Copper-Mediated Synthesis of 1,2,3-Triazoles from N-Tosylhydrazones and Anilines

被引：156

作者：

Chen, Zhengkai ^{[1
]}

Yan, Qiangqiang ^{[1
]}

Liu, Zhanxiang ^{[1
]}

Xu, Yiming ^{[1
]}

Zhang, Yuhong ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 50期

关键词：

aniline derivatives; copper; hydrazones; synthetic methods; triazoles; HIGHLY REGIOSELECTIVE SYNTHESIS; AZIDE-ALKYNE CYCLOADDITION; EFFICIENT SYNTHESIS; 1.3-DIPOLARE CYCLOADDITIONEN; SULFONYL ALDIMINES; CATALYZED CASCADE; TERMINAL ALKYNES; ORGANIC AZIDES; BOND-FORMATION; SODIUM-AZIDE;

D O I：

10.1002/anie.201306416

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

NNNifty targets: In a straightforward copper-mediated synthesis of 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles, readily available aniline and N-tosylhydrazone substrates underwent cyclization through Cï£¿N and Nï£¿N bond formation (see scheme; Piv=pivaloyl, Ts=p-toluenesulfonyl). This method enables the preparation of 1,2,3-triazoles with high efficiency under mild conditions without the use of azides. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：13324 / 13328

页数：5

共 82 条

[1] DIPOLAR CYCLO-ADDITION REACTIONS OF ORGANIC AZIDES WITH SOME ACETYLENIC-COMPOUNDS [J].

ABUORABI, ST ;

ATFAH, MA ;

JIBRIL, I ;

MARII, FM ;

ALI, AAS .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (05) :1461-1468

[2]

[Anonymous], 2011, ANGEW CHEM

[3]

[Anonymous], 2007, ANGEW CHEM

[4]

[Anonymous], 2006, Angew. Chem, DOI DOI 10.1002/ANGE.200602917

[5]

[Anonymous], 2010, ANGEW CHEM, V122, P7957

[6]

Armstrong A., 2010, Angew. Chem, V122, P2332

[7] Direct Azole Amination: C-H Functionalization as a New Approach to Biologically Important Heterocycles [J].

Armstrong, Alan ;

Collins, James C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (13) :2282-2285

[8]

Barluenga J., 2006, ANGEW CHEM, V118, P7047, DOI DOI 10.1002/ANGE.200601045

[9]

Barluenga J., 2011, Angew. Chem, V123, P7626

[10]

Barluenga J., 2012, ANGEW CHEM, V124, P6052

← 1 2 3 4 5 6 7 8 9 →