Palladium-catalyzed N-monoarylation of amidines and a one-pot synthesis of quinazoline derivatives.
作者： Meredeth A. McGowan , Camille Z. McAvoy , Stephen L. Buchwald
DOI: 10.1021/OL301700Y
关键词: Selectivity 、 Alkyl 、 Organic chemistry 、 Chemistry 、 Palladium 、 Aldehyde 、 Aryl 、 Molecule 、 One-pot synthesis 、 Catalysis
摘要: A method for the Pd-catalyzed N-arylation of both aryl and alkyl amidines with a wide range bromides, chlorides, triflates is described. The reactions proceed in short reaction times excellent selectivity monoarylation. one-pot synthesis quinazoline derivatives, via addition an aldehyde to crude mixture following N-arylation, also demonstrated.
acs.org
sci-hub.se 参考文章(28)
Mariappan Anbazhagan, Chad E Stephens, David W Boykin, Palladium-catalyzed N-arylation of O-methylamidoximes Tetrahedron Letters. ,vol. 43, pp. 4221- 4224 ,(2002) , 10.1016/S0040-4039(02)00775-X
Paul Renton, Brenda Green, Shawn Maddaford, Suman Rakhit, John S. Andrews, NOpiates: Novel Dual Action Neuronal Nitric Oxide Synthase Inhibitors with μ-Opioid Agonist Activity. ACS Medicinal Chemistry Letters. ,vol. 3, pp. 227- 231 ,(2012) , 10.1021/ML200268W
James Barker, Melvyn Kilner, The coordination chemistry of the amidine ligand Coordination Chemistry Reviews. ,vol. 133, pp. 219- 300 ,(1994) , 10.1016/0010-8545(94)80059-6
P.J. Dunn, Amidines and N -Substituted Amidines ChemInform. ,vol. 5, pp. 655- 699 ,(2005) , 10.1016/B0-08-044655-8/00109-4
Xiaohu Deng, Neelakandha S. Mani, Reactivity-Controlled Regioselectivity: A Regiospecific Synthesis of 1,2-Disubstituted Benzimidazoles European Journal of Organic Chemistry. ,vol. 2010, pp. 680- 686 ,(2010) , 10.1002/EJOC.200901056
Michael E Kort, Irene Drizin, Robert J Gregg, Marc JC Scanio, Lei Shi, Michael F Gross, Robert N Atkinson, Matthew S Johnson, Gregory J Pacofsky, James B Thomas, William A Carroll, Michael J Krambis, Dong Liu, Char-Chang Shieh, XuFeng Zhang, Gricelda Hernandez, Joseph P Mikusa, Chengmin Zhong, Shailen Joshi, Prisca Honore, Rosemarie Roeloffs, Kennan C Marsh, Bernard P Murray, Jinrong Liu, Stephen Werness, Connie R Faltynek, Douglas S Krafte, Michael F Jarvis, Mark L Chapman, Brian E Marron, None, Discovery and biological evaluation of 5-aryl-2-furfuramides, potent and selective blockers of the nav1.8 sodium channel with efficacy in models of neuropathic and inflammatory pain Journal of Medicinal Chemistry. ,vol. 51, pp. 407- 416 ,(2008) , 10.1021/JM070637U
Hua Fu, Liming Hu, Yuyang Jiang, Yufen Zhao, Daoshan Yang, Hongxia Liu, Haijun Yang, Copper‐Catalyzed Synthesis of 1,2,4‐Benzothiadiazine 1,1‐Dioxide Derivatives by Coupling of 2‐Halobenzenesulfonamides with Amidines Advanced Synthesis & Catalysis. ,vol. 351, pp. 1999- 2004 ,(2009) , 10.1002/ADSC.200900101
Daoshan Yang, Hua Fu, Liming Hu, Yuyang Jiang, Yufen Zhao, Copper-Catalyzed Synthesis of Benzimidazoles via Cascade Reactions of o-Haloacetanilide Derivatives with Amidine Hydrochlorides Journal of Organic Chemistry. ,vol. 73, pp. 7841- 7844 ,(2008) , 10.1021/JO8014984
Thomas Wiglenda, Ingo Ott, Brigitte Kircher, Petra Schumacher, Daniela Schuster, Thierry Langer, Ronald Gust, Synthesis and Pharmacological Evaluation of 1H-Imidazoles as Ligands for the Estrogen Receptor and Cytotoxic Inhibitors of the Cyclooxygenase Journal of Medicinal Chemistry. ,vol. 48, pp. 6516- 6521 ,(2005) , 10.1021/JM050190U
Meredeth A. McGowan, Jaclyn L. Henderson, Stephen L. Buchwald, Palladium-Catalyzed N-Arylation of 2-Aminothiazoles Organic Letters. ,vol. 14, pp. 1432- 1435 ,(2012) , 10.1021/OL300178J