Reagent‐controlled chemo‐ and regioselective reduction of 5,15‐diazaporphyrins has been developed. The selective reduction of carbon–carbondoublebonds of diazaporphyrins provides 18 π aromatic isobacteriochlorin‐type products, whereas the reduction of carbon–nitrogendoublebonds leads to selective formation of 20 π N,N′‐dihydrodiazaporphyrins in excellent yields. The distinct antiaromatic character