Study of copper(I) catalysts for the synthesis of carbanucleosides via azide-alkyne 1,3-dipolar cycloaddition

被引：70

作者：

Broggi, Julie ^{[1
]}

Diez-Gonzalez, Silvia ^{[2
]}

Petersen, Jeffrey L. ^{[3
]}

Berteina-Raboin, Sabine ^{[1
]}

Nolan, Steven P. ^{[2
]}

Agrofoglio, Luigi A. ^{[1
]}

机构：

[1] Univ Orleans, Inst Chim Minerale & Analyt, UMR 6005, F-45067 Orleans, France

[2] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

[3] W Virginia Univ, C Eugene Bennet Dept Chem, Morgantown, WV 26506 USA

来源：

SYNTHESIS-STUTTGART | 2008年 / 01期

关键词：

copper(I) catalysts; Huisgen 1,3-dipolar cycloaddition; carbanucleosides; N-heterocyclic carbenes;

D O I：

10.1055/s-2007-990943

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The activity of three copper(I)-based catalytic systems in the preparation of various 1,2,3 -triazolyl-carbanucleosides via the Huisgen azide-alkyne 1,3-dipolar cycloaddition is presented. The influence of the alkyne substituent, solvent, and heating mode were studied. The preparation of [1,2-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]bromocopper [(IMes)CuBr] is discussed.

引用

页码：141 / 148

页数：8

共 64 条

[61] A chemoselective reduction of alkynes to (E)-alkenes [J].

Trost, BM ;

Ball, ZT ;

Jöge, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7922-7923

[62] Regiospecific synthesis and anti-human immunodeficiency virus activity of novel 5-substituted N-alkylcarbamoyl and N,N-dialkyl carbamoyl 1,2,3-triazole-TSAO analogues [J].

Velázquez, S ;

Alvarez, R ;

Pérez, C ;

Gago, F ;

De Clercq, E ;

Balzarini, J ;

Camarasa, MJ .

ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 1998, 9 (06) :481-489

[63] Advances in 1,3-dipolar cycloaddition reaction of azides and alkynes - A prototype of "click" chemistry [J].

Wang, Q ;

Chittaboina, S ;

Barnhill, HN .

LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (04) :293-301

[64] Synthesis of novel deoxy λ5 phospha sugar nucleosides:: 1,3-dipolar cycloaddition of an azidophospholane with alkynes [J].

Yamashita, M ;

Reddy, PM ;

Kato, Y ;

Reddy, VK ;

Suzuki, K ;

Oshikawa, T .

CARBOHYDRATE RESEARCH, 2001, 336 (04) :257-270

← 1 2 3 4 5 6 7 →