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In this study, a simple and efficient method for the synthesis of 1,5-dihydropyrano[2,3-c]chromene derivatives is reported by three component reaction of aromatic aldehydes, malononitrile, and 3-hydroxycoumarin in the presence of piperidine as base in ethanol, under reflux conditions. Also, the experimental results involving new and already synthesized compounds are compared with the theoretical calculations. The energy, molecular electrostatic potential (MEP), HOMO–LUMO energy gap, chemical properties and NMR analyses of 1,5-dihydropyrano[2,3-c]chromene derivatives in DMSO solution were estimated using density functional theory and 6-311++G (d,p) basis set. The solvent effect was explored using the polarizable continuum model (PCM) method. Increasing polarity and having no much difference in energies show the more effects of newly synthesized compounds (R2-DHPC) towards already synthesized compounds (R4-DHPC) in human body. Also, the results display that there is a good agreement between experimental and theoretical data.

Theoretical and experimental investigations into the structural, electronic, and molecular properties of 1,5-dihydropyrano[2,3-c]chromene derivatives