The Rh-catalyzed reactions of N-pyridinyl enaminones with internal alkynes leading to the synthesis of iminopyranes via a key C-H bond activation and subsequent tautomeric O-H bond cleavage are reported. Moreover, the pyridine ring in the amino group acts as an auxiliary monodentate site for this annulation and can be easily removed by a simple hydrolysis to afford pyranones.