Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives
- 31 December 2017
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 8 (4), 358-366
- https://doi.org/10.5155/eurjchem.8.4.358-366.1632
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-4H-naphtho[1,2-b]pyrano-3-carbonitrile (4a) and ethyl 2-amino-4-(p-chlorophenyl)-6-phenyldiazenyl-4H-naphtho[1,2-b]pyrano -3-carboxylate (4b). Structure of these compounds was established on the basis of IR, 1H NMR, 13C 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.Keywords
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