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

An efficient route to 2-perfluoroalkylated quinoline derivatives through the copper(I)-mediated coupling–cyclization 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.

[1]  Xue‐Wei Liu,et al.  Copper(II)/iron(III) co-catalyzed intermolecular diamination of alkynes: facile synthesis of imidazopyridines. , 2012, Organic letters.

[2]  G. Röschenthaler,et al.  Base-Promoted Heterocyclization of Fluorinated Alkynylphosphonates with Select ortho-Aminobenzonitriles , 2012 .

[3]  Xue-Yuan Liu,et al.  Copper-catalyzed oxidative cyclization of enynes for the synthesis of 4-carbonyl-quinolines with O2. , 2012, Organic letters.

[4]  G. Zou,et al.  An efficient synthesis of 2-trifluoromethyl quinolines via gold-catalyzed cyclization of trifluoromethylated propargylamines , 2012 .

[5]  M. Geng,et al.  Expeditious one-pot synthesis of C3-piperazinyl-substituted quinolines: key precursors to potent c-Met inhibitors. , 2011, Organic & biomolecular chemistry.

[6]  V. Solomon,et al.  Quinoline as a privileged scaffold in cancer drug discovery. , 2011, Current medicinal chemistry.

[7]  W. Cao,et al.  First one-pot stereoselective synthesis of cis-2,3-dihydro-4-perfluoroalkyl-1H-1,5-benzodiazepines via a catalyst-free three-component reaction. , 2011, Chemical communications.

[8]  F. Ragab,et al.  Docking study, in vitro anticancer screening and radiosensitizing evaluation of some new fluorine-containing quinoline and pyrimidoquinoline derivatives bearing a sulfonamide moiety , 2011, Medicinal Chemistry Research.

[9]  Kirandeep Kaur,et al.  Quinolines and structurally related heterocycles as antimalarials. , 2010, European journal of medicinal chemistry.

[10]  Haibo Xie,et al.  Efficient Synthesis of 2‐Fluoromethylated Quinolines via Copper‐Catalyzed Alkynylation and Cyclization of Fluorinated Imidoyl Iodides , 2010 .

[11]  Haibo Xie,et al.  Palladium catalyzed synthesis of 2-trifluoromethylquinolines through a domino Sonogashira-alkyne carbocyclization process. , 2010, Chemical communications.

[12]  W. Cao,et al.  A simple and convenient synthesis of 2-(perfluoroalkyl)-4H-chromenes from salicyl N-tosylimines or salicylaldehydes and methyl 2-perfluoroalkynoates , 2009 .

[13]  M. S. Subhas,et al.  Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines. , 2009, Organic & biomolecular chemistry.

[14]  K. Uneyama,et al.  Palladium-catalyzed chloroimination of imidoyl chlorides to a triple bond: an intramolecular reaction leading to 4-chloroquinolines. , 2008, Organic letters.

[15]  K. Uneyama,et al.  One-pot synthesis of 3-fluoro-4-(trifluoromethyl)quinolines from pentafluoropropen-2-ol and their molecular modification. , 2008, The Journal of organic chemistry.

[16]  M. Mąkosza,et al.  Synthesis of trifluoromethylated azines via nucleophilic oxidative substitution of hydrogen by trifluoromethyl carbanions. , 2007, The Journal of organic chemistry.

[17]  P. Laurent,et al.  New regiospecific synthesis of 2-trifluoromethyl-1,5 diazapentadiene compounds and of 2-trifluoromethylquinolines, their cyclization products. , 2005, The Journal of organic chemistry.

[18]  B. Usachev,et al.  A simple and highly efficient synthesis of N-phenyl-2-polyfluoroalkyl-4-quinolones from 2-anilinoacetophenone and RFCO2Et , 2004 .

[19]  Ken-Ichi Fujita,et al.  Synthesis of five-, six-, and seven-membered ring lactams by CpRh complex-catalyzed oxidative N-heterocyclization of amino alcohols. , 2004, Organic letters.

[20]  J. Howard,et al.  Elemental fluorine: Part 15. Selective direct fluorination of quinoline derivatives , 2004 .

[21]  J. Charris,et al.  Synthesis of 2-trifluoromethyl-1(substituted aryl)-4(1H)-quinolones using trifluoroacetamidoyl chlorides , 2003 .

[22]  W. D. Loehle,et al.  Synthesis of fluorinated heterocycles , 2002 .

[23]  Samson A. Jenekhe,et al.  New Conjugated Polymers with Donor−Acceptor Architectures: Synthesis and Photophysics of Carbazole−Quinoline and Phenothiazine−Quinoline Copolymers and Oligomers Exhibiting Large Intramolecular Charge Transfer , 2001 .

[24]  H. Amii,et al.  Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes: one-pot synthesis of fluorinated quinolines. , 2001, Organic letters.

[25]  R. Singh,et al.  Nucleophilic Trifluoromethylation Reactions of Organic Compounds with (Trifluoromethyl)trimethylsilane , 2000 .

[26]  B. Crousse,et al.  Synthesis of 2-CF(3)-tetrahydroquinoline and quinoline derivatives from CF(3)-N-aryl-aldimine. , 2000, The Journal of organic chemistry.

[27]  L. Strekowski,,et al.  The Friedländer synthesis of 4-perfluoroalkylquinolines , 2000 .

[28]  J. Takaya,et al.  Mannich-Type Reaction with Trifluoromethylated N,O-Hemiacetal: Facile Preparation of β-Amino-β-trifluoromethyl Carbonyl Compounds , 2000 .

[29]  Scott D. Taylor,et al.  Recent advances in electrophilic fluorination , 1999 .

[30]  L. Strekowski,,et al.  Synthesis of 4-perfluoroalkylquinolines , 1998 .

[31]  M. Schlosser,et al.  How 2-anilinovinyl perfluoroalkyl ketones can be mechanistically correlated with their cyclization products 2-(perfluoroalkyl)quinolines , 1997 .

[32]  A. Yudin,et al.  Perfluoroalkylation with Organosilicon Reagents. , 1997, Chemical reviews.

[33]  S. Stanforth,et al.  The Wittig reaction of some fluorinated amide derivatives , 1994 .

[34]  T. Fuchigami,et al.  Electrolytic Reactions of Fluoroorganic Compounds. 14. Regioselective Anodic Methoxylation of N-(Fluoroethyl)amines. Preparation of Highly Useful Fluoroalkylated Building Blocks , 1994 .

[35]  Uwe Wucherpfennig,et al.  Fluoro Heterocycles with Five-Membered Rings , 1994 .

[36]  M. A. McClinton,et al.  Trifluoromethylations and related reactions in organic chemistry , 1992 .

[37]  Zhen Yang,et al.  Fluorinated Organometallics: Perfluoroalkyl and Functionalized Perfluoroalkyl Organometallic Reagents in Organic Synthesis , 1992 .

[38]  B. Hamper.  Direct synthesis of .beta.-ketomethylenetriphenylphosphoranes from readily available phosphonium salts , 1988 .