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
来源：
TETRAHEDRON LETTERS | 2023年 / 116卷
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
  • [31] [Ag(PcL)]-Catalyzed Domino Reactions of 2-Alkynylbenzaldehydes with Electron-Poor Anilines: Synthesis of 1-Aminoisochromenes
    Pirovano, Valentina
    Hamdan, Gabriele
    Garanzini, Davide
    Brambilla, Elisa
    Rossi, Elisabetta
    Caselli, Alessandro
    Abbiati, Giorgio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (17) : 2592 - 2599
  • [32] SYNTHESIS OF STABILIZED PHOSPHORUS YLIDES FROM ELECTRON-POOR ALCOHOLS AND THEIR APPLICATIONS IN THE PREPARATION OF 2,5-DIHYDROFURAN DERIVATIVES
    Salmanpour, Sadegh
    Ramazani, Ali
    Ahmadi, Yavar
    BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2012, 26 (01) : 153 - 158
  • [33] CHEMISTRY IN HETEROCYCLIC-COMPOUNDS SERIES .38. SYNTHESIS OF BIHETEROARYLS BY FACILE DECARBONYLATION OF ELECTRON-POOR HETEROAROMATIC KETONES
    NEWKOME, GR
    TAYLOR, HCR
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (08): : 1362 - 1363
  • [34] PALLADIUM- AND NORBORNENE-CATALYZED SYNTHESIS OF HIGHLY FUNCTIONALIZED THIOPHENES: THE REMARKABLE EFFECT OF ELECTRON-POOR OLEFINS AS LIGAND
    Della Ca, Nicola
    Motti, Elena
    Maestri, Giovanni
    Malacria, Max
    HETEROCYCLES, 2017, 95 (02) : 753 - 760
  • [35] Palladium-catalyzed selective synthesis of 3,4-dihydroquinazolines from electron-rich arylamines, electron-poor arylamines and glyoxalates
    Wu, Chao
    Wang, Jie
    Zhang, Xing-Yu
    Jia, Guo-Kai
    Cao, Zhong
    Tang, Zilong
    Yu, Xianyong
    Xu, Xinhua
    He, Wei-Min
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (27) : 5050 - 5054
  • [36] Synthesis of highly electron-poor alkenes from in situ generated stabilized phosphorus ylides and ninhydrin via intermolecular Wittig reaction
    Ramazani, A
    Bodaghi, A
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (08) : 1615 - 1620
  • [37] One-step synthesis of electron-poor alkenes from triphenylphosphine, acetylenic esters, 2,2,2-trichloroethanol, and ninhydrin
    Ramazani, Ali
    Azizian, Abbas
    Bandpey, Maryam
    Noshiranzadeh, Nader
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (12) : 2731 - 2734
  • [38] Synthesis, stability and reactivity of palladium(0) olefin complexes bearing labile or hemi-labile ancillary ligands and electron-poor olefins
    Canovese, Luciano
    Visentin, Fabiano
    INORGANICA CHIMICA ACTA, 2010, 363 (11) : 2375 - 2386
  • [39] ELECTRON-TRANSFER CATALYZED CARBONYL SUBSTITUTION .3. SYNTHESIS AND SPECTROSCOPY OF MONONUCLEAR AND DINUCLEAR CIS-PHOSPHANETETRACARBONYLTUNGSTEN(0) COMPLEXES OF ELECTRON-POOR PYRIDINES
    OLBRICHDEUSSNER, B
    KAIM, W
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 361 (03) : 335 - 351
  • [40] Palladium-Catalyzed Indole and Azaindole Synthesis by Direct Annulation of Electron-Poor o-Chloroanilines and o-Chloroaminopyridines with Aldehydes
    Xu, Zhengren
    Hu, Weimin
    Zhang, Fengying
    Li, Qingjiang
    Lue, Zhiyao
    Zhang, Lihe
    Jia, Yanxing
    SYNTHESIS-STUTTGART, 2008, 24 (24): : 3981 - 3987
12345