Copper-Catalyzed Direct Amination of 1,2,3-Triazole N-Oxides by C-H Activation and C-N Coupling

被引：12

作者：

Zhu, Jiayi ^{[1
]}

Kong, Yubo ^{[1
]}

Lin, Feng ^{[1
]}

Wang, Baoshuang ^{[1
]}

Chen, Zhengwang ^{[1
]}

Liu, Liangxian ^{[1
]}

机构：

[1] Gannan Normal Univ, Key Lab Organopharmaceut Chem Jiangxi Prov, Ganzhou 341000, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 07期

基金：

中国国家自然科学基金;

关键词：

Nitrogen heterocycles; C-H activation; Copper; Amination; DIRECT ARYLATION; FUNCTIONALIZATION; BENZOXAZOLES; REACTIVITY; AZOLES; BONDS; BROMIDES; AMINES;

D O I：

10.1002/ejoc.201403583

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient approach for the synthesis of 4-amino-2-aryl-1,2,3-triazole derivatives has been developed through the copper-catalyzed direct C-H amination of 2-aryl-1,2,3-triazole N-oxides under mild reaction conditions. Various amines, including primary and secondary aliphatic and aromatic amines, can be employed as effective coupling partners. The general performance of our method was also demonstrated by the oxidative amination of thiazole and imidazole N-oxides.

引用

页码：1507 / 1515

页数：9

共 66 条

[1] Direct arylations of electron-deficient (hetero)arenes with aryl or alkenyl tosylates and mesylates [J].

Ackermann, Lutz ;

Fenner, Sabine .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :430-432

[2]

[Anonymous], CURR BIOACTIVE COMP

[3]

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

[4] 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

[5] Synthesis and oxidative cyclization of 2-arylhydrazono-2-cyanoacetamidines to 5-amino-2-aryl-2H-[1,2,3]triazole-4-carbonitrile [J].

Bel'skaya, Natalia P. ;

Demina, Marina A. ;

Sapognikova, Svetlana G. ;

Fan, Zhi-Jin ;

Zhang, Hai-Ke ;

Dehaen, Wim ;

Bakulev, Vasiliy A. .

ARKIVOC, 2008, :9-21

[6] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[7] C2, C5, and C4 azole N-oxide direct arylation including room-temperature reactions [J].

Campeau, Louis-Charles ;

Bertrand-Laperle, Megan ;

Leclerc, Jean-Philippe ;

Villemure, Elisia ;

Gorelsky, Serge ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3276-+

[8] Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis [J].

Campeau, Louis-Charles ;

Stuart, David R. ;

Leclerc, Jean-Philippe ;

Bertrand-Laperle, Megan ;

Villemure, Elisia ;

Sun, Ho-Yan ;

Lasserre, Sandrine ;

Guimond, Nicolas ;

Lecavallier, Melanie ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3291-3306

[9] New N- and O-arylations with phenylboronic acids and cupric acetate [J].

Chan, DMT ;

Monaco, KL ;

Wang, RP ;

Winters, MP .

TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936

[10] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

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