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Site selectivity in reactions of hydrazonoyl halides with heterocycles containing amino and thione groups leading to fused heterocycles of potential antimicrobial activity

Russian Journal of Bioorganic Chemistry volume 40, pages 106–113 (2014)Cite this article

Abstract

Reaction of hydrazonoyl halides with 6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one and 2,3-diaminoquinazolin-4-one site-selectively afforded 3-substituted-7-(benzylidenamino)-1-phenyl-[1,2,4]triazolo[4,3-a]-pyrimidin-5(1H)-ones, [1,2,4,5]tetrazino[6,1-b]quinazolin-6(4H)-one, and 3-methyl-2-(4-substituted-phenylhydrazo)-[1,2,4]triazino[3,2-b]quinazolin-10-ones in good yields. The structures of the newly synthesized compounds were elucidated by chemical evidence and their IR, 1H, 13C NMR, and MS spectra. Furthermore, some of the products were screened against different strains of bacteria and fungi.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Taif University, P.O. 888, Taif, Saudi Arabia

    M. E. A. Khalifa, M. A. Amin & M. A. N. Mosselhi

  2. Department of Chemistry, Faculty of Science, Suez Canal University, Ismailia, Egypt

    M. A. Amin

  3. Department of Chemistry, Faculty of Science, Cairo University, 12613, Giza, Egypt

    M. A. N. Mosselhi

Authors
  1. M. E. A. Khalifa
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  2. M. A. Amin
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  3. M. A. N. Mosselhi
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Correspondence to M. A. N. Mosselhi.

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Khalifa, M.E.A., Amin, M.A. & Mosselhi, M.A.N. Site selectivity in reactions of hydrazonoyl halides with heterocycles containing amino and thione groups leading to fused heterocycles of potential antimicrobial activity. Russ J Bioorg Chem 40, 106–113 (2014). https://doi.org/10.1134/S1068162014010075

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  • DOI: https://doi.org/10.1134/S1068162014010075

Keywords

  • hydrazonoyl halide
  • site-selectivity
  • quinazoline
  • pyrimidine
  • antimicrobial activity