca.2c04816. Epub 2022 Nov 6.
3
Oxidative N-Heterocyclic Carbene Catalysis.
氧化氮杂环卡宾催化
Chemistry. 2023 Jan 18;29(4):e202202467. doi: 10.1002/chem.202202467. Epub 2022 Nov 22.
4
Synthesis of polysubstituted arenes through organocatalytic benzannulation.通过有机催化苯环化反应合成多取代芳烃。
RSC Adv. 2020 Nov 10;10(67):40983-41003. doi: 10.1039/d0ra08068c. eCollection 2020 Nov 9.
5
Organocatalytic asymmetric N-sulfonyl amide C-N bond activation to access axially chiral biaryl amino acids.有机催化不对称 N-磺酰酰胺 C-N 键活化用于构建轴手性联芳基氨基酸。
Nat Commun. 2020 Feb 19;11(1):946. doi: 10.1038/s41467-020-14799-8.