One-Pot Synthesis of 1,4-Disubstituted Pyrazoles from Arylglycines via Copper-Catalyzed Sydnone-Alkyne Cycloaddition Reaction

被引：73
|
作者：
Specklin, Simon [1 ]
Decuypere, Elodie [1 ]
Plougastel, Lucie [1 ]
Aliani, Soifia [1 ]
Taran, Frederic [1 ]
机构：
[1] CEA, Serv Chim Bioorgan & Marquage, IBiTecS, F-91191 Gif Sur Yvette, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 16期
关键词：
REGIOSELECTIVE SYNTHESIS; N-ARYLGLYCINES; NANO2/AC2O;
D O I：
10.1021/jo501420r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A robust method for constructing 1,4-pyrazoles from arylglycines was developed using the copper-catalyzed sydnone-alkyne cycloaddition reaction. The procedure offers a straightforward and general route to the pyrazole heterocycle through a three-step one-pot procedure.
引用
收藏
页码：7772 / 7777
页数：6
相关论文
共 50 条
  • [1] One-pot strategy of copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles
    Xie, Caixia
    Han, Xushuang
    Gong, Jian
    Li, Danyang
    Ma, Chen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (27) : 5811 - 5819
  • [2] One-pot copper-catalyzed synthesis of N-functionalized pyrazoles from boronic acids
    Beveridge, Ramsay E.
    Fernando, Dilinie
    Gerstenberger, Brian S.
    TETRAHEDRON LETTERS, 2010, 51 (38) : 5005 - 5008
  • [3] Copper-catalyzed one-pot synthesis of 1,4-benzothiazine-3-ones
    Zhang, Lingyu
    Zhang, Songlin
    TETRAHEDRON LETTERS, 2023, 130
  • [4] Continuous metal scavenging and coupling to one-pot copper-catalyzed azide-alkyne cycloaddition click reaction in flow
    Noël, Timothy (t.noel@tue.nl), 1600, Elsevier B.V., Netherlands (270):
  • [5] Continuous metal scavenging and coupling to one-pot copper-catalyzed azide-alkyne cycloaddition click reaction in flow
    Gursel, Iris Vural
    Aldiansyah, Ferry
    Wang, Qi
    Noel, Timothy
    Hessel, Volker
    CHEMICAL ENGINEERING JOURNAL, 2015, 270 : 468 - 475
  • [6] One-pot synthesis of enantiomerically enriched 2,3-disubstituted cyclopentanones via copper-catalyzed 1,4-reduction and alkylation
    Yun, J
    Buchwald, SL
    ORGANIC LETTERS, 2001, 3 (08) : 1129 - 1131
  • [7] Copper-Catalyzed One-Pot Multicomponent Reactions: Synthesis of 4-Arylsulfenyl Pyrazoles
    Oliveira, Daniela H.
    Alves, Diego
    Jacob, Raquel G.
    Xavier, Maurcio C. D. F.
    CURRENT ORGANIC SYNTHESIS, 2015, 12 (06) : 822 - 829
  • [8] A New Insight Into The Huisgen Reaction: Heterogeneous Copper Catalyzed Azide-Alkyne Cycloaddition for the Synthesis of 1,4-Disubstituted Triazole (From 2018-2023)
    Kasana, Shivani
    Nigam, Vaibhav
    Singh, Surbhi
    Kurmi, Balak Das
    Patel, Preeti
    CHEMISTRY & BIODIVERSITY, 2024, 21 (06)
  • [9] Cu(I)-catalyzed one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles via nucleophilic displacement and 1,3-dipolar cycloaddition
    Sreedhar, B
    Reddy, PS
    Kumar, NS
    TETRAHEDRON LETTERS, 2006, 47 (18) : 3055 - 3058
  • [10] One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from nitrobenzenes
    Fen Zhao
    Zhen Chen
    Kai Xie
    Rui Yang
    Yu-Bo Jiang
    ChineseChemicalLetters, 2016, 27 (01) : 109 - 113
12345