Novel bis‐chromeno[2,3‐b]pyridine derivatives were synthesized with good yields by a clean and efficient methodologies involving one‐pot three‐component synthesis of bis‐aldehydes, malononitrile dimer, and dimedone in the presence of piperidine as a catalyst in EtOH. Depending on the length and position of the spacer in the bis‐aldehyde derivatives 1, the reactions proceeded to give either the bis(2,4‐diamino‐tetrahydro‐5H‐chromeno[2,3‐b]pyridine‐3‐carbonitriles) 4 or bis(4‐amino‐2,6‐dioxo‐hexahydro‐2H‐chromeno[2,3‐b]pyridine‐3‐carbonitriles) 5. All of the new compounds have been characterized by spectral data.