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Appl. Sci. 2017, 7(10), 967; doi:10.3390/app7100967

Computational and Experimental Study on Molecular Structure of Benzo[g]pyrimido[4,5-b]quinoline Derivatives: Preference of Linear over the Angular Isomer

1
Grupo/Semillero de Investigación en Compuestos Heterocíclicos, Programa de Química, Facultad de Ciencias Básicas, Universidad del Atlántico, Puerto Colombia, Atlántico, Colombia
2
Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A 25360, Cali, Colombia
3
Centro Nacional de Asistencia Técnica a la Industria (Centro—ASTIN)—SENA, Complejo Salomia, Cali, Colombia
4
Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain
*
Author to whom correspondence should be addressed.
Received: 22 August 2017 / Revised: 11 September 2017 / Accepted: 16 September 2017 / Published: 21 September 2017
(This article belongs to the Section Chemistry)
View Full-Text   |   Download PDF [2386 KB, uploaded 30 September 2017]   |  

Abstract

A series of 5-aryl-2-methylthio-5,12-dihydrobenzo[g]pyrimido[4,5-b]quinoline-4,6,11(3H)-trione was synthesized through an environmental friendly multicomponent methodology and characterized with FT-IR (Fourier Transform infrared spectroscopy), 1H NMR (Nuclear Magnetic Resonance ), 13C NMR and GC-MS (gas chromatography-mass spectrometry). The 5-(4-methoxyphenyl)-2-methylthio-5,12-dihydrobenzo[g]pyrimido[4,5-b]quinoline-4,6,11(3H)-trione 4c compound was characterized by X-ray single crystal diffraction. The geometry of 4c has been fully optimized using DFT (Density functional theory), B3LYP functional and 6-31G(d,p) basis set, thus establishing the ground state energy and thermodynamic features for the mentioned compound, which are in accordance with the experimental data and the crystal structure. The experimental results reveal a strong preference for the regioselective formation of 4c linear four fused rings over the angular four fused and suggest a possible kinetic control in product formation. View Full-Text
Keywords: DFT analysis; MCR’s; MW irradiation; one-pot reactions; quinoline derivatives DFT analysis; MCR’s; MW irradiation; one-pot reactions; quinoline derivatives
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Trilleras, J.; Pacheco, D.J.; Pérez-Gamboa, A.; Quiroga, J.; Ortiz, A.; Gálvez, J.; Nogueras, M.; Cobo, J. Computational and Experimental Study on Molecular Structure of Benzo[g]pyrimido[4,5-b]quinoline Derivatives: Preference of Linear over the Angular Isomer. Appl. Sci. 2017, 7, 967.

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