A 'click chemistry' approach to the straightforward synthesis of new 4-aryl-1,2,3-triazolocarbanucleosides

Abstract

The synthesis and biological evaluation as antiviral agents of a series of racemic 4-aryl-1,2,3-triazolyl carbanucleosides of type (±)-10/(±) -11 related to the broad spectrum antiviral agent ribavirin 1 are described. These compounds were produced using a "click chemistry" strategy starting from readily available protected alcohol 13b. The synthetic approach made use of olefinbased organic reactions for the stereoselective construction of the appropriately functionalized cyclopentane ring moiety followed by copper (I) catalyzed Huisgen 1,3-dipolar cycloaddition of azides and alkynes for the regioselective construction of the heterocyclic triazole moiety.