The first direct C-H arylation of purine nucleosides

被引:61
作者
Cerna, Igor [1 ]
Pohl, Radek [1 ]
Hocek, Michal [1 ]
机构
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Gilead & IOCB Res ctr, CZ-16610 Prague 6, Czech Republic
关键词
D O I
10.1039/b714253f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pd-catalyzed direct C-H arylation of unprotected purine nucleosides with aryl iodides at position 8 was developed to allow a straightforward single-step introduction of diverse aryl groups.
引用
收藏
页码:4729 / 4730
页数:2
相关论文
共 25 条
[1]   Palladium-assisted routes to nucleosides [J].
Agrofoglio, LA ;
Gillaizeau, I ;
Saito, Y .
CHEMICAL REVIEWS, 2003, 103 (05) :1875-1916
[2]   Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions [J].
Bellina, F ;
Cauteruccio, S ;
Rossi, R .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) :1379-1382
[3]   Regiocontrolled synthesis of 1,2-diaryl-1H-imidazoles by palladium- and copper-mediated direct coupling of 1-aryl-1H-imidazoles with aryl halides under ligandless conditions [J].
Bellina, F ;
Cauteruccio, S ;
Mannina, L ;
Rossi, R ;
Viel, S .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (03) :693-703
[4]   Regioselective synthesis of 1,5-diaryl-1H-imidazoles by palladium-catalyzed direct arylation of 1-aryl-1H-imidazoles [J].
Bellina, F ;
Cauteruccio, S ;
Mannina, L ;
Rossi, R ;
Viel, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3997-4005
[5]   Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides [J].
Bellina, Fabio ;
Calandri, Chiara ;
Cauteruccio, Silvia ;
Rossi, Renzo .
TETRAHEDRON, 2007, 63 (09) :1970-1980
[6]   Efficient one-step synthesis of optically pure (adenin-8-yl)phenylalanine nucleosides [J].
Capek, P ;
Hocek, M .
SYNLETT, 2005, (19) :3005-3007
[7]   Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines [J].
Capek, Petr ;
Pohl, Radek ;
Hocek, Michal .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2278-2284
[8]   Direct C-H arylation of purines:: Development of methodology and its use in regioselective synthesis of 2,6,8-trisubstituted purines [J].
Cerna, Igor ;
Pohl, Radek ;
Klepetarova, Blanka ;
Hocek, Michal .
ORGANIC LETTERS, 2006, 8 (23) :5389-5392
[9]   Efficient syntheses of C8-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA [J].
Dai, Qing ;
Xu, Daiwang ;
Lim, Keunpoong ;
Harvey, Ronald G. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :4856-4863
[10]   C8-arylguanine and C8-aryladenine formation in calf thymus DNA from arenediazonium ions [J].
Gannett, PM ;
Powell, JH ;
Rao, R ;
Shi, XL ;
Lawson, T ;
Kolar, C ;
Toth, B .
CHEMICAL RESEARCH IN TOXICOLOGY, 1999, 12 (03) :297-304