Regioselective Palladium(0)-Catalyzed Cross-Coupling Reactions of 5,7-Dichloro-1,6-naphthyridine

被引:9
作者
Ali, Iftikhar [1 ]
Hassan, Zahid [1 ]
Hein, Martin [1 ]
Falodun, Abiodun [1 ,2 ]
Patonay, Tamas [3 ]
Villinger, Alexander [1 ]
Langer, Peter [1 ,4 ]
机构
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Univ Benin, Dept Pharmaceut Chem, Fac Pharm, Benin 30001, Nigeria
[3] Univ Debrecen, Dept Organ Chem, H-4032 Debrecen, Hungary
[4] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany
来源
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 14期
关键词
catalysis; palladium; Suzuki reaction; naphthyridine; regioselectivity; 1,8-NAPHTHYRIDINE DERIVATIVES; BOND FORMATION; INHIBITORS; DISCOVERY; PROFILE; POTENT; ACETYLCHOLINESTERASE/BUTYRYLCHOLINESTERASE; HETEROCYCLES; ANTAGONISTS; RECEPTORS;
D O I
10.1055/s-0032-1316540
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of mono- and diarylated naphthyridine derivatives were prepared by site-selective Suzuki-Miyaura cross-coupling reactions of 5,7-dichloro-1,6-naphthyridine. The first attack occurs at position 5.
引用
收藏
页码:2255 / 2263
页数:9
相关论文
共 34 条
[1]  
Abdelrazek FM., 2010, EUR J CHEM, V1, P368, DOI [10.5155/eurjchem.1.4.368-372.104, DOI 10.5155/EURJCHEM.1.4.368-372.104]
[2]   THE NAPHTHYRIDINES [J].
ALLEN, CFH .
CHEMICAL REVIEWS, 1950, 47 (02) :275-305
[3]   The directed ortho metalation -: cross coupling symbiosis.: Regioselective methodologies for biaryls and heterobiaryls.: Deployment in aromatic and heteroaromatic natural product synthesis [J].
Anctil, EJG ;
Snieckus, V .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) :150-160
[4]   Design, synthesis, and pharmacological profile of novel fused pyrazolo[4,3-d]pyridine and pyrazolo[3,4-b][1,8]naphthyridine isosteres:: A new class of potent and selective acetylcholinesterase inhibitors [J].
Barreiro, EJ ;
Camara, CA ;
Verli, H ;
Brazil-Más, L ;
Castro, NG ;
Cintra, WM ;
Aracava, Y ;
Rodrigues, CR ;
Fraga, CAM .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (07) :1144-1152
[5]   Discovery of Novel 6,6-Heterocycles as Transient Receptor Potential Vanilloid (TRPV1) Antagonists [J].
Blum, Charles A. ;
Caldwell, Timothy ;
Zheng, Xiaozhang ;
Bakthavatchalam, Rajagopal ;
Capitosti, Scott ;
Brielmann, Harry ;
De Lombaert, Stephane ;
Kershaw, Mark T. ;
Matson, David ;
Krause, James E. ;
Cortright, Daniel ;
Crandall, Marci ;
Martin, William J. ;
Murphy, Beth Ann ;
Boyce, Susan ;
Jones, A. Brian ;
Mason, Glenn ;
Rycroft, Wayne ;
Perrett, Helen ;
Conley, Rachael ;
Burnaby-Davies, Nicola ;
Chenard, Bertrand L. ;
Hodgetts, Kevin J. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (08) :3330-3348
[6]  
Brown D. J., 2007, CHEM HETEROCYCLIC CO, V63
[7]   Discovery of 1,6-naphthyridines as a novel class of potent and selective human cytomegalovirus inhibitors [J].
Chan, L ;
Jin, H ;
Stefanac, T ;
Lavallée, JF ;
Falardeau, G ;
Wang, W ;
Bédard, J ;
May, S ;
Yuen, L .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (16) :3023-3025
[8]   A General Palladium Catalyst System for Suzuki-Miyaura Coupling of Potassium Aryltrifluoroborates and Aryl Mesylates [J].
Chow, Wing Kin ;
So, Chau Ming ;
Lau, Chak Po ;
Kwong, Fuk Yee .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) :5109-5112
[9]   Synthesis, Inhibitory Activity of Cholinesterases, and Neuroprotective Profile of Novel 1,8-Naphthyridine Derivatives [J].
de los Rios, Cristobal ;
Egea, Javier ;
Marco-Contelles, Jose ;
Leon, Rafael ;
Samadi, Abdelouahid ;
Iriepa, Isabel ;
Moraleda, Ignacio ;
Galvez, Enrique ;
Garcia, Antonio G. ;
Lopez, Manuela G. ;
Villarroya, Mercedes ;
Romero, Alejandro .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (14) :5129-5143
[10]   Diversity Synthesis of N-Substituted 2-Amino-1,6-naphthyridine Derivatives under Microwave Irradiation [J].
Han, Zheng-Guo ;
Miao, Chun-Bao ;
Shi, Feng ;
Ma, Ning ;
Zhang, Ge ;
Tu, Shu-Jiang .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01) :16-19