Copper(I)-Catalyzed Coupling Cyclization of Methyl Perfluoroalk-2-ynoates with 2-Aminobenzonitriles: Synthesis of 2-Perfluoroalkylated Quinolines

被引：29

作者：

Han, Jing ^{[1
]}

Cao, Long ^{[1
]}

Bian, Linglin ^{[1
]}

Chen, Jie ^{[1
]}

Deng, Hongmei ^{[4
]}

Shao, Min ^{[4
]}

Jin, Zhijun ^{[5
]}

Zhang, Hui ^{[1
]}

Cao, Weiguo ^{[1
,2
,3
]}

机构：

[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[4] Shanghai Univ, Instrumental Anal & Res Ctr, Shanghai 200444, Peoples R China

[5] Changzheng Hosp, Dept Gynecol, Shanghai 200003, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 07期

基金：

中国国家自然科学基金;

关键词：

copper(I) catalysis; cyclization; heterocyclic synthesis; methyl perfluoroalk-2-ynoates; 2-perfluoroalkylated quinolines; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; DERIVATIVES; CHLORIDES; 4-PERFLUOROALKYLQUINOLINES; HETEROCYCLES; REAGENTS; ALKYNES;

D O I：

10.1002/adsc.201201107

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient route to 2-perfluoroalkylated quinoline derivatives through the copper(I)-mediated couplingcyclization of 2-aminobenzonitriles with methyl perfluoroalk-2-ynoates is described. Moderate to excellent yields have been achieved under mild conditions. The reaction mechanism is also discussed.

引用

页码：1345 / 1350

页数：6

共 42 条

[1] Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes:: One-pot synthesis of fluorinated quinolines [J].

Amii, H ;

Kishikawa, Y ;

Uneyama, K .

ORGANIC LETTERS, 2001, 3 (08) :1109-1112

[2] FLUORO HETEROCYCLES WITH 5-MEMBERED RINGS [J].

BURGER, K ;

WUCHERPFENNIG, U ;

BRUNNER, E .

ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 60, 1994, 60 :1-64

[3] FLUORINATED ORGANOMETALLICS - PERFLUOROALKYL AND FUNCTIONALIZED PERFLUOROALKYL ORGANOMETALLIC REAGENTS IN ORGANIC-SYNTHESIS [J].

BURTON, DJ ;

YANG, ZY .

TETRAHEDRON, 1992, 48 (02) :189-275

[4] Elemental fluorine - Part 15. Selective direct fiuorination of quinoline derivatives [J].

Chambers, RD ;

Holling, D ;

Sandford, G ;

Batsanov, AS ;

Howard, JAK .

JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (05) :661-671

[5] Palladium catalyzed synthesis of 2-trifluoromethylquinolines through a domino Sonogashira-alkyne carbocyclization process [J].

Chen, Zixian ;

Zhu, Jiangtao ;

Xie, Haibo ;

Li, Shan ;

Wu, Yongming ;

Gong, Yuefa .

CHEMICAL COMMUNICATIONS, 2010, 46 (12) :2145-2147

[6] Synthesis of 2-CF3-tetrahydroquinoline and quinoline derivatives from CF3-N-aryl-aldimine [J].

Crousse, B ;

Bégué, JP ;

Bonnet-Delpon, D .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :5009-5013

[7] Base-Promoted Heterocyclization of Fluorinated Alkynylphosphonates with Select ortho-Aminobenzonitriles [J].

Duda, Blazej ;

Tverdomed, Sergey N. ;

Ionin, Boris I. ;

Roeschenthaler, Gerd-Volker .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (19) :3684-3690

[8] ELECTROLYTIC REACTIONS OF FLUOROORGANIC COMPOUNDS .14. REGIOSELECTIVE ANODIC METHOXYLATION OF N-(FLUOROETHYL)AMINES - PREPARATION OF HIGHLY USEFUL FLUOROALKYLATED BUILDING-BLOCKS [J].

FUCHIGAMI, T ;

ICHIKAWA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :607-615

[9] Synthesis of five-, six-, and seven-membered ring lactams by Cp*Rh complex-catalyzed oxidative N-heterocyclization of amino alcohols [J].

Fujita, K ;

Takahashi, Y ;

Owaki, M ;

Yamamoto, K ;

Yamaguchi, R .

ORGANIC LETTERS, 2004, 6 (16) :2785-2788

[10] Docking study, in vitro anticancer screening and radiosensitizing evaluation of some new fluorine-containing quinoline and pyrimidoquinoline derivatives bearing a sulfonamide moiety [J].

Ghorab, Mostafa M. ;

Ragab, Fatma A. ;

Heiba, Helmy I. ;

Arafa, Reem K. ;

El-Hossary, Ebaa M. .

MEDICINAL CHEMISTRY RESEARCH, 2011, 20 (03) :388-400

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