A Rh(III)-catalyzed C-H activation/annulation with an imidazolone as alkene partner is reported to access dihydroisoquinolone-fused imidazolin-2-ones. These bicycles are reminiscent of scaffolds belonging to the pyrrole alkaloid family of natural products. This approach facilitates construction of a variety of urea-fused dihydroisoquinolone scaffolds including heterocyclic moieties.