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.