Structure and properties of neutral and cationic gold(III) complexes from substituted 2-(2'-pyridyl)quinoline ligands.

A one-step catalytic synthesis of 6-substituted 4-phenyl-2-(2'-pyridyl)quinolines provides electronically differentiated ligands without solvent, inert atmosphere, metal contamination, or chromatography. Gold(III) complexes formed from these bidentate PyQuin ligands were characterized and studied by single-crystal X-ray diffraction. The cationic gold(III) chloride synthesized from 6-methoxy-4-phenyl-2-(2'-pyridyl)quinoline has a distorted square-planar ligand environment. Diamagnetic neutral gold(III) complexes from methoxy-, methyl-, and phenyl-PyQuin ligands exhibit a long axial Au-N2 interaction.

[1]  Catharine H. Larsen,et al.  One-step catalytic synthesis of alkyl-substituted quinolines. , 2014, The Journal of organic chemistry.

[2]  U. Dzhemilev,et al.  Metal Complex Catalysis in the Synthesis of Quinolines , 2014 .

[3]  Jack F. Eichler,et al.  Antitumor properties of five-coordinate gold(III) complexes bearing substituted polypyridyl ligands. , 2013, Journal of inorganic biochemistry.

[4]  S. Galli,et al.  Rollover cyclometalation with 2-(2'-pyridyl)quinoline. , 2013, Inorganic chemistry.

[5]  K. Papadopoulos,et al.  Novel Ru(II) sensitizers bearing an unsymmetrical pyridine-quinoline hybrid ligand with extended π-conjugation: synthesis and application in dye-sensitized solar cells. , 2013, Dalton transactions.

[6]  A. Philippopoulos,et al.  Synthesis, biochemical evaluation and molecular modeling studies of novel rhodium complexes with nanomolar activity against Platelet Activating Factor. , 2013, Journal of inorganic biochemistry.

[7]  Jeffrey P. Jones,et al.  Comparative study of the affinity and metabolism of type I and type II binding quinoline carboxamide analogues by cytochrome P450 3A4. , 2012, Journal of medicinal chemistry.

[8]  R. Thummel,et al.  Polydentate analogues of 8-hydroxyquinoline and their complexes with ruthenium. , 2011, Inorganic chemistry.

[9]  C. Che,et al.  Therapeutic applications of gold complexes: lipophilic gold(III) cations and gold(I) complexes for anti-cancer treatment. , 2011, Chemical communications.

[10]  M. Sigman,et al.  On the mechanism of the palladium-catalyzed tert-butylhydroperoxide-mediated Wacker-type oxidation of alkenes using quinoline-2-oxazoline ligands. , 2011, Journal of the American Chemical Society.

[11]  Jack F. Eichler,et al.  Tumor cytotoxicity of 5,6-dimethyl-1,10-phenanthroline and its corresponding gold(III) complex. , 2011, Journal of inorganic biochemistry.

[12]  K. C. Majumdar,et al.  Efficient One-Pot Synthesisof Substituted 4,7-Phenanthroline, Pyrano-[3,2-f]quinoline and Pyrano[3,2-g]quinoline Derivatives by Aza-Diels-Alder Reaction , 2011 .

[13]  A. Casini,et al.  [Au2(phen(2Me))2(μ-O)2](PF6)2, a Novel Dinuclear Gold(III) Complex Showing Excellent Antiproliferative Properties. , 2010, ACS medicinal chemistry letters.

[14]  A. Casini,et al.  Synthesis, characterisation and biological properties of gold(III) compounds with modified bipyridine and bipyridylamine ligands. , 2010, Dalton transactions.

[15]  Jack F. Eichler,et al.  Synthesis and characterization of gold(III) complexes possessing 2,9-dialkylphenanthroline ligands: to bind or not to bind? , 2009, Dalton transactions.

[16]  I. Ott.  On the medicinal chemistry of gold complexes as anticancer drugs , 2009 .

[17]  Chao-Jun Li,et al.  Green chemistry for chemical synthesis , 2008, Proceedings of the National Academy of Sciences.

[18]  F Dean Toste,et al.  Ligand effects in homogeneous Au catalysis. , 2008, Chemical reviews.

[19]  A. Arcadi.  Alternative synthetic methods through new developments in catalysis by gold. , 2008, Chemical reviews.

[20]  Roger A Sheldon,et al.  E factors, green chemistry and catalysis: an odyssey. , 2008, Chemical communications.

[21]  Zigang Li,et al.  Gold-catalyzed organic transformations. , 2008, Chemical reviews.

[22]  A Stephen K Hashmi,et al.  Gold-catalyzed organic reactions. , 2007, Chemical reviews.

[23]  Ryoji Noyori,et al.  Pursuing practical elegance in chemical synthesis. , 2005, Chemical communications.

[24]  N. Krause,et al.  The golden gate to catalysis. , 2005, Organic & biomolecular chemistry.

[25]  C. Shaw.  Gold-Based Therapeutic Agents , 1999 .

[26]  M. Sadiq,et al.  Mutagenic activity of rhodium(III) complexes with 2,2′-biquinoline and 2-(2′-pyridyl)quinoline , 1997 .

[27]  S. Campagna,et al.  Synthesis, characterization, luminescence properties, and electrochemical behaviour of ruthenium(II) complexes with two new bi- and tri-dentate 2-pyridylquinoline ligands , 1991 .

[28]  C. O'connor,et al.  Synthesis, structure, and properties of trichloro- and tribromo(2-(2'-pyridyl)quinoline)gold(III) , 1978 .

[29]  W. Robinson,et al.  Synthesis, structure, and properties of trichloro- and tribromo-(2,9-dimethyl-1,10-phenanthroline)gold(III) , 1975 .

[30]  S. Kokot,et al.  High- and low-spin complexes with similar, ligands: II. Iron(II) complexes with sterically hindered analogues of 2, 2'-bipyridyl , 1972 .

[31]  C. Harris,et al.  Five-coordinate gold(III) complexes of 2,2′-biquinolyl , 1966 .

[32]  A. P. Smirnoff.  Über gepaarte Cyclamine I: 2‐(2‐Chinolyl)‐cyclamine; Valenzformel des Chinolins , 1921 .