One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles

被引：233

作者：

Hansen, TV ^{[1
]}

Wu, P ^{[1
]}

Fokin, VV ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 19期

关键词：

D O I：

10.1021/jo050163b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional groups do not interfere with the reaction, which can be performed in aqueous solvents without protection from oxygen. Since all reagents are used in stoichiometric amounts, formation of byproducts is minimized.

引用

页码：7761 / 7764

页数：4

共 21 条

[1]

Caramella P., 1984, 1 3 DIPOLAR CYCLOADD, V1, P337

[2]

Cicchi S, 2003, PROG HET CH, V15, P261

[3] Clicking functionality onto electrode surfaces [J].

Collman, JP ;

Devaraj, NK ;

Chidsey, CED .

LANGMUIR, 2004, 20 (04) :1051-1053

[4] Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae [J].

Deiters, A ;

Cropp, TA ;

Mukherji, M ;

Chin, JW ;

Anderson, JC ;

Schultz, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11782-11783

[5]

Grunanger P., 1991, CHEM HETEROCYCL COMP, V49, P1

[6]

HASSNER A, 1989, SYNTHESIS-STUTTGART, P57

[7] Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates [J].

Himo, F ;

Lovell, T ;

Hilgraf, R ;

Rostovtsev, VV ;

Noodleman, L ;

Sharpless, KB ;

Fokin, VV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :210-216

[8]

Jager V, 2002, CHEM HETEROCYCLIC CO, P361, DOI DOI 10.1002/0471221902.CH6

[9]

Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO

[10]

2-X

← 1 2 3 →