• Title/Summary/Keyword: 2,4,5-Trisubstituted imidazoles

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Zinc (II) [tetra(4-methylphenyl)] Porphyrin: a Novel and Reusable Catalyst for Efficient Synthesis of 2,4,5-trisubstituted Imidazoles Under Ultrasound Irradiation

  • Safari, Javad;Khalili, Shiva Dehghan;Banitaba, Sayed Hossein;Dehghani, Hossein
    • Journal of the Korean Chemical Society
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    • v.55 no.5
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    • pp.787-793
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    • 2011
  • An efficient three-component one-step synthesis of 2,4,5-trisubstituted imidazoles by condensation reaction of 1,2-diketones or ${\alpha}$-hydroxyketones with aromatic aldehydes and ammonium acetate using Zinc (II) [tetra (4-methylphenyl)] porphyrin as a novel and reusable catalyst under ultrasound irradiation at ambient temperature is described. In this method, ${\alpha}$-hydroxyketones as well as 1,2-diketones were converted to their corresponding 2,4,5-trisubstituted imidazoles in excellent yields.

A Fast, Highly Efficient and Green Protocol for One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles Catalyzed by [TBA]2[W6O19] as a Reusable Heterogeneous Catalyst

  • Ashrafi, Mozhgan;Davoodnia, Abolghasem;Tavakoli-Hoseini, Niloofar
    • Bulletin of the Korean Chemical Society
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    • v.34 no.5
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    • pp.1508-1512
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    • 2013
  • A simple and efficient synthesis of 2,4,5-trisubstituted imidazoles was achieved via a one-pot three-component cyclocondensation of benzil, aromatic aldehydes, and ammonium acetate in the presence of a catalytic amount of tetrabutylammonium hexatungstate $[TBA]_2[W_6O_{19}]$ as a heterogeneous catalyst under thermal solvent-free conditions. The key features of this methodology are operational simplicity, high yields, short reaction times, and a recyclable catalyst with a very easy work up.

Synthesis, Docking Study and In-vitro Evaluation of Anti-Tuberculosis Activity of Tri Substituted Imidazoles Containing Quinoline Moiety

  • Sahana, S.;Vijayakumar, G.R.;Sivakumar, R.;Sriram, D.;Saiprasad, D.V.
    • Journal of the Korean Chemical Society
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    • v.66 no.3
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    • pp.194-201
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    • 2022
  • A simple, efficient, and cost-effective method has been employed for the synthesis of 2,4,5-trisubstituted imidazole derivatives (3a-j) containing quinoline substituent at 2nd position. Title compounds were obtained by multicomponent reaction (MCR), involving aryl substituted 1,2-diketone, quinoline carbaldehyde and ammonium acetate in the presence of acetic acid solvent under mild reaction conditions. The newly synthesized quinoline containing imidazole derivatives were confirmed through FT-IR, 1H-NMR, 13C-NMR and mass spectral analysis. In-vitro microplate alamar blue assay (MABA) to determine the MIC (minimum inhibitory concentration) values against Mycobacterium tuberculosis H37Rv was performed for the synthesized compounds. The synthesized compounds exhibited activity against Mycobacterium tuberculosis and among which compounds, 3d, 3f and 3i showed good activity. The highest activity was showed with compound 3i. The anti-mycobacterial activity results are well correlated with the computational molecular docking analysis, which was performed for the synthesized compounds prior to the evaluation of the activity.