Click synthesis of N1-(β-D-ribofuranosyl)-C4-(coumarin-4"-yl)-1,2,3-triazoles

A series of eight N-1-(beta-D-ribofuranosyl)-C-4-(coumarin-4 ''-yl)-1,2,3-triazoles have been synthesized by Cu(I)-catalyzed click reaction of 1-azido-1-deoxy-2,3,5-tri-O-benzoyl-beta-D-ribofuranose with differently substituted 4-ethynylcoumarins followed by debenzoylation of the resulted N-1-(2 ',3 ',5 '-tri-O-benzoyl-beta-D-ribofuranosyl)-C-4-(coumarin-4 ''-yl)-1,2,3-triazoles in 71 to 89% overall yields. The structures of all the synthesized compounds were established on the basis of their spectral data analysis that was further confirmed by X-ray data analysis of one of the model benzoylated compounds, i.e. N-1-(2 ',3 ',5 '-tri-O-benzoyl-beta-D-ribofuranosyl)-C-4-(7 ''-isopropoxycoumarin-4 ''-yl)-1,2,3-triazole.