Synthesis, Characterization, and DFT Calculations of Quinoline and Quinazoline Derivatives
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ynthesis, Characterization, and DFT Calculations of Quinoline and Quinazoline Derivatives H. S. Mohameda,*, M. K. Abdel-Latif b, and S.A. Ahmedb a
Research Institute of Medicinal and Aromatic Plants, Beni-Suef University, Beni-Suef City, 62511 Egypt b
Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef, 62511 Egypt *e-mail: [email protected] Received April 15, 2020; revised April 24, 2020; accepted April 28, 2020
Abstract—Treatment of 3-methylcyclohexanone with ethyl formate in the presence of sodium methoxide afforded sodium (2-methyl-6-oxocyclohexylidene)methanolate which reacted with aminopyrazoles, aminotriazole, and aminotetrazole to produce fused quinazoline derivatives; its reactions with cyanothioacetamide, cyanoacetamide, and cyanoacetohydrazide gave tetrahydroquinoline-3-carbonitrile derivatives. The reactions of 8-methyl-2-sulfanyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile with alkylating agents led to the formation of thieno[2,3-b]quinoline derivatives. DFT computational studies of the synthesized compounds were carried out using B3LYP/6−311+G** and HF/6−311+G** approximations. The calculated HOMO and LUMO energies showed that charge transfer occurs in their molecules. Keywords: 3-Methylcyclohexanone, quinoline, quinazoline, DFT, HOMO, LUMO
DOI: 10.1134/S1070428020090250 INTRODUCTION Triazolopyrimidine derivatives are important heterocyclic compounds with diverse applications. 1,2,4- and 1,2,3-Triazolopyrimidines are purine analogs exhibiting valuable therapeutic and pharmacological properties [1–5]. They act as anticancer [6], antitumor [7], anti-inflammatory [8], antibacterial, antifungal [9], and antimalarial agents [10]. [1,2,4]Triazolo[1,5-a]pyrimidines are also used in agricultural chemistry [1, 11–16]. Compounds containing a [1,2,4]triazolo[1,5-a]pyrimidine moiety have been found to show anti-leishmanial [13, 17], antiviral [18–21], anti-HIV [21, 22], anti-HCV [15, 23], hypoglycemic [24], microtubule-stabilizing CNS [25], and hypnotic activities [26]. Computational studies and calculations had been performed for triazolopyrimidine derivatives, Their UV spectra showed the effect of polar and nonpolar solvents on the absorption intensities [27]; UV-Vis spectra of metal complexes with triazolopyrimidines were also studied [28]. The electronic structure and UV-Vis spectrum of a ruthenium(II) complex with a triazolopyrimidine ligand were calculated using the TD–DFT method [29]. The results of B3LYP/6-311+G** molecular orbital studies on anionic and neutral structures of some triazolopyrimidines showed a very good agreement with the experi-
mental X-ray structures for the three most stable neutral forms [30]. Also, the molecular orbital study was performed on different triazolopyrimidine molecules at the DFT B3LYP/6-31G level of theory, and the excited states were calculated using ZINDO/S [1]. Lately, frontier molecular orbitals (HOMO and LUMO) have been used to describe the chemical reactivity. The energy gap between the HOMO and LUMO can be used to determine the k
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