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

被引:9
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 [J].
Ackermann, Lutz ;
Jeyachandran, Rajkumar ;
Potukuchi, Harish K. ;
Novak, Petr ;
Buettner, Lea .
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 [J].
Ackermann, Lutz ;
Vicente, Ruben .
ORGANIC LETTERS, 2009, 11 (21) :4922-4925
[3]   Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].
Agalave, Sandip G. ;
Maujan, Suleman R. ;
Pore, Vandana S. .
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 [J].
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 .
JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (04) :1523-1533
[5]   Regioselective Intermolecular Sulfur-Oxygen Difunctionalization (Phenoxysulfonylation) of Alkynes: One-Pot Construction of (Z)-β-Phenoxy Vinylsulfones [J].
Ansari, Mohd Yeshab ;
Kumar, Navaneet ;
Kumar, Atul .
ORGANIC LETTERS, 2019, 21 (11) :3931-3936
[6]   The Rich Chemistry Resulting from the 1,3-Dipolar Cycloaddition Reactions of Enamines and Azides [J].
Bakulev, Vasiliy A. ;
Beryozkina, Tetyana ;
Thomas, Joice ;
Dehaen, Wim .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (03) :262-294
[7]   Cooperative Light-Activated Iodine and Photoredox Catalysis for the Amination of Csp3-H Bonds [J].
Becker, Peter ;
Duhamel, Thomas ;
Stein, Christopher J. ;
Reiher, Markus ;
Muniz, Kilian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (27) :8004-8008
[8]   Organocatalytic Synthesis of 1,2,3-Triazoles from Unactivated Ketones and Arylazides [J].
Belkheira, Mokhtaria ;
El Abed, Douniazad ;
Pons, Jean-Marc ;
Bressy, Cyril .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (46) :12917-12921
[9]   Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism [J].
Boren, Brant C. ;
Narayan, Sridhar ;
Rasmussen, Lars K. ;
Zhang, Li ;
Zhao, Haitao ;
Lin, Zhenyang ;
Jia, Guochen ;
Fokin, Valery V. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) :8923-8930
[10]   Metal-Free Sulfonylation of 3,4-Dihalo-2(5H)-furanones (X = Cl, Br) with Sodium Sulfinates under Air Atmosphere in Aqueous Media via a Radical Pathway [J].
Cao, Liang ;
Li, Jian-Xiao ;
Wu, Han-Qing ;
Jiang, Kai ;
Hao, Zhi-Feng ;
Luo, Shi-He ;
Wang, Zhao-Yang .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (03) :4147-4153