Functionalised chromanone (4) is prepared by the condensation of aryldiazonium salt (2) and enaminones (1) in ethanol at room temperature. The structure of (4) was determined by spectral (IR, 1H and 13C NMR), elemental and X-ray diffraction analysis. Compound 4 (C18H15N3O3) crystallizes in the monoclinic space group P21/c with a = 7.9182(5), b = 21.729(2), c = 9.6217(7) Å, β = 97.293(6)°, V = 1642.0(2) Å3, Z = 4. The molecule of compound (4) is bent at the C-16 atom with a C15–O2–C16–C8 torsion angle of 46.18(3)°. Intramolecular phenolic N–H···O hydrogen bonds are also formed. Intermolecular hydrogen bonding and π–π stacking hold the molecules together. The average distance between stacked benzene ring planes is 4.488(12) Å. The preliminary POM analyses of 4 confirm the coexistence of two combined antibacterial and antiparasite pharmacophore sites. Therefore, compound 4 is promising and it should be screened without hesitation against virulent and pathogenic biotargets.
Research on Chemical Intermediates – Springer Journals
Published: Jul 9, 2015
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