Reactivity models of 1-N-vinyluracil and synthesis of a new class of potential antiviral agents by the use of 1,3-dipolar cycloaddition reactions.
By the use of a convergent approach based on 1,3-dipolar cycloaddition reactions between N-protected formylnitrones generated in situ and 1-N-vinyluracil, a new class of 4'-aza-analogues of 2',3'-dideoxynucleosides is synthesized. Competitive reaction for the endocyclic bond of uracil also brings to a new isoxazolidine derivative fused with the pyrimidine nucleus.
Colacino
E
E
Dipartimento di Chimica, Università della Calabria, Arcavacata di Rende, (CS), Italy. eveline.colacino@mailcity.com
De Luca
G
G
Liguori
A
A
Napoli
A
A
Siciliano
C
C
Sindona
G
G
D000998:Antiviral Agents / Q000138:chemical synthesis*; D002625:Chemistry, Organic / Q000379:methods; D015195:Drug Design; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D014753:Vinyl Compounds / Q000138:chemical synthesis
D000998:Antiviral Agents; D007202:Indicators and Reagents; D014753:Vinyl Compounds; D014498:Uracil