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The synthesis of novel isoxazolo[5,4‐b]pyrano[2,3‐f]quinoline hybrids has been achieved through a one‐pot three‐component reaction of 3‐methyl‐7,8‐dihydroisoxazolo[5,4‐b]quinolin‐5(6H)‐one, isatins or aromatic aldehydes and malononitrile in the presence of a base at ambient temperature. The reaction occurred through a domino Knoevenagel‐Michael type addition‐O‐cyclization sequence in a single transformation to afford the products in excellent yields. One of the isoxazolo[5,4‐b]pyrano[2,3‐f]quinoline was found to be highly sensitive towards picric acid with a lower limit of detection of 1.2 μM and quenching constant of 2.02×103 M−1 [ABSTRACT FROM AUTHOR]