A new solvent system for efficient synthesis of 1,2,3-triazoles

被引：161

作者：

Lee, Bo-Young ^{[1
]}

Park, So Ra ^{[1
]}

Jeon, Heung Bae ^{[1
]}

Kim, Kwan Soo ^{[1
]}

机构：

[1] Yonsei Univ, Dept Chem, Ctr Bioact Mol Hybrids, Seoul 120749, South Korea

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 29期

关键词：

D O I：

10.1016/j.tetlet.2006.05.079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of CH2O2 as a co-solvent with H2O in the copper(l) -catalyzed 1,3-dipolar cycloaddition of organic azides and alkynes increased reaction rates and provided the corresponding 1,2,3-triazoles in excellent yields compared to other organic co-solvent systems. Moreover, we applied this discovery to prepare the functional multivalent compound in an excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5105 / 5109

页数：5

共 30 条

[1]

Alvarez R., 1994, J MED CHEM, V37, P4194

[2] 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

[3] Highly convergent synthesis of C3- or C2-symmetric carbohydrate macrocycles [J].

Bodine, KD ;

Gin, DY ;

Gin, MS .

ORGANIC LETTERS, 2005, 7 (20) :4479-4482

[4] Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide [J].

Bodine, KD ;

Gin, DY ;

Gin, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1638-1639

[5] Azide-alkyne coupling:: A powerful reaction for bioconjugate chemistry [J].

Breinbauer, R ;

Köhn, M .

CHEMBIOCHEM, 2003, 4 (11) :1147-1149

[6] STUDIES ON 1,2,3-TRIAZOLES .13. (PIPERAZINYLALKOXY)[1]BENZOPYRANO[2,3-D]-1,2,3-TRIAZOL-9(1H)-ONES WITH COMBINED H-1 ANTIHISTAMINE AND MAST-CELL STABILIZING PROPERTIES [J].

BUCKLE, DR ;

ROCKELL, CJM ;

SMITH, H ;

SPICER, BA .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2262-2267

[7] Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].

Chan, TR ;

Hilgraf, R ;

Sharpless, KB ;

Fokin, VV .

ORGANIC LETTERS, 2004, 6 (17) :2853-2855

[8] Clicking functionality onto electrode surfaces [J].

Collman, JP ;

Devaraj, NK ;

Chidsey, CED .

LANGMUIR, 2004, 20 (04) :1051-1053

[9] Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae [J].

Deiters, A ;

Cropp, TA ;

Mukherji, M ;

Chin, JW ;

Anderson, JC ;

Schultz, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11782-11783

[10] Click chemistry in materials synthesis.: 1.: Adhesive polymers from copper-catalyzed azide-alkyne cycloaddition [J].

Díaz, DD ;

Punna, S ;

Holzer, P ;

Mcpherson, AK ;

Sharpless, KB ;

Fokin, VV ;

Finn, MG .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2004, 42 (17) :4392-4403

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