Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages

被引：375

作者：

Barral, Karine ^{[1
]}

Moorhouse, Adam D. ^{[1
]}

Moses, John E. ^{[1
]}

机构：

[1] Univ London, Sch Pharm, Dept Pharmaceut & Biol Chem, London WC1N 1AX, England

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 09期

关键词：

D O I：

10.1021/ol070527h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and improved procedure for the preparation of aromatic azides and their application in the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition ("click reaction") is described. The synthesis of aromatic azides from the corresponding amines is accomplished under mild conditions with tert-butyl nitrite and azidotrimethylsilane. 1,4-Disubstituted 1,2,3-triazoles were obtained in excellent yields from a variety of aromatic amines without the need for isolation of the azide intermediates.

引用

页码：1809 / 1811

页数：3

共 45 条

[1] Metal catalyzed diazo transfer for the synthesis of azides from amines [J].

Alper, PB ;

Hung, SC ;

Wong, CH .

TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032

[2] A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].

Appukkuttan, P ;

Dehaen, W ;

Fokin, VV ;

Van der Eycken, E .

ORGANIC LETTERS, 2004, 6 (23) :4223-4225

[3]

BAYLEY H, 1984, AZIDES NITRENES REAC, P433

[4] One-pot procedure for diazo transfer and azide-alkyne cycloaddition: Triazole linkages from amines [J].

Beckmann, Henning S. G. ;

Wittmann, Valentin .

ORGANIC LETTERS, 2007, 9 (01) :1-4

[5]

Biffin M. E. C., 1971, CHEM AZIDO GROUP, P147

[6] 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

[7] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

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

Breinbauer, R ;

Köhn, M .

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

[9] 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

[10] TRIFLUOROMETHANESULFONYL AZIDE - ITS REACTION WITH ALKYL AMINES TO FORM ALKYL AZIDES [J].

CAVENDER, CJ ;

SHINER, VJ .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) :3567-&

← 1 2 3 4 5 →