In the present investigation, an efficient and green synthesis of an intriguing array of structurally novel quinoline‐based α‐arylidene cycloketones i. e., (Z)‐3‐arylidene/ferrocenylmethylene‐5‐methyl/phenyl‐1H‐pyrano[3,4‐b]quinolin‐4(3H)‐ones (6 a‐z, 6 aa and 6 ab) has been successfully accomplished involving solvent‐free reaction between pyrano[3,4‐b]quinolin‐4(3H)‐ones (7 a‐b) and various aromatic aldehydes by simple hand‐grinding in a mortar and pestle using KOH as base at room temperature. The synthetic strategy has the attractive features such as experimental simplicity, mild and environmentally benign reaction conditions, easy work‐up procedure and good yields. A primary screening for their in vitro inhibitory activities against cancer cell lines A549, HT29 and T‐24 revealed that compounds 6 g and 6 t containing 3,4,5‐trimethoxyphenyl moiety showed promising antitumor activity against A549 (IC50 = 3.68 ± 0.69 and 4.82 ± 0.19 μmol•mL−1) and HT29 (IC50 = 6.69 ± 1.16 and 7.69 ± 0.64 μmol•mL−1.

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