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Microwave-promoted synthesis and biological activity of some 2-hetarylmethyl-4-(4-hetarylphenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

A series of fused and non-fused 1,2,4-triazole derivatives were prepared starting from ethyl 4-[1-(2-ethoxy-2-oxoethyl)-3-methyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]benzoate. Firstly, both ethyl ester groups were simultaneously transformed into hydrazide groups, then into 4-amino-5-mercapto-4H-1,2,4-triazol-3-yl groups using both microwave-assisted and conventional methods. The latter products interacted with 2 equiv of phenacyl bromides, chloroacetone, or chloroacetic acid to form ring assemblies containing two [1,2,4]triazolo-[3,4-b][1,3,4]thiadiazine fragments. Cyclization using 2 equiv of carboxylic acids, urea, or CS2 leads to the corresponding [1,2,4]triazolo-[3,4-b][1,3,4]thiadiazole derivatives. The synthesized compounds were evaluated in regard to their antimicrobial, anti-lipase, and antiurease activities.

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Scheme 2

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Financial support provided by The Scientific and Technical Research Council of Turkey (TUBİTAK) through project 112T640 is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Recep Tayyip Erdogan University, 53100, Rize, Turkey

    Musa Özil & Osman Bodur

  2. Department of Biology, Recep Tayyip Erdogan University, 53100, Rize, Turkey

    Serdar Ülker

  3. Faculty of Health Sciences, Department of Nutrition and Dietetics, Karadeniz Technical University, Trabzon, Turkey

    Bahittin Kahveci

Authors
  1. Musa Özil
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  2. Osman Bodur
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  3. Serdar Ülker
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  4. Bahittin Kahveci
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Correspondence to Musa Özil.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(1), 88–96

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Özil, M., Bodur, O., Ülker, S. et al. Microwave-promoted synthesis and biological activity of some 2-hetarylmethyl-4-(4-hetarylphenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one derivatives. Chem Heterocycl Comp 51, 88–96 (2015). https://doi.org/10.1007/s10593-015-1664-y

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  • DOI: https://doi.org/10.1007/s10593-015-1664-y

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