Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition

被引:70
|
作者
Harju, K
Vahermo, M
Mutikainen, I
Yli-Kauhaluoma, J
机构
[1] Univ Helsinki, Dept Pharm, Viikki Drug Discovery Technol Ctr, FIN-00014 Helsinki, Finland
[2] Univ Helsinki, Dept Chem, Inorgan Chem Lab, FIN-00014 Helsinki, Finland
来源
JOURNAL OF COMBINATORIAL CHEMISTRY | 2003年 / 5卷 / 06期
关键词
D O I
10.1021/cc030110c
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition of polymer-bound azides to various alkynes is reported. Polymer-bound azides were synthesized from polymer-bound halides and sodium azide and reacted with alkynes to produce polymer-bound 1,2,3-triazoles. Cleavage of the triazoles was performed with trifluoroacetic acid. A traceless synthesis of 1,2,3-triazoles was developed using 2-methoxy-substituted resin (polymer-bound 4-hydroxy-2-methoxybenzyl alcohol). In addition, a synthesis of 4-hydroxybenzyl-substituted 1,2,3-triazoles from the bromo-Wang resin (4-(bromomethyl)phenoxymethyl polystyrene) was achieved.
引用
收藏
页码:826 / 833
页数:8
相关论文
共 50 条
  • [1] Trimethylsilyl-directed 1,3-dipolar cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles
    Coats, SJ
    Link, JS
    Gauthier, D
    Hlasta, DJ
    [J]. ORGANIC LETTERS, 2005, 7 (08) : 1469 - 1472
  • [2] Synthesis of 1-(substituted benzyl)-1,2,3-triazoles by 1,3-dipolar cycloaddition reaction
    Hu, YH
    Liu, SL
    Tong, QY
    Huang, FR
    Shen, YJ
    Qi, HM
    Du, L
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (10) : 1228 - 1232
  • [3] 1,3-Dipolar Cycloaddition in the Synthesis of Novel Isoxazoline/Pyrazole Derivatives Bearing 1,2,3-Triazoles Moiety
    Zeng, Yongming
    Liu, Fangming
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (03) : 696 - 702
  • [4] Solid-phase synthesis of substituted 1,2,3-triazoles
    Zaragoza, F
    Petersen, SV
    [J]. TETRAHEDRON, 1996, 52 (32) : 10823 - 10826
  • [5] Regiospecific synthesis of 2-allyl-1,2,3-triazoles by palladium-catalyzed 1,3-dipolar cycloaddition
    Kamijo, S
    Jin, TN
    Huo, ZB
    Yamamoto, Y
    [J]. TETRAHEDRON LETTERS, 2002, 43 (52) : 9707 - 9710
  • [6] [3+2] cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles
    Gao, Yongnian
    Lam, Yulin
    [J]. ORGANIC LETTERS, 2006, 8 (15) : 3283 - 3285
  • [7] Solid-phase synthesis of functionalized 1,2,3-triazoles
    Blass, BE
    Coburn, KR
    Faulkner, AL
    Hunn, CL
    Natchus, MG
    Parker, MS
    Portlock, DE
    Tullis, JS
    Wood, R
    [J]. TETRAHEDRON LETTERS, 2002, 43 (22) : 4059 - 4061
  • [8] Solid-phase synthesis of functionalized tropane derivatives via 1,3-dipolar cycloaddition
    Caix-Haumesser, S
    Hanna, I
    Lallemand, JY
    Peyronel, JF
    [J]. TETRAHEDRON LETTERS, 2001, 42 (22) : 3721 - 3723
  • [9] Synthesis and cytotoxicity evaluation of novel 1,4-disubstituted 1,2,3-triazoles via CuI catalysed 1,3-dipolar cycloaddition
    Vantikommu, Jyothi
    Palle, Sadanandam
    Reddy, Punganuru Surendra
    Ramanatham, Vinodkumar
    Khagga, Mukkanti
    Pallapothula, Venkateswara Rao
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) : 5044 - 5050
  • [10] Synthesis of carbohydrate-derived 1,2,3-triazoles using 1,3-dipolar cycloaddition on a soluble polymer support
    Freeze, S
    Norris, P
    [J]. HETEROCYCLES, 1999, 51 (08) : 1807 - 1817