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We report an easy and adaptable multicomponent synthesis of 4H-pyran molecule, namely isobutyl 6-amino-5-cyano-4-(1-(4-isobutylphenyl)ethyl)-2-methyl-4H-pyran-3-carboxylate (IIP). The strategy involves the one-pot three component reaction of 2-(4-isobutylphenyl)propanal, malononitrile, isobutyl acetoacetate and BF3:OEt2 as a catalyst in ethanol under hot condition. The good yield of the product obtained makes this reaction highly efficient for the synthesis of 4H-pyran molecule. The molecular structure of the title compound was investigated using spectral techniques such as FT-IR, 1H NMR, 13C NMR and HR-Mass spectra. Single crystal X-ray structural analysis of the title compound, evidences the “flattened-boat” conformation of pyran ring. Vibrational spectrum and HOMO-LUMO of the title compound have been investigated by computational method using DFT-B3LYP with 6–311++G(d,p) basis set. The calculated geometrical parameters and vibrational frequencies were in good agreement with experimental values. |
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