In summary, we have developed a photochemical methodology for the peripheral editing of the pyridine core that relies on a dearomatization/aromatization strategy. After activation of a pyridine as a Zincke imine intermediate, it reacts with an electrophilic N-centered radical generated from N-aminopyridinium salts in a photochemical manner. The amidoderivative formed, after aromatization, furnishes the desired product. Importantly, the C-N bond formation occurs predominantly at the C3 position. Depending on the nature of the C2-substituent (aryl versus alkyl) in the starting material, C3,C5 or C2,C3 functionalized pyridines are formed. The method is characterized by mild reaction conditions, scalability, pyridine as the limiting reagent, and excellent regioselectivity. Importantly it can be performed in a one-pot fashion.