Huisgen cycloaddition reaction of C-alkynyl ribosides under micellar catalysis: synthesis of ribavirin analogues.
Carbonated analogues of ribavirin were synthesized from ethyl C-ribosylpropiolate obtained by an alkynylation reaction mediated by indium(0). The C-ribosides were then engaged in a Huisgen 1,3-dipolar cycloaddition reaction under a micellar catalysis. In these conditions, formation of 1,2,3-triazoles with control of the regioselectivity was observed. The regiochemistry of the adducts was determined by HMBC 2D-NMR analysis.
Université de Cergy-Pontoise, UMR CNRS 8123, Laboratoire de Synthèse Organique Sélective et Chimie Organométallique, F-95000 Cergy-Pontoise Cedex, France.
Ramzi Aït
RA
Youcef
Mickaël
M
Dos Santos
Sandrine
S
Roussel
Jean-Pierre
JP
Baltaze
Nadège
N
Lubin-Germain
Jacques
J
Uziel
D000998:Antiviral Agents / Q000138:chemical synthesis; D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D008823:Micelles; D015394:Molecular Structure; D012254:Ribavirin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D012266:Ribose / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis
D000998:Antiviral Agents; D008823:Micelles; D014230:Triazoles; D012254:Ribavirin; D012266:Ribose