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
  • [1] The synthesis and characterization of electron-poor glycosylamines and derived glycosylamides
    Zyka, Jakub
    Prouza, Vit
    Habanova, Nina
    Pohl, Radek
    Parkan, Kamil
    CARBOHYDRATE RESEARCH, 2024, 536
  • [2] Synthesis of electron-poor hexa-peri-hexabenzocoronenes
    Jones, David J.
    Purushothaman, Balaji
    Ji, Shaomin
    Holmes, Andrew B.
    Wong, Wallace W. H.
    CHEMICAL COMMUNICATIONS, 2012, 48 (65) : 8066 - 8068
  • [3] Synthesis and reactivity of catalysts containing electron-poor bifunctional ligands
    Sattler, Daniel
    Rheingold, Arnold
    Grotjahn, Douglas
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [4] Solid acid-catalysed Michael-type conjugate addition of indoles to electron-poor C=C bonds: Towards high atom economical semicontinuous processes
    Bandini, M
    Fagioli, M
    Umani-Ronchi, A
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (05) : 545 - 548
  • [5] Michael addition of chloroalkyloxazolines to electron-poor alkenes: Synthesis of heterosubstituted cyclopropanes
    Rocchetti, MT
    Fino, V
    Capriati, V
    Florio, S
    Luisi, R
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04): : 1394 - 1400
  • [6] Synthesis, Structure, and Properties of the Electron-Poor II-V Semiconductor ZnAs
    Fischer, Andreas
    Eklof, Daniel
    Benson, Daryn E.
    Wu, Yang
    Scheidt, Ernst-Wilhelm
    Scherer, Wolfgang
    Haussermann, Ulrich
    INORGANIC CHEMISTRY, 2014, 53 (16) : 8691 - 8699
  • [7] Synthesis of perfluoroaryl sulfides at electron-poor arenes via an SNAr step with an unexpected mechanism
    Liao, Hsuan-Hung
    Lee, Shao-Chi
    Kao, Hsin
    Hsu, Yu-Ling
    Hsu, Che-Ming
    Tsao, Yong-Ting
    Minoza, Shinje
    Li, Li-Yun
    Tsai, Zong-Nan
    Chang, Kuei-Chen
    Cheng, Cheng-Ku
    Chan, Cheng-Lin
    Chien, Yi-Sian
    Chiu, Cheng-chau
    CELL REPORTS PHYSICAL SCIENCE, 2022, 3 (08):
  • [8] Synthesis, characterization, and crystal structures of molybdenum complexes of unsymmetrical electron-poor dithiolene ligands
    Mohapatra, Swagat K.
    Zhang, Yadong
    Sandhu, Bhupinder
    Fonari, Marina S.
    Timofeeva, Tatiana V.
    Marder, Seth R.
    Barlow, Stephen
    POLYHEDRON, 2016, 116 : 88 - 95
  • [9] Peptide Bioconjugates of Electron-Poor Metallocenes: Synthesis, Characterization, and Anti-Proliferative Activity
    Maschke, Marcus
    Grohmann, Jens
    Nierhaus, Claudia
    Lieb, Max
    Metzler-Nolte, Nils
    CHEMBIOCHEM, 2015, 16 (09) : 1333 - 1342
  • [10] Acylation of Electron-Poor Alkenyl Sulfoxides: Diverse Transformations for the Synthesis of Polysubstituted Phenols and Functionalized Carbocycles
    Li, Xiaoyu
    Zhang, Qianyun
    Xie, Yuanyuan
    Zhou, Hongwei
    SYNTHESIS-STUTTGART, 2023, 55 (17): : 2674 - 2682