Cu(II)-promoted three-component coupling sequence for the efficient synthesis of substituted quinolines.

The copper-promoted three-component coupling sequence for substituted quinoline formation from aldehydes, anilines and acetone is described. Various 2-arylquinolines were selectively obtained in good yields under mild conditions. The reaction tolerated a wide range of functionalities.

[1]  Huanfeng Jiang,et al.  Palladium-catalyzed sequential formation of C-C bonds: efficient assembly of 2-substituted and 2,3-disubstituted quinolines. , 2012, Angewandte Chemie.

[2]  Chao‐Jun Li,et al.  Iron-catalyzed arylation of benzoazoles with aromatic aldehydes using oxygen as oxidant , 2012 .

[3]  Yong‐Gui Zhou,et al.  Dihydrophenanthridine: a new and easily regenerable NAD(P)H model for biomimetic asymmetric hydrogenation. , 2012, Journal of the American Chemical Society.

[4]  A. Edmunds,et al.  Ligand-promoted C3-selective arylation of pyridines with Pd catalysts: gram-scale synthesis of (±)-preclamol. , 2011, Journal of the American Chemical Society.

[5]  Scott J. Miller,et al.  Iridium-catalyzed hydrogenation of N-heterocyclic compounds under mild conditions by an outer-sphere pathway. , 2011, Journal of the American Chemical Society.

[6]  Yongping Liang,et al.  Electrophile-driven regioselective synthesis of functionalized quinolines. , 2011, Organic letters.

[7]  Chao‐Jun Li,et al.  Palladium-catalyzed oxidative sp2 C-H bond acylation with alcohols. , 2011, Organic letters.

[8]  R. Madsen,et al.  Ruthenium-catalysed synthesis of 2- and 3-substituted quinolines from anilines and 1,3-diols. , 2011, Organic & biomolecular chemistry.

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

[10]  Preston A. Chase,et al.  Metal-free reductions of N-heterocycles via Lewis acid catalyzed hydrogenation. , 2010, Chemical communications.

[11]  V. Venditto,et al.  Cancer therapies utilizing the camptothecins: a review of the in vivo literature. , 2010, Molecular pharmaceutics.

[12]  Arpan K. Shah,et al.  Direct Mannich reaction mediated by Fe(Cp)2PF6 under solvent-free conditions , 2010 .

[13]  A. Kapdi,et al.  Transition-metal-catalyzed direct arylation of (hetero)arenes by C-H bond cleavage. , 2009, Angewandte Chemie.

[14]  C. K. Venil,et al.  Benzimidazole quinoline derivatives — An effective green fluorescent dye for bacterial imaging , 2009 .

[15]  N. Chatani,et al.  Nickel-catalyzed reaction of arylzinc reagents with N-aromatic heterocycles: a straightforward approach to C-H bond arylation of electron-deficient heteroaromatic compounds. , 2009, Journal of the American Chemical Society.

[16]  Xiao‐Qi Yu,et al.  Lipase-catalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for C―C bond formation in a one-pot synthesis , 2009 .

[17]  E. Gondek,et al.  Photoluminescence of 1,3-dimethyl pyrazoloquinoline derivatives , 2009 .

[18]  Abdelouahid Samadi,et al.  Recent advances in the Friedländer reaction. , 2009, Chemical reviews.

[19]  Annamaria Lilienkampf,et al.  Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis. , 2009, Journal of medicinal chemistry.

[20]  Z. Tan,et al.  Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat-TAR interaction inhibitors. , 2009, Bioorganic & medicinal chemistry.

[21]  J. Ellman,et al.  Rh(I)-catalyzed direct arylation of pyridines and quinolines. , 2008, Journal of the American Chemical Society.

[22]  S. Buchwald,et al.  Sequential Cu-catalyzed amidation-base-mediated camps cyclization: a two-step synthesis of 2-Aryl-4-quinolones from o-halophenones. , 2007, The Journal of organic chemistry.

[23]  P. Plastina,et al.  Novel and convenient synthesis of substituted quinolines by copper- or palladium-catalyzed cyclodehydration of 1-(2-aminoaryl)-2-yn-1-ols. , 2007, The Journal of organic chemistry.

[24]  P. DeShong,et al.  Reductive cyclization of o-nitrophenyl propargyl alcohols: facile synthesis of substituted quinolines. , 2007, Organic letters.

[25]  P. Ding,et al.  Synthesis of substituted 1,2-dihydroquinolines and quinolines from aromatic amines and alkynes by gold(I)-catalyzed tandem hydroamination-hydroarylation under microwave-assisted conditions. , 2007, Organic letters.

[26]  Meghana S. Rasalkar,et al.  Heteropoly acid in ionic liquid — An efficient and recyclable system for one-pot three-component Mannich reaction , 2007 .

[27]  V. Litvinov.  Advances in the Chemistry of Naphthyridines , 2006 .

[28]  J. S. Carey,et al.  Analysis of the reactions used for the preparation of drug candidate molecules. , 2006, Organic & biomolecular chemistry.

[29]  S. Yamashkin,et al.  Traditional and modern approaches to the synthesis of quinoline systems by the Skraup and Doebner-Miller methods. (Review) , 2006 .

[30]  Carlos M. Meléndez Gómez,et al.  Recent Progress in the Synthesis of Quinolines , 2005 .

[31]  K. Godula,et al.  Site-specific phenylation of pyridine catalyzed by phosphido-bridged ruthenium dimer complexes: a prototype for C-H arylation of electron-deficient heteroarenes. , 2005, Journal of the American Chemical Society.

[32]  C. Cho,et al.  Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: modified Friedlaender quinoline synthesis , 2001 .

[33]  J. Collin,et al.  Imino-Diels–Alder and imino-aldol reactions catalyzed by samarium diiodide , 2001 .

[34]  C. Tzeng,et al.  Synthesis and antibacterial evaluation of certain quinolone derivatives. , 2001, Journal of medicinal chemistry.

[35]  Wakatsuki,et al.  Ruthenium-Catalyzed Intermolecular Hydroamination of Terminal Alkynes with Anilines: A Practical Synthesis of Aromatic Ketimines. , 1999, Angewandte Chemie.

[36]  G. Zanardi,et al.  DDQ-mediated formation of carboncarbon bonds: Oxidation of imines , 1993 .

[37]  F. Ruggieri,et al.  Annulation reactions with iron(III) chloride: oxidation of imines , 1992 .

[38]  E. W. Cohn.  A MODIFICATION OF THE SKRAUP SYNTHESIS OF QUINOLINE , 1928 .