Efficient synthesis of 2-substituted-1,2,3-triazoles

被引：176

作者：

Kalisiak, Jaroslaw

Sharpless, K. Barry

Fokin, Vallery V.

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 15期

关键词：

D O I：

10.1021/ol8006748

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this three-component reaction, alkynes undergo a copper(I)-catalyzed cycloaddition with sodium azide and formaldehyde to yield 2-hydroxymethyl-2H-1,2,3-triazoles, which are useful intermediates that can be readily converted to polyfunctional molecules. The hydroxymethyl group can also be removed, providing convenient access to NH-1,2,3-triazoles. The reaction is experimentally simple and readily scalable.

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页码：3171 / 3174

页数：4

相关论文

共 28 条

[1]

Alkorta I, 2004, J HETEROCYCLIC CHEM, V41, P285, DOI 10.1002/jhet.5570410223

[2] Direct Pd-catalyzed arylation of 1,2,3-triazoles [J].

Chuprakov, Stepan ;

Chernyak, Natalia ;

Dudnik, Alexander S. ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2007, 9 (12) :2333-2336

[3] Anionic, in situ generation of formaldehyde: A very useful and versatile tool in synthesis [J].

Deguest, Geoffrey ;

Bischoff, Laurent ;

Fruit, Corinne ;

Marsais, Francis .

ORGANIC LETTERS, 2007, 9 (06) :1165-1167

[4] STUDIES IN THE PROTECTION OF PYRROLE AND INDOLE-DERIVATIVES [J].

DHANAK, D ;

REESE, CB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12) :2181-2186

[5] REACTIONS OF CARBINOLAMINES .3. COMPLEX METAL HYDRIDE REACTIONS .2. REDUCTION OF 1-HYDROXYMETHYL AND 1-BENZOYL-OXYMETHYL-1H-BENZOTRIAZOLE [J].

GAYLORD, NG ;

KAY, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (10) :1574-1575

[6]

Huisgen R., 1984, 1 3 DIPOLAR CYCLOADD

[7] Azoles .13. Synthesis and bromine->lithium exchange reactions of some 1-substituted 4,5-dibromo-1H-1,2,3-triazoles and 2-substituted 4,5-dibromo-2H-1,2,3-triazoles [J].

Iddon, B ;

Nicholas, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (12) :1341-1347

[8] 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

[9] Highly efficient and mild synthesis of variously 5-substituted-4-carbaldehyde-1,2,3-triazole derivatives [J].

Journet, M ;

Cai, DW ;

Kowal, JJ ;

Larsen, RD .

TETRAHEDRON LETTERS, 2001, 42 (52) :9117-9118

[10] 4-Aryl-1,2,3-triazole: A novel template for a reversible methionine aminopeptidase 2 inhibitor, optimized to inhibit angiogenesis in vivo [J].

Kallander, LS ;

Lu, Q ;

Chen, WF ;

Tomaszek, T ;

Yang, G ;

Tew, D ;

Meek, TD ;

Hofmann, GA ;

Schulz-Pritchard, CK ;

Smith, WW ;

Janson, CA ;

Ryan, MD ;

Zhang, GF ;

Johanson, KO ;

Kirkpatrick, RB ;

Ho, TF ;

Fisher, PW ;

Mattern, MR ;

Johnson, RK ;

Hansbury, MJ ;

Winkler, JD ;

Ward, KW ;

Veber, DF ;

Thompson, SK .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (18) :5644-5647