Synthesis of 3-(1H-1,2,3-Triazol-1-yl)-2-(arylselanyl)pyridines by Copper-Catalyzed 1,3-Dipolar Cycloaddition of 2-(Arylselanyl)-3-azido-pyridines with Terminal Alkynes

被引:9
作者
Schumacher, Ricardo F. [1 ]
Von Laer, Patrick B. [1 ]
Betin, Eduardo S. [1 ]
Cargnelutti, Roberta [1 ]
Perin, Gelson [1 ]
Alves, Diego [1 ]
机构
[1] Univ Fed Pelotas UFPel, CCQFA, LASOL, BR-96010900 Pelotas, RS, Brazil
关键词
selenium; pyridine; 1,2,3-triazoles; cycloaddition reactions; copper catalysis; ORGANOSELENIUM COMPOUNDS; CLICK CHEMISTRY; ENANTIOSELECTIVE ADDITION; BIOLOGICAL EVALUATION; SYN-ELIMINATION; SELENIUM; ARYLSELENIDES; DIETHYLZINC; SELENOXIDES; AGENTS;
D O I
10.5935/0103-5053.20150221
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We present here our results in the synthesis of eleven new 3-(1H-1,2,3-triazol-1-yl)-2-(arylselanyl)pyridines by copper-catalyzed azide-alkyne cycloaddition reactions. The reactions were performed in the presence of catalytic amount of copper(II) acetate and sodium ascorbate using a mixture of tetrahydrofuran/water (1:1) as solvent at room temperature in air. The reaction is tolerant to different functional groups such as substituted-benzene rings, alcohol and ester and none electronic or steric influence was observed. All the products were obtained in good to excellent yields. Alternatively to the conventional oil bath heating, the use of microwave irradiation or ultrasound methods is also presented as alternative energy sources.
引用
收藏
页码:2298 / 2306
页数:9
相关论文
共 59 条
  • [1] Alberto E. E., 2011, SELENIUM TELLURIUM C, P285
  • [2] Imidazolium ionic liquids containing selenium: synthesis and antimicrobial activity
    Alberto, Eduardo E.
    Rossato, Luana L.
    Alves, Sydney Hartz
    Alves, Diego
    Braga, Antonio L.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (04) : 1001 - 1003
  • [3] AlvarezBuilla J, 2011, MODERN HETEROCYCLIC CHEMISTRY, VOL 4, P1, DOI 10.1002/9783527637737
  • [4] Cu(I)-Catalyzed Huisgen Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry
    Amblard, Franck
    Cho, Jong Hyun
    Schinazi, Raymond F.
    [J]. CHEMICAL REVIEWS, 2009, 109 (09) : 4207 - 4220
  • [5] [Anonymous], 2015, Topics in Heterocyclic Chemistry.
  • [6] [Anonymous], 2007, FUNDAMENTALS HETEROC
  • [7] Microwave-assisted cycloaddition reactions
    Appukkuttan, Prasad
    Mehta, Vaibhav P.
    Van der Eycken, Erik V.
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (05) : 1467 - 1477
  • [8] Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes
    Braga, AL
    Paixao, MW
    LUdtke, DS
    Silveira, CC
    Rodrigues, OED
    [J]. ORGANIC LETTERS, 2003, 5 (15) : 2635 - 2638
  • [9] Efficient synthesis of chiral β-seleno amides via ring-opening reaction of 2-oxazolines and their application in the palladium-catalyzed asymmetric allylic alkylation
    Braga, AL
    Vargas, F
    Sehnem, JA
    Braga, RC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) : 9021 - 9024
  • [10] Seleno-imine: A new class of versatile, modular N,Se ligands for asymmetric palladium-catalyzed allylic alkylation
    Braga, AL
    Paixao, MW
    Marin, G
    [J]. SYNLETT, 2005, (11) : 1675 - 1678