Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes

被引：146

作者：

Cano, Israel ^{[2
]}

Alvares, Eleuterio ^{[3
]}

Carmen Nicasio, M. ^{[1
]}

Perez, Pedro J. ^{[2
]}

机构：

[1] Univ Seville, Dept Quim Inorgan, Seville 41071, Spain

[2] Univ Huelva, Ctr Invest Quim Sostenible CIQSO, Unidad Asociada CSIC, Dept Quim & Ciencias Mat,Lab Catalisis Homogenea, Huelva 21007, Spain

[3] Univ Seville, CSIC, Inst Invest Quim, Seville 41092, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 02期

关键词：

ONE-POT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITIONS; EFFICIENT SYNTHESIS; DIRECT ALKYNYLATION; CATALYZED SYNTHESIS; SOLID-PHASE; COPPER; ALKYNE; ALCOHOLS; CYCLOISOMERIZATION;

D O I：

10.1021/ja109732s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of 1-alkynes with acyl azides in the presence of [Tpm*Cu-,Cu-Br(NCMe)]BF4 [Tpm*(,Br) = tris(3,5-dimethyl-4-bromopyrazolyl)methane] as the catalyst provides 2,5-oxazoles in moderate to high yields. This is a novel transformation of the CuAAC type that constitutes a significant variation of the commonly observed [3 + 2] cycloaddition reaction to yield 1,2,3-triazoles.

引用

页码：191 / 193

页数：3

共 58 条

[1] Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine [J].

Bae, I ;

Han, H ;

Chang, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2038-2039

[2] Synthesis of functionalised oxazoles and bis-oxazoles [J].

Bagley, MC ;

Buck, RT ;

Hind, SL ;

Moody, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03) :591-600

[3] Tandem C-C coupling - intramolecular acetylenic Schmidt reaction under Pd/C-Cu catalysis [J].

Batchu, Venkateswara Rao ;

Barange, Deepak Kumar ;

Kumar, Dinesh ;

Sreekanth, Bukkapattanam R. ;

Vyas, K. ;

Reddy, E. Amarender ;

Pal, Manojit .

CHEMICAL COMMUNICATIONS, 2007, (19) :1966-1968

[4] Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes [J].

Besselievre, Francois ;

Piguel, Sandrine ;

Mahuteau-Betzer, Florence ;

Grierson, David S. .

ORGANIC LETTERS, 2008, 10 (18) :4029-4032

[5] Copper as a Powerful Catalyst in the Direct Alkynylation of Azoles [J].

Besselievre, Francois ;

Piguel, Sandrine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9553-9556

[6] Metal catalyzed multicomponent syntheses of secondary propargylamides and oxazoles from silylimines, acid chlorides, and alkynes [J].

Black, DA ;

Arndtsen, BA .

TETRAHEDRON, 2005, 61 (48) :11317-11321

[7] 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

[8] Modulating the reactivity of α-isocyanoacetates:: Multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones [J].

Bonne, Damien ;

Dekhane, Mouloud ;

Zhu, Jieping .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2485-2488

[9] Copper(I) complexes as catalysts for the synthesis of N-sulfonyl-1,2,3-triazoles from N-sulfonylazides and alkynes [J].

Cano, Israel ;

Nicasio, M. Carmen ;

Perez, Pedro J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (03) :536-538

[10] Catalytic one-pot synthesis of cyclic amidines by virtue of tandem reactions involving intramolecular hydroamination under mild conditions [J].

Chang, Sukbok ;

Lee, Minjae ;

Jung, Doo Young ;

Yoo, Eun Jeong ;

Cho, Seung Hwan ;

Han, Sun Kyu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (38) :12366-12367

← 1 2 3 4 5 6 →