Practical Pd/C-Catalysed Suzuki-Miyaura Reactions for the Preparation of 3-Aryl-4-oxypyridin-2(1H)-ones, 3-Aryl-2,4-oxypyridines and 3-Aryl-2,4-oxyquinolines as Useful Intermediates for the Synthesis of Biologically Active Compounds

被引:16
|
作者
Lamblin, Marc [2 ]
Bares, Hugo [3 ]
Dessolin, Jean [2 ]
Marty, Christel [4 ]
Bourgougnon, Nathalie [4 ]
Felpin, Francois-Xavier [1 ]
机构
[1] Univ Nantes, CNRS UMR 6230, CEISAM, UFR Sci & Tech, F-44322 Nantes 3, France
[2] Univ Bordeaux, CNRS UMR 5248, CBMN, IECB, F-33607 Pessac, France
[3] Univ Bordeaux, UMR CNRS 5255, Inst Sci Mol, F-33405 Talence, France
[4] Univ Bretagne Sud, PRES Univ Europeenne Bretagne, Lab Biotechnol & Chim Marines, F-56017 Vannes, France
关键词
Heterogeneous catalysis; Palladium; Cross-coupling; Nitrogen heterocycles; Nucleosides; Medicinal chemistry; Antiviral agents; REDUCTION-CYCLIZATION HRC; COUPLING REACTIONS; PALLADIUM CATALYSTS; ARYLBORONIC ACIDS; ARYL CHLORIDES; HECK; CARBON; WATER; SALTS;
D O I
10.1002/ejoc.201200721
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Practical heterogeneous Pd/C-catalysed SuzukiMiyaura cross-coupling reactions of 3-iodo-4-oxypyridin-2(1H)-ones, 3-iodo-2,4-oxypyridines, and 3-iodo-2,4-oxyquinolines with arylboronic acids are described as a useful and efficient alternative to homogeneous conditions. The methodology features ligand-free and environmentally friendly conditions, and tolerates a wide range of boronic acids. The cross-coupled products can be viewed as useful intermediates for the preparation of 3-aryl-4-hydroxypyridin-2(1H)-ones, which can be used as new nucleobases for antiherpetic agents.
引用
收藏
页码:5525 / 5533
页数:9
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