Herein, an iron‐catalyzed protocol for the aromatization‐driven deconstruction and decarboxylation of ketone‐derived dihydroquinazolinones in reaction with unsaturated carboxylic acids is reported. A diverse range of fluoroacrylic acids and cinnamic acids reacted effectively with dihydroquinazolinones, yielding essential monofluoroalkenes and alkenes with excellent stereoselectivity. Additionally, spiro‐dihydroquinazolinones served as suitable substrates, facilitating the synthesis of valuable quinazolin‐4(3H)‐ones featuring alkene motifs. This protocol is notable for its operational simplicity and versatility, enabling the chemical diversification of active molecules.