A general synthesis of C6-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 N1-oxide. The regioselective transmetallation of unsymmetrical dihalopyridines with iPrMgCl allowed C6-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.
Synthesis ofC6-Pyridylpurine Nucleosides by Reaction of NebularineN1-Oxide with Pyridinyl Grignard Reagents / D'Errico, Stefano; Oliviero, Giorgia; Borbone, Nicola; Nici, Fabrizia; Piccialli, Vincenzo; Pinto, Brunella; D'Alonzo, Daniele; Mayol, Luciano; Piccialli, Gennaro. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2015:10(2015), pp. 2244-2249. [10.1002/ejoc.201403648]
Synthesis ofC6-Pyridylpurine Nucleosides by Reaction of NebularineN1-Oxide with Pyridinyl Grignard Reagents
D'ERRICO, STEFANO;OLIVIERO, GIORGIA
;BORBONE, NICOLA;NICI, FABRIZIA;PICCIALLI, VINCENZO;PINTO, BRUNELLA;D'ALONZO, DANIELE;MAYOL, LUCIANO;PICCIALLI, GENNARO
2015
Abstract
A general synthesis of C6-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 N1-oxide. The regioselective transmetallation of unsymmetrical dihalopyridines with iPrMgCl allowed C6-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.File | Dimensione | Formato | |
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