Tuning the Annulation Reactivity of Vinyl Azides and Carbazates: A Divergent Synthesis of Aza-pyrimidinones and Imidazoles

Abstract

A divergent cascade annulation has been developed using readily available vinyl azides and carbazates with a wide range of substituents. Vinyl azides were successfully applied as bifunctional partners to prepare aza-pyrimidinones via 6-ring closure with carbazates as well as to construct polyfunctionalized imidazoles via 5-ring closure with <i>N</i>-substituted carbazates. The aza-heterocycles were obtained with high levels of chemoselectivity and excellent yields