A convenient protocol for a zinc-catalysed synthesis of electron-poor indoles

被引:0
|
作者
Medici, F. [1 ]
Montinari, F. [1 ]
Donato, E. [1 ]
Raimondi, L. [1 ]
Benaglia, M. [1 ]
机构
[1] Univ Milan, Chem Dept, Via Camillo Golgi 19, I-20133 Milan, Italy
关键词
Indole; Cyclisation; Zinc; API precursor; Alkynyl group; 2-ALKYNYLANILINES; SCAFFOLD;
D O I
10.1016/j.tetlet.2023.154340
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient catalytic protocol for the synthesis of electron-poor indoles was envisioned. A cyclisation reaction of electron-deficient 2-(alkynyl)-anilines, catalysed by Zn(II) salts, was successfully developed and applied to the synthesis of an API precursor. A two-step one-pot procedure starting from aniline derivatives was successfully developed. The use of a readily available, non-noble metal further enhanced the value of the protocol. (c) 2023 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 50 条
  • [21] Nitronyl Nitroxide Bifunctionalized Electron-Poor Chromophores: Synthesis of Stable Dye Biradicals by Lewis Acid Promoted Desilylation
    Rausch, Rodger
    Krause, Ana-Maria
    Krummenacher, Ivo
    Braunschweig, Holger
    Wuerthner, Frank
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (03): : 2447 - 2457
  • [22] Electron-Poor Bowl-Shaped Polycyclic Aromatic Dicarboximides: Synthesis, Crystal Structures, and Optical and Redox Properties
    Shoyama, Kazutaka
    Schmidt, David
    Mahl, Magnus
    Wuerthner, Frank
    ORGANIC LETTERS, 2017, 19 (19) : 5328 - 5331
  • [23] Synthesis, Structure, and Bonding of BaTl4. Size Effects on Encapsulation of Cations in Electron-Poor Metal Networks
    Dai, Jing-Cao
    Gupta, Shalabh
    Corbett, John D.
    INORGANIC CHEMISTRY, 2011, 50 (01) : 238 - 244
  • [24] Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton - Electron-poor pyrroles exhibit dramatically reduced nucleophilicity
    Beshara, Cory S.
    Pearce, Beth M.
    Thompson, Alison
    CANADIAN JOURNAL OF CHEMISTRY, 2008, 86 (10) : 951 - 957
  • [25] SYNTHESIS AND REACTIVITY OF ELECTRON-POOR 2-AZADIENES - [4+2] CYCLOADDITION REACTIONS WITH ALKENES AND ENAMINES
    PALACIOS, F
    DEHEREDIA, IP
    RUBIALES, G
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08): : 2384 - 2390
  • [26] A simple protocol for the michael addition of indoles with electron deficient olefins catalysed by TBAHS in aqueous media and their broad spectrum antibacterial activity
    M. Damodiran
    R. Senthil Kumar
    P. M. Sivakumar
    Mukesh Doble
    Paramasivan T. Perumal
    Journal of Chemical Sciences, 2009, 121
  • [27] A simple protocol for the michael addition of indoles with electron deficient olefins catalysed by TBAHS in aqueous media and their broad spectrum antibacterial activity
    Damodiran, M.
    Kumar, R. Senthil
    Sivakumar, P. M.
    Doble, Mukesh
    Perumal, Paramasivan T.
    JOURNAL OF CHEMICAL SCIENCES, 2009, 121 (01) : 65 - 73
  • [28] Three-component Synthesis of Electron-poor Alkenes using Isatin Derivatives, Acetylenic Esters, Triphenylphosphine and Theoretical Study
    Sheikhi, Masoome
    Sheikh, Davood
    Ramazani, Ali
    SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2014, 67 : 151 - 159
  • [29] Synthesis of electron-poor N-Vinylimidazole derivatives catalyzed by Silica nanoparticles under solvent-free conditions
    Ramazani, A.
    Farshadi, A.
    Mahyari, A.
    Sadri, F.
    Joo, S. Woo
    Asiabi, P. Azimzadeh
    Fardood, S. Taghavi
    Dayyani, N.
    Ahankar, H.
    INTERNATIONAL JOURNAL OF NANO DIMENSION, 2016, 7 (01) : 41 - 48
  • [30] Robust and Scalable Reductive Amination Protocol for Electron-Poor Heterocyclic Amines Using Et3 SiH/TFA as Reducing Agent
    Schafer, Gabriel
    Reber, Stefan
    Ahmetovic, Muhamed
    Fleischer, Tony
    Leuenberger, Daniel
    Blumer, Nicole
    Udry, Megan
    Abele, Stefan
    SYNTHESIS-STUTTGART, 2023, 55 (09): : 1328 - 1336