Abstract
Several 2-glycosylaminopyridines 7, were synthesized through a tandem Diels-Alder/Retro Diels-Alder (DA/RDA) reaction starting from 6-glycosylaminopyrimidines, 6, with dimethyl acetylenedicarboxylate (DMAD) as dienophile. This approach represents a new method for the synthesis of 2-aminopyridine nucleoside analogues. The compounds were tested for their antiviral activity but did not prove active. Several 2-glycopyranosylaminopyridines, 7, (X=O, S;R=H, CH 2OAc) and 2-furanosylaminopyridines were easily prepared from 6-glycosylaminopyrimidines 6 and Dimethyl acetylenedicarboxylate (DMAD) through Diels-Alder/Retro Diels-Alder reaction. No anomerization was observed in those reactions. Antiviral tests were performed with the newly synthesized compounds. [Display omitted]
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