Efficient one-pot synthesis of 1-aryl 1,2,3-triazoles from aryl halides and terminal alkynes in the presence of sodium azide

被引:78
作者
Andersen, J
Bolvig, S
Liang, XF
机构
[1] Leo Pharmaceut Prod, Dept Med Chem, DK-2750 Ballerup, Denmark
[2] Leo Pharmaceut Prod, Dept Spect & Phys Chem, DK-2750 Ballerup, Denmark
关键词
1,2,3-triazoles; one-pot; copper; 1,3-dipolar cycloaddition; catalyst;
D O I
10.1055/s-2005-921887
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient one-pot synthesis of 1-aryl 1,2,3-triazoles from aryl bromides/iodides and terminal alkynes in the presence of sodium azide is described. In the case of aryl iodides, the reactions proceeded at room temperature. The reactions normally gave high yields.
引用
收藏
页码:2941 / 2947
页数:7
相关论文
共 26 条
[1]   Rapid synthesis of aryl azides from aryl halides under mild conditions [J].
Andersen, J ;
Madsen, U ;
Björkling, F ;
Liang, XF .
SYNLETT, 2005, (14) :2209-2213
[2]   A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].
Appukkuttan, P ;
Dehaen, W ;
Fokin, VV ;
Van der Eycken, E .
ORGANIC LETTERS, 2004, 6 (23) :4223-4225
[3]   C2-symmetric macrocyclic carbohydrate/amino acid hybrids through copper(I)-catalyzed formation of 1,2,3-triazoles [J].
Billing, JF ;
Nilsson, UJ .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) :4847-4850
[4]   Applications of solid supported azide anion: a one-pot, two-step preparation of functionalized 1,2,3-triazoles [J].
Blass, BE ;
Coburn, KR ;
Faulkner, AL ;
Seibel, WL ;
Srivastava, A .
TETRAHEDRON LETTERS, 2003, 44 (10) :2153-2155
[5]   One-pot synthesis of triazole-linked glycoconjugates [J].
Chittaboina, S ;
Xie, F ;
Wang, Q .
TETRAHEDRON LETTERS, 2005, 46 (13) :2331-2336
[6]   Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by amino acid ligands [J].
Deng, W ;
Liu, L ;
Zhang, C ;
Liu, M ;
Guo, QX .
TETRAHEDRON LETTERS, 2005, 46 (43) :7295-7298
[7]   One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides [J].
Feldman, AK ;
Colasson, B ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (22) :3897-3899
[8]   Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition [J].
Harju, K ;
Vahermo, M ;
Mutikainen, I ;
Yli-Kauhaluoma, J .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (06) :826-833
[9]   Dendronized linear polymers via "click chemistry" [J].
Helms, B ;
Mynar, JL ;
Hawker, CJ ;
Fréchet, JMJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15020-15021
[10]   Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes [J].
Jin, T ;
Kamijo, S ;
Yamamoto, Y .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (18) :3789-3791