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

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 N-substituted carbazates. The aza-heterocycles were obtained
with high levels of chemoselectivity and excellent yields.