Copper-Catalyzed Cascade Synthesis of Alkyl 6-Aminobenzimidazo[2,1-a]isoquinoline-5-carboxylates

被引：35

作者：

Lu, Juyou ^{[1
]}

Fu, Hua ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 11期

基金：

中国国家自然科学基金;

关键词：

ALPHA-AMINO-ACID; C-N; BENZODIAZEPINE-RECEPTOR; EFFICIENT SYNTHESIS; COUPLING REACTIONS; ARYL HALIDES; DERIVATIVES; ARYLATION; ULLMANN; LIGAND;

D O I：

10.1021/jo200508q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and efficient copper-catalyzed cascade method has been developed for synthesis of benzimidazoisoquinoline derivatives via reactions of readily available substituted 2-(2-halophenyObenzoimidazoles with alkyl cyanoacetates under mild condition, and the corresponding alkyl 6-aminobenzimidazo[2,1-a]isoquinoline-5-carboxylates were obtained in good to excellent yields. The novel method provides diverse and useful poly N-heterocyclic compounds for combinatorial chemistry and medicinal chemistry.

引用

页码：4600 / 4605

页数：6

共 66 条

[61] A Simple Copper-Catalyzed Cascade Synthesis of 2-Amino-1H-indole-3-carboxylate Derivatives [J].

Yang, Xiaobo ;

Fu, Hua ;

Qiao, Renzhong ;

Jiang, Yuyang ;

Zhao, Yufen .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) :1033-1038

[62] Synthesis,fluorine-18 radiolabeling, and in vitro characterization of 1-iodophenyl-N-methyl-N-fluoroalkyl-3-isoquinoline carboxamide derivatives as potential PET radioligands for imaging peripheral benzodiazepine receptor [J].

Yu, Weiping ;

Wang, Eric ;

Voll, Ronald J. ;

Miller, Andrew H. ;

Goodman, Mark M. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (11) :6145-6155

[63] Copper-catalyzed double N-alkenylation of amides:: An efficient synthesis of di- or trisubstituted N-acylpyrroles [J].

Yuan, Xiyuan ;

Xu, Xiaobing ;

Zhou, Xiaobo ;

Yuan, Jiwei ;

Mai, Lugen ;

Li, Yanzhong .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1510-1513

[64] Synthesis and evaluation of a series of novel 2-[(4-chlorophenoxy)methyl]benzimidazoles as selective neuropeptide Y Y1 receptor antagonists [J].

Zarrinmayeh, H ;

Nunes, AM ;

Ornstein, PL ;

Zimmerman, DM ;

Arnold, MB ;

Schober, DA ;

Gackenheimer, SL ;

Bruns, RF ;

Hipskind, PA ;

Britton, TC ;

Cantrell, BE ;

Gehlert, DR .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (15) :2709-2719

[65] Highly efficient copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides [J].

Zhu, Liangbo ;

Cheng, Liang ;

Zhang, Yuxi ;

Xie, Rugang ;

You, Jingsong .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08) :2737-2743

[66] Synthesis of 1,2-disubstituted benzimidazoles by a Cu-catalyzed cascade aryl amination/condensation process [J].

Zou, Benli ;

Yuan, Qiliang ;

Ma, Dawei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (15) :2598-2601

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