Tandem epoxide or aziridine ring opening by azide/copper catalyzed [3+2] cycloaddition:: Efficient synthesis of 1,2,3-triazolo β-hydroxy or β-tosylamino functionality motif

被引：83

作者：

Kumaraswamy, Gullapalli ^{[1
]}

Ankamma, Kukkadapu ^{[1
]}

Pitchaiah, Arigala ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem 3, Fine Chem Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 25期

关键词：

D O I：

10.1021/jo701724f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[Graphics] A novel and practical procedure for the synthesis of small molecules possessing beta-hydroxy or N-tosylamino 1,2,3-triazole motif by azidation of epoxides or N-tosylaziridines with sodium azide followed by "click reaction" using eco-friendly PEG-400 as a reaction medium in the presence of 5 mol % of CuI is described. Enantiomerically pure epoxide and N-tosylaziridines were afforded in high yield with excellent ee values maintaining complete stereospecificity.

引用

页码：9822 / 9825

页数：4

共 28 条

[1] Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages [J].

Barral, Karine ;

Moorhouse, Adam D. ;

Moses, John E. .

ORGANIC LETTERS, 2007, 9 (09) :1809-1811

[2] 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

[3] 1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors [J].

Brik, A ;

Alexandratos, J ;

Lin, YC ;

Elder, JH ;

Olson, AJ ;

Wlodawer, A ;

Goodsell, DS ;

Wong, CH .

CHEMBIOCHEM, 2005, 6 (07) :1167-+

[4] One-pot synthesis of triazole-linked glycoconjugates [J].

Chittaboina, S ;

Xie, F ;

Wang, Q .

TETRAHEDRON LETTERS, 2005, 46 (13) :2331-2336

[5] Catalyst-free highly regio- and stereoselective ring opening of epoxides and aziridines with sodium azide using poly(ethylene glycol) as an efficient reaction medium [J].

Das, Biswanath ;

Reddy, Vtukuri Saidi ;

Tehseen, Fouzia ;

Krishnaiah, Maddeboina .

SYNTHESIS-STUTTGART, 2007, (05) :666-668

[6]

Huisgen R., 1963, ANGEW CHEM INT EDIT, V2, P633, DOI [10.1002/anie.196306331, DOI 10.1002/ANIE.19630633, DOI 10.1002/ANIE.196306331]

[7]

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

[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 →