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Analytical Studies of 6-Hydroxy-5-[(2-hydroxy- 6-oxocyclohex-1-en-1-yl)(2-nitrophenyl)methyl]-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

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Abstract

Synthesis of 6-hydroxy-5-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)(2-nitrophenyl)methyl]-1,3-dimethylpyrimidine- 2,4(1H,3H)-dione in a one pot process based on barbituric acid derivatives, 1,3-cyclohexandione and 2-nitrobenzaldehyde in water media involving diethyl amine as a base. The reaction proceeds efficiently, smoothly with high yield. The synthesized compound is characterized by spectral methods and X-ray single crystal diffraction. The ground state molecular geometry of the compound has been calculated using the density functional method (DFT) with 6–311G(d,p) basis set. The calculated characteristics and electronic absorption spectra based on the TD–DFT method demonstrated good agreement with the experimental data. The electronic absorption, frontier molecular orbital analyses (HOMO–LUMO) and nonlinear optical (NLO) properties were also discussed.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia

    A. Barakat, M. Ali & A. M. Al-Majid

  2. Department of Chemistry, Rabigh College of Science and Art, P. O. Box 344, Rabigh, 21911, Saudi Arabia

    S. M. Soliman

  3. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria, 21321, Egypt

    A. Barakat & S. M. Soliman

  4. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh, 11451, Saudi Arabia

    H. A. Ghabbour

  5. Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt

    H. A. Ghabbour

Authors
  1. A. Barakat
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  2. M. Ali
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  3. A. M. Al-Majid
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  4. S. M. Soliman
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Correspondence to A. Barakat.

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Barakat, A., Ali, M., Al-Majid, A.M. et al. Analytical Studies of 6-Hydroxy-5-[(2-hydroxy- 6-oxocyclohex-1-en-1-yl)(2-nitrophenyl)methyl]-1,3-dimethylpyrimidine-2,4(1H,3H)-dione. Russ J Gen Chem 88, 2381–2387 (2018). https://doi.org/10.1134/S107036321811021X

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  • DOI: https://doi.org/10.1134/S107036321811021X

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