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Synthesis, Characterization, and DFT Calculations of Quinoline and Quinazoline Derivatives

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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.

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Authors and Affiliations

  1. Research Institute of Medicinal and Aromatic Plants, Beni-Suef University, 62511, Beni-Suef City, Egypt

    H. S. Mohamed

  2. Department of Chemistry, Faculty of Science, Beni-Suef University, 62511, Beni-Suef, Egypt

    M. K. Abdel-Latif & S.A. Ahmed

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  1. H. S. Mohamed
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Mohamed, H.S., Abdel-Latif, M.K. & Ahmed, S. Synthesis, Characterization, and DFT Calculations of Quinoline and Quinazoline Derivatives. Russ J Org Chem 56, 1660–1668 (2020). https://doi.org/10.1134/S1070428020090250

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