Three component, regioselective, one-pot synthesis of β-hydroxytriazoles from epoxides via 'click reactions'

被引：76

作者：

Yadav, J. S. ^{[1
]}

Reddy, B. V. Subba ^{[1
]}

Reddy, G. Madhusudhan ^{[1
]}

Chary, D. Narasimha ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 49期

关键词：

epoxides; 2-azidoalcohols; alkynes; click reaction; triazoles;

D O I：

10.1016/j.tetlet.2007.09.160

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Azidoalcohols derived in situ from epoxides and sodium azide undergo smooth coupling with alkynes under neutral conditions by means of 'click reactions' to furnish beta-hydroxytriazoles in excellent yields and with high regioselectivity. This reaction proceeds smoothly in water at room temperature without the need for acid catalysis. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8773 / 8776

页数：4

共 26 条

[1] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

[2] Directed DNA metallization [J].

Burley, GA ;

Gierlich, J ;

Mofid, MR ;

Nir, H ;

Tal, S ;

Eichen, Y ;

Carell, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1398-1399

[3]

Fan W. Q., 1996, COMPREHENSIVE HETERO, V4, P1, DOI DOI 10.1016/B978-008096518-5.00079-4

[4] Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis [J].

Genin, MJ ;

Allwine, DA ;

Anderson, DJ ;

Barbachyn, MR ;

Emmert, DE ;

Garmon, SA ;

Graber, DR ;

Grega, KC ;

Hester, JB ;

Hutchinson, DK ;

Morris, J ;

Reischer, RJ ;

Ford, CW ;

Zurenko, GE ;

Hamel, JC ;

Schaadt, RD ;

Stapert, D ;

Yagi, BH .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) :953-970

[5] γ-Methyl-substituted-γ-butyrolactones:: solid-phase synthesis employing a cyclisation-cleavage strategy [J].

Gouault, N ;

Cupif, JF ;

Sauleau, A ;

David, M .

TETRAHEDRON LETTERS, 2000, 41 (38) :7293-7297

[6]

Huisgen R., 1963, Angew. Chem. Int. Ed, V2, P565, DOI DOI 10.1002/ANIE.196305651

[7] SYNTHESIS AND BETA-LACTAMASE INHIBITORY ACTIVITY OF 6-[(1-HETEROARYLTHIOETHYL-1,2,3-TRIAZOL-4-YL)-METHYLENE]PENAM SULFONES [J].

IM, C ;

MAITI, SN ;

MICETICH, RG ;

DANESHTALAB, M ;

ATCHISON, K ;

PHILLIPS, OA ;

KUNUGITA, C .

JOURNAL OF ANTIBIOTICS, 1994, 47 (09) :1030-1040

[8] The growing impact of click chemistry on drug discovery [J].

Kolb, HC ;

Sharpless, KB .

DRUG DISCOVERY TODAY, 2003, 8 (24) :1128-1137

[9]

Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO

[10]

2-5

← 1 2 3 →