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
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.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11588/612811
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