Visible-light-promoted three-component cycloaddition reaction: synthesis of 4-functionalized 1,5-disubstituted 1,2,3-triazoles

被引:8
作者
Kumar, Atul [1 ]
Kumar, Navaneet [1 ,2 ]
Bhadoria, Deepak [1 ,2 ]
机构
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Sect 10,Sitapur Rd,POB 173 Lucknow, Lucknow 226031, Uttar Pradesh, India
[2] Acad Sci & Innovat Res, Ghaziabad 201002, India
关键词
AZIDE-ALKYNE CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; CATALYZED CYCLOADDITION; TERMINAL ALKYNES; DIRECT ACCESS; IODINE; CYCLIZATION; SULFONES;
D O I
10.1039/d1gc02328d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first visible-light promoted and photocatalyst-free three-component reaction protocol has been developed to synthesize 4-functionalized 1,5-disubstituted 1,2,3-triazoles from terminal alkynes, aryl azides, and arylsulfinic acid sodium salts or arylsulfonyl hydrazides in an aqueous medium at room temperature. Notably, the reaction proceeds seamlessly without using any transition-metal catalysts, ligands, or photocatalysts, and also reduces chemical waste. It also features an easy operation procedure, high regioselectivity, scalability, a broad substrate scope, mild reaction conditions, and good functional group tolerance.
引用
收藏
页码:7987 / 7995
页数:9
相关论文
共 110 条
  • [1] Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles
    Ackermann, Lutz
    Jeyachandran, Rajkumar
    Potukuchi, Harish K.
    Novak, Petr
    Buettner, Lea
    [J]. ORGANIC LETTERS, 2010, 12 (09) : 2056 - 2059
  • [2] Catalytic Direct Arylations in Polyethylene Glycol (PEG): Recyclable Palladium(0) Catalyst for C-H Bond Cleavages in the Presence of Air
    Ackermann, Lutz
    Vicente, Ruben
    [J]. ORGANIC LETTERS, 2009, 11 (21) : 4922 - 4925
  • [3] Click Chemistry: 1,2,3-Triazoles as Pharmacophores
    Agalave, Sandip G.
    Maujan, Suleman R.
    Pore, Vandana S.
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2696 - 2718
  • [4] In Vitro and in Vivo Evaluation of Fully Substituted (5-(3-Ethoxy-3-oxopropynyl)-4-(ethoxycarbonyl)-1,2,3-triazolyl-glycosides as Original Nucleoside Analogues to Circumvent Resistance in Myeloid Malignancies
    Amdouni, Hella
    Robert, Guillaume
    Driowya, Mohsine
    Furstoss, Nathan
    Metier, Camille
    Dubois, Alix
    Dufies, Maeva
    Zerhouni, Marwa
    Orange, Francois
    Lacas-Gervais, Sandra
    Bougrin, Khalid
    Martin, Anthony R.
    Auberger, Patrick
    Benhida, Rachid
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (04) : 1523 - 1533
  • [5] [Anonymous], 1984, 1 3 DIPOLAR CYCLOADD
  • [6] Regioselective Intermolecular Sulfur-Oxygen Difunctionalization (Phenoxysulfonylation) of Alkynes: One-Pot Construction of (Z)-β-Phenoxy Vinylsulfones
    Ansari, Mohd Yeshab
    Kumar, Navaneet
    Kumar, Atul
    [J]. ORGANIC LETTERS, 2019, 21 (11) : 3931 - 3936
  • [7] The Rich Chemistry Resulting from the 1,3-Dipolar Cycloaddition Reactions of Enamines and Azides
    Bakulev, Vasiliy A.
    Beryozkina, Tetyana
    Thomas, Joice
    Dehaen, Wim
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (03) : 262 - 294
  • [8] Cooperative Light-Activated Iodine and Photoredox Catalysis for the Amination of Csp3-H Bonds
    Becker, Peter
    Duhamel, Thomas
    Stein, Christopher J.
    Reiher, Markus
    Muniz, Kilian
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (27) : 8004 - 8008
  • [9] Organocatalytic Synthesis of 1,2,3-Triazoles from Unactivated Ketones and Arylazides
    Belkheira, Mokhtaria
    El Abed, Douniazad
    Pons, Jean-Marc
    Bressy, Cyril
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (46) : 12917 - 12921
  • [10] Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism
    Boren, Brant C.
    Narayan, Sridhar
    Rasmussen, Lars K.
    Zhang, Li
    Zhao, Haitao
    Lin, Zhenyang
    Jia, Guochen
    Fokin, Valery V.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) : 8923 - 8930