European Journal of Chemistry 2017, 8(4), 358-366 | doi: https://doi.org/10.5155/eurjchem.8.4.358-366.1632 | Get rights and content

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Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives


Hany Mostafa Mohamed (1) , Ashraf Hassan Fekry Abd El-Wahab (2,*) , Tarek Maamon El-Gogary (3)

(1) Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom Saudi Arabia
(2) Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom Saudi Arabia
(3) Chemistry Department, Faculty of Science (Domyat), Damietta University, 34517, Domyat Al-Gideda, Egypt
(*) Corresponding Author

Received: 21 Jul 2017 | Revised: 23 Aug 2017 | Accepted: 04 Sep 2017 | Published: 31 Dec 2017 | Issue Date: December 2017

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.


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Keywords


Malononitrile; Fukui functions; Ethyl cyanoacetate; 4-Phenyldiazenyl-1-naphthol; 4H-Naphthopyran derivatives; Density Functional Theory (DFT)

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DOI: 10.5155/eurjchem.8.4.358-366.1632

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Funding information


Jazan University, 2097, Jazan, Kingdom Saudi Arabia.

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How to cite


Mohamed, H.; Abd El-Wahab, A.; El-Gogary, T. Eur. J. Chem. 2017, 8(4), 358-366. doi:10.5155/eurjchem.8.4.358-366.1632
Mohamed, H.; Abd El-Wahab, A.; El-Gogary, T. Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives. Eur. J. Chem. 2017, 8(4), 358-366. doi:10.5155/eurjchem.8.4.358-366.1632
Mohamed, H., Abd El-Wahab, A., & El-Gogary, T. (2017). Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives. European Journal of Chemistry, 8(4), 358-366. doi:10.5155/eurjchem.8.4.358-366.1632
Mohamed, Hany, Ashraf Hassan Fekry Abd El-Wahab, & Tarek Maamon El-Gogary. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives." European Journal of Chemistry [Online], 8.4 (2017): 358-366. Web. 28 May. 2023
Mohamed, Hany, Abd El-Wahab, Ashraf, AND El-Gogary, Tarek. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

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