Synthesis of pyrido[2′,1′:2,3]imidazo[4,5-b]quinoline and pyrido[1′,2′:1,2]imidazo[4,5-b]quinoline and their benzo and aza analogs via tandem catalysis
作者： Kristof T.J. Loones , Bert U.W. Maes , Roger A. Dommisse
DOI: 10.1016/J.TET.2007.06.011
关键词:
摘要: Abstract In this paper we report regioselective tandem metal-catalyzed aminations on dihaloquinolines (2-chloro-3-iodoquinoline and 2,3-dibromoquinoline) with amino(benzo)(di)azines. Eight new heterocyclic scaffolds of the dipyridoimidazole type could be synthesized. By controlling reaction temperature selective C-2 intermolecular Pd-catalyzed amination 2,3-dibromoquinoline amino(benzo)(di)azines can achieved.
elsevier.com
core.ac.uk 
sci-hub.se 参考文章(26)
Adam F. Littke, Gregory C. Fu, Palladium-Catalyzed Coupling Reactions of Aryl Chlorides Angewandte Chemie International Edition. ,vol. 41, pp. 4176- 4211 ,(2002) , 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
Guy Koeckelberghs, Lieven De Cremer, Wouter Vanormelingen, Wim Dehaen, Thierry Verbiest, André Persoons, Celest Samyn, Improved synthesis of N-alkyl substituted dithieno[3,2-b:2′,3′-d]pyrroles Tetrahedron. ,vol. 61, pp. 687- 691 ,(2005) , 10.1016/J.TET.2004.10.106
Janis Louie, John F. Hartwig, Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents Tetrahedron Letters. ,vol. 36, pp. 3609- 3612 ,(1995) , 10.1016/0040-4039(95)00605-C
R. A. Abramovitch, D. H. Hey, The condensation of 2,3-dihydro-2-oxoimidazo[1,2-a]pyridine with o-nitrobenzaldehyde Journal of The Chemical Society C: Organic. pp. 1095- 1095 ,(1966) , 10.1039/J39660001095
Vittorio Dal Piaz, Maria P. Giovannoni, Giovanna Ciciani, Donatella Giomi, Rodolfo Nesi, Diels-alder reactions on 5-acetyl-2-methyl-4-nitro-6-phenylpyridazin-3(2H)-one: A new facet of the pyridazine system Tetrahedron Letters. ,vol. 34, pp. 161- 162 ,(1993) , 10.1016/S0040-4039(00)60083-7
Mark R. Sabol, John M. Owen, W. Randal Erickson, A Novel and Efficient Synthesis of 2,3-Dichloroquinoline Synthetic Communications. ,vol. 30, pp. 427- 432 ,(2000) , 10.1080/00397910008087338
Anil S. Guram, Roger A. Rennels, Stephen L. Buchwald, A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines Angewandte Chemie. ,vol. 34, pp. 1348- 1350 ,(1995) , 10.1002/ANIE.199513481
Kristof T. J. Loones, Bert U. W. Maes, Caroline Meyers, Joke Deruytter, Orthogonal and auto-tandem catalysis : Synthesis of dipyrido[1,2-a:2',3'-d]imidazole and its benzo and aza analogues via inter- and intramolecular C-N bond formation Journal of Organic Chemistry. ,vol. 71, pp. 260- 264 ,(2006) , 10.1021/JO052091U
Jean-Claude Teulade, Nicolas Desbois, Jean-Michel Chezal, Florence Fauvelle, Jean-Claude Debouzy, Claire Lartigue, Alain Gueiffier, Yves Blache, Emmanuel Moreau, Jean-Claude Madelmont, Olivier Chavignon, Synthesis of Polyfused Heterocycle Derivatives Containing the Dipyridoimidazole Core by Friedländer’s Reaction: Access to Analogs of Ellipticine HETEROCYCLES. ,vol. 65, pp. 1121- 1137 ,(2005) , 10.3987/COM-05-10354
F. Marsais, A. Godard, G. Queguiner, Directed ortho-lithiation of chloroquinolines. Application to synthesis of 2,3-disubstituted quinolines Journal of Heterocyclic Chemistry. ,vol. 26, pp. 1589- 1594 ,(2009) , 10.1002/JHET.5570260615