Synthesis of C6-Pyridylpurine Nucleosides by Reaction of Nebularine N1-Oxide with Pyridinyl Grignard Reagents

被引：2

作者：

D'Errico, Stefano ^{[1
]}

Oliviero, Giorgia ^{[1
]}

Borbone, Nicola ^{[1
]}

Nici, Fabrizia ^{[1
]}

Piccialli, Vincenzo ^{[2
]}

Pinto, Brunella ^{[1
]}

D'Alonzo, Daniele ^{[2
]}

Mayol, Luciano ^{[1
]}

Piccialli, Gennaro ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Farm, I-80131 Naples, Italy

[2] Univ Naples Federico II, Dipartimento Sci Chim, I-80131 Naples, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 10期

关键词：

Synthetic methods; Grignard reaction; Transmetallation; Nucleosides; Nucleobases; CYTOSTATIC 6-ARYLPURINE NUCLEOSIDES; SOLID-PHASE SYNTHESIS; PHARMACOLOGICAL EVALUATION; C-C; ANALOGS; C-6; 6-HETARYLPURINE; INHIBITORS; DESIGN; ROUTES;

D O I：

10.1002/ejoc.201403648

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general synthesis of C-6-pyridylpurine nucleosides is described. The reported synthetic procedure exploits the regioselective addition of pyridinyl Grignard reagents, obtained by bromine/magnesium exchange between mono- or dihalopyridines and iPrMgCl, to the C6-N1-O- moiety of nebularine N-1-oxide. The regioselective transmetallation of unsymmetrical dihalopyridines with iPrMgCl allowed C-6-halopyridylpurine nucleosides to be obtained through the addition of halopyridinyl Grignard reagents. The presence of a halogenated pyridine ring in these nucleosides allows for further useful synthetic transformations.

引用

收藏

页码：2244 / 2249

页数：6

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