Modular synthesis of mono, di, and tri-1,4-disubstituted-1,2,3-triazoles through copper-mediated alkyne-azide cycloaddition

被引：23

作者：

Stefani, Helio A. ^{[1
]}

Canduzini, Hugo A. ^{[1
]}

Manarin, Flavia ^{[1
]}

机构：

[1] Univ Sao Paulo, Dept Farm, Fac Ciencias Farmaceut, BR-05508 Sao Paulo, Brazil

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 46期

基金：

巴西圣保罗研究基金会;

关键词：

Click chemistry; 1,2,3-Triazole; Cycloaddition; Propargyl alcohol; Ultrasound; CLICK-CHEMISTRY; ANTIMICROBIAL ACTIVITY; TERMINAL ALKYNES; WATER; ACID;

D O I：

10.1016/j.tetlet.2011.09.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 1,2,3-triazoles was developed employing sequential copper azide-alkyne cycloaddition, tosylation, sodium azide, and copper azide-alkyne steps. This approach allowed the synthesis of two and three 1,2,3-triazole rings. A preliminary study to gain further insight into the reaction was performed using in situ ReactIR technology. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6086 / 6090

页数：5

共 28 条

[1] "Click" Synthesis of Nonsymmetrical Bis(1,2,3-triazoles)
Aizpurua, Jesus M.
Azcune, Itxaso
Fratila, Raluca M.
Balentova, Eva
Sagartzazu-Aizpurua, Maialen
Miranda, Jose I.
[J]. ORGANIC LETTERS, 2010, 12 (07) : 1584 - 1587
[2] Base dependence in copper-catalyzed Huisgen reactions: Efficient formation of bistriazoles
Angell, Yu
Burgess, Kevin
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (20) : 3649 - 3651
[3] 'Click' chemistry in polymer and materials science
Binder, Wolfgang H.
Sachsenhofer, Robert
[J]. MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (01) : 15 - 54
[4] Synthesis of Unsymmetrical 1,1′-Disubstituted Bis(1,2,3-triazole)s Using Monosilylbutadiynes
Doak, Bradley C.
Scanlon, Martin J.
Simpson, Jamie S.
[J]. ORGANIC LETTERS, 2011, 13 (03) : 537 - 539
[5] Aza cope rearrangement of propargyl enammonium cations catalyzed by a self-assembled "nanozyme"
Hastings, Courtney J.
Fiedler, Dorothea
Bergman, Robert G.
Raymond, Kenneth N.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (33) : 10977 - 10983
[6] Synthesis, characterization and antimicrobial activity of some substituted 1,2,3-triazoles
Holla, BS
Mahalinga, M
Karthikeyan, MS
Poojary, B
Akberali, PM
Kumari, NS
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (11) : 1173 - 1178
[7] On the nature of rate acceleration in the synthesis and fragmentation of triazolines by Bronsted acid: Secondary catalysis by water (hydronium triflate)
Hong, Ki Bum
Donahue, Matthew G.
Johnston, Jeffrey N.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (07) : 2323 - 2328
[8] HUISGEN R, 1984, 3 DIPOLAR CYCLOADDIT, P1
[9] Palladium(II) Complexes of Readily Functionalized Bidentate 2-Pyridyl-1,2,3-triazole "Click" Ligands: A Synthetic, Structural, Spectroscopic, and Computational Study
Kilpin, Kelly J.
Gavey, Emma L.
McAdam, C. John
Anderson, Christopher B.
Lind, Samuel J.
Keep, Courtney C.
Gordon, Keith C.
Crowley, James D.
[J]. INORGANIC CHEMISTRY, 2011, 50 (13) : 6334 - 6346
[10] The growing impact of click chemistry on drug discovery
Kolb, HC
Sharpless, KB
[J]. DRUG DISCOVERY TODAY, 2003, 8 (24) : 1128 - 1137

← 1 2 3 →