Synthesis of functionalized 1,3‐indandiones containing‐cyclopentenones and ‐benzotropones has been achieved by the reaction of 1,5‐diphenylpenta‐1,4‐diyn‐3‐ones with 1,3‐indandiones, bindone respectively. The developed method involves Michael‐anti‐Michael addition cascade reactions under transition‐metal‐free conditions. This is the first report to synthesise diverse benzotropone fused with 1,3‐indandiones under transition metal‐free conditions from bindone.