Microwave enhancement of a 'one-pot' tandem azidation-'click' cycloaddition of anilines

被引：57

作者：

Moorhouse, Adam D. ^{[1
]}

Moses, John. E. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

SYNLETT | 2008年 / 14期

基金：

英国工程与自然科学研究理事会;

关键词：

click chemistry; aromatic azides; Huisgen cycloaddition; chemoselectivity; 1,4-triazoles;

D O I：

10.1055/s-2008-1078019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The practical and efficient one-pot azidation of anilines with the reagent combination t-BuONO and TMSN3 has become a useful addition to the click-chemistry toolbox. Herein we report a modification of this methodology, using microwave radiation to significantly enhance the rate of fori-nation of 1,4-triazoles from in situ generated azides.

引用

页码：2089 / 2092

页数：4

共 20 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] 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

[3] Azide/alkyne-"click" reactions: Applications in material science and organic synthesis [J].

Binder, Wolfgang H. ;

Kluger, Christian .

CURRENT ORGANIC CHEMISTRY, 2006, 10 (14) :1791-1815

[4] 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

[5] Three-component coupling of alkynes, Baylis-Hillman adducts and sodium azide: a new synthesis of substituted triazoles [J].

Chandrasekhar, S ;

Basu, D ;

Rambabu, C .

TETRAHEDRON LETTERS, 2006, 47 (18) :3059-3063

[6] Triazole: the keystone in glycosylated molecular architectures constructed by a click reaction [J].

Dondoni, Alessandro .

CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (06) :700-708

[7] One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides [J].

Feldman, AK ;

Colasson, B ;

Fokin, VV .

ORGANIC LETTERS, 2004, 6 (22) :3897-3899

[8] Copper(II) triflate as a double catalyst for the one-pot click synthesis of 1,4-disubstituted 1,2,3-triazoles from benzylic acetates [J].

Fukuzawa, Shin-ichi ;

Shimizu, Eiji ;

Kikuchi, Satoshi .

SYNLETT, 2007, (15) :2436-2438

[9] Bringing efficiency to materials synthesis: The philosophy of click chemistry [J].

Hawker, Craig J. ;

Fokin, Valery V. ;

Finn, M. G. ;

Sharpless, K. Barry .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2007, 60 (06) :381-383

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

Kolb, HC ;

Sharpless, KB .

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

← 1 2 →