Synthesis of 4-Aryl-2-aminopyridine Derivatives and Related Compounds

被引：10

作者：

Pavlovic, Vladimir ^{[2
]}

Petkovic, Milos ^{[1
]}

Popovic, Stanimir ^{[1
]}

Savic, Vladimir ^{[1
]}

机构：

[1] Univ Belgrade, Fac Pharm, Belgrade 11000, Serbia

[2] Univ Belgrade, Fac Chem, Belgrade 11000, Serbia

来源：

SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 23期

关键词：

Aminopyridines; aminoquinolines; palladium catalysis; synthesis; BUCHWALD-HARTWIG AMINATION; ARYL CHLORIDES; ACID; AMINOPYRIDINES; COMPLEXES; CATALYST; BROMIDES; BULKY;

D O I：

10.1080/00397910902898601

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short, efficient, and high-yielding synthesis of 4-aryl-2-aminopyridine derivatives has been developed. The route employs two palladium-catalyzed processes, the Suzuki reaction and the Buchwald-Hartwig amination, as the key steps. The same approach has been used for preparation of the corresponding quinoline derivatives. In addition, a brief study of biological properties showed the anticancer potential of these compounds.

引用

页码：4249 / 4263

页数：15

共 28 条

[1] Lewis acid-promoted transformation of 2-alkoxypyridines into 2-aminopyridines and their antibacterial activity. Part 2: Remarkably facile C-N bond formation
Abdel-Aziz, AAM
El-Subbagh, HI
Kunieda, T
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (16) : 4929 - 4935
[2] Directed ortho metalation-boronation and Suzuki-Miyaura cross coupling of pyridine derivatives:: A one-pot protocol to substituted azabiaryls
Alessi, Manlio
Larkin, Andrew L.
Ogilvie, Kevin A.
Green, Laine A.
Lai, Sunny
Lopez, Simon
Snieckus, Victor
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (05) : 1588 - 1594
[3] Concise total syntheses of variolin B and deoxyvariolin B
Anderson, RJ
Hill, JB
Morris, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) : 6204 - 6212
[4] Palladium-catalyzed Buchwald-Hartwig coupling of deactivated aminothiophenes with substituted halopyridines
Begouin, Agathe
Hesse, Stephanie
Queiroz, Maria-Joao R. P.
Kirsch, Gilbert
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (10) : 1678 - 1682
[5] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters
Billingsley, Kelvin
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) : 3358 - 3366
[6] Preparation of new axially chiral bridged 2,2′-bipyridines and pyridyl monooxazolines (pymox).: Evaluation in copper(I)-catalyzed enantioselective cyclopropanation
Bouet, Alexis
Heller, Barbara
Papamicael, Cyril
Dupas, Georges
Oudeyer, Sylvain
Marsais, Francis
Levacher, Vincent
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (09) : 1397 - 1404
[7] Application of fragment screening by X-ray crystallography to the discovery of aminopyridines as inhibitors of β-secretase
Congreve, Miles
Aharony, David
Albert, Jeffrey
Callaghan, Owen
Campbell, James
Carr, Robin A. E.
Chessari, Gianni
Cowan, Suzanna
Edwards, Philip D.
Frederickson, Martyn
McMenamin, Rachel
Murray, Christopher W.
Patel, Sahil
Wallis, Nicola
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (06) : 1124 - 1132
[8] An efficient and general synthesis of 3-substituted propionaldehydes using the Suzuki-Miyaura coupling
Cowden, CJ
Hammond, DC
Bishop, BC
Brands, KMJ
Davies, AJ
Dolling, UH
Brewer, SE
[J]. TETRAHEDRON LETTERS, 2004, 45 (32) : 6125 - 6128
[9] Group 10 metal aminopyridinato complexes: Synthesis, structure, and application as aryl-Cl activation and hydrosilane polymerization catalysts
Deeken, S
Proch, S
Casini, E
Braun, HF
Mechtler, C
Marschner, C
Motz, G
Kempe, R
[J]. INORGANIC CHEMISTRY, 2006, 45 (04) : 1871 - 1879
[10] Octahedral group 4 metal complexes that contain amine, amido, and aminopyridinato ligands: Synthesis, structure, and application in alpha-olefin oligo- and polymerization
Fuhrmann, H
Brenner, S
Arndt, P
Kempe, R
[J]. INORGANIC CHEMISTRY, 1996, 35 (23) : 6742 - 6745

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