A facile synthesis of 5-amino-[1,2,3]triazolo[5,1-a]isoquinoline derivatives through copper-catalyzed cascade reactions

被引：26

作者：

Chen, Yunfeng ^{[1
]}

Zhou, Shilei ^{[1
]}

Ma, Shan ^{[1
]}

Liu, Wenqian ^{[1
]}

Pan, Zhiquan ^{[1
]}

Shi, Xiaodong ^{[2
]}

机构：

[1] Wuhan Inst Technol, Key Lab Green Chem Proc, Minist Educ, Wuhan 430073, Peoples R China

[2] W Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 47期

基金：

中国国家自然科学基金; 美国国家科学基金会;

关键词：

DIRECT ARYLATIONS; ONE-POT; TANDEM SYNTHESIS; C-C; TRANSANNULATION; BOND; 1,2,3-TRIAZOLES; TRIAZOLOPYRIDINES; ANNULATION; REACTIVITY;

D O I：

10.1039/c3ob41774c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed cascade method was developed for the synthesis of [1,2,3]triazolo[5,1-a]isoquinoline derivatives. The N-fused heterocycles were obtained in good to excellent yields under mild conditions, which provided a new strategy for the preparation of this highly functionalized building block.

引用

页码：8171 / 8174

页数：4

共 64 条

[1] 3-(2-Pyridyl)-[1,2,3]triazolo[1,5-a]pyridines.: An experimental and theoretical (DFT) study of the ring-chain isomerization [J].

Abarca, B ;

Alkorta, I ;

Ballesteros, R ;

Blanco, F ;

Chadlaoui, M ;

Elguero, J ;

Mojarrad, F .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (21) :3905-3910

[2] Triazolopyridines. Part 26: The preparation of novel [1,2,3]triazolo[1,5-a]pyridine sulfoxides [J].

Abarca, Belen ;

Ballesteros, Rafael ;

Ballesteros-Garrido, Rafael ;

Colobert, Francoise ;

Leroux, Frederic R. .

TETRAHEDRON, 2008, 64 (17) :3794-3801

[3] Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Althammer, Andreas .

ORGANIC LETTERS, 2008, 10 (11) :2299-2302

[4] Palladium-catalyzed direct arylations of 1,2,3-triazoles with aryl chlorides using conventional heating [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Born, Robert .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) :741-748

[5] Mechanistic Insight into Direct Arylations with Ruthenium(II) Carboxylate Catalysts [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Potukuchi, Harish K. ;

Pirovano, Valentina .

ORGANIC LETTERS, 2010, 12 (21) :5032-5035

[6] Regioselective syntheses of fully-substituted 1,2,3-triazoles: the CuAAC/C-H bond functionalization nexus [J].

Ackermann, Lutz ;

Potukuchi, Harish Kumar .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4503-4513

[7] Ruthenium-Catalyzed C-H Bond Functionalizations of 1,2,3-Triazol-4-yl-Substituted Arenes: Dehydrogenative Couplings Versus Direct Arylations [J].

Ackermann, Lutz ;

Novak, Petr ;

Vicente, Ruben ;

Pirovano, Valentina ;

Potukuchi, Harish K. .

SYNTHESIS-STUTTGART, 2010, (13) :2245-2253

[8] Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles [J].

Ackermann, Lutz ;

Jeyachandran, Rajkumar ;

Potukuchi, Harish K. ;

Novak, Petr ;

Buettner, Lea .

ORGANIC LETTERS, 2010, 12 (09) :2056-2059

[9] Ruthenium-Catalyzed Direct Arylations of N-Aryl 1,2,3-Triazoles with Aryl Chlorides as Electrophiles [J].

Ackermann, Lutz ;

Born, Robert ;

Vicente, Ruben .

CHEMSUSCHEM, 2009, 2 (06) :546-549

[10] Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].

Agalave, Sandip G. ;

Maujan, Suleman R. ;

Pore, Vandana S. .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718

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