Abstract
A one pot three component reaction of 4-phenyldiazenyl-1-naphthol (1), p -chloro benzaldehyde (2) and malononitrile or ethyl cyanoacetate (3) in ethanol/piperidine under reflux afforded 2-amino-4-( p -chlorophenyl)-6-phenyldiazenyl-4 H -naphtho[1,2-b]pyrano-3-carbonitrile (4a) and ethyl 2-amino-4-( p -chlorophenyl)-6-phenyldiazenyl-4 H -naphtho[1,2-b]pyrano -3-carboxylate (4b). Structure of these compounds was established on the basis of IR, 1 H NMR, 13 C NMR, Mass and UV-Vis spectra. Molecular geometry of compounds 4a and b was obtained at B3LYP/6-31+G(d) level. Two tautomers and two conformers were geometrically optimized. The tautomers are separated by about 7.942 kcal/mol while rotational conformers are only separated by 0.511 kcal/mol. Molecular reactivity descriptors including global electrophilicity, hardness, softness and local condensed Fukui functions were computed and discussed. Frontier molecular orbitals (HOMO and LUMO) were also computed.
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