Pyridine-N-oxides bearing a pharmacophoric oxadiazole moiety could be C[sbnd]H functionalized via the acid-catalyzed reaction with dialkylcyanamides, providing access to hitherto undescribed pyridine-2-yl substituted ureas, which have potential as “lead-like” scaffolds for medicinal chemistry. Atom-economy, environmental friendliness (no halide-containing or toxic reagents), simple work-up, as well as scalability are the main advantages of the employed procedure.