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Synthesis, Spectral Characteristics, and Biological Activity of 1,3-Oxazepines and 1,3-Oxazepanes Derived from 6-Nitrobenzothiazol-2-amine

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Abstract

1,3-Oxazepine and 1,3-oxazepane derivatives of 6-nitrobenzothiazol-2-amine were synthesized, and their spectral and antibacterial properties were studied. The condensation of 6-nitrobenzothiazol-2-amine with aromatic aldehydes gave the corresponding Schiff bases, whose subsequent intermolecular cyclization with maleic and succinic anhydrides led to the target 1,3-oxazepine and 1,3-oxazepane derivatives. The compositions and structures of the synthesized compounds were established by elemental analysis and FTIR and 1H NMR spectroscopy. 2-(4-Hydroxy-3-methoxyphenyl)-3-(6-nitrobenzothiazol-2-yl)-1,3-oxazepane-4,7-dione and 2-(4-iso-propylphenyl)-3-(6-nitrobenzothiazol-2-yl)-1,3-oxazepane-4,7-dione showed the highest antibacterial activity against the gram-positive bacteria Klebsiellapneumonia and Bacillussubtilis, and the gram-negative bacteria Staphylococcusaureus provide to be highly sensitive to 2-(4-hydroxy-3-methoxyphenyl)-3-(6-nitrobenzothiazol-2-yl)-1,3-oxazepane-4,7-dione.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, University of Kerbala, 56001, Kerbala, Iraq

    S. K. Abbas, H. D. Hanoon & S. M. Radhi

  2. Department of Biology, College of Science, 56001, University of Kerbala, Iraq

    Z. F. Abbas & K. A. Hussein

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  1. S. K. Abbas
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  2. H. D. Hanoon
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  3. Z. F. Abbas
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Correspondence to H. D. Hanoon.

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Abbas, S.K., Hanoon, H.D., Abbas, Z.F. et al. Synthesis, Spectral Characteristics, and Biological Activity of 1,3-Oxazepines and 1,3-Oxazepanes Derived from 6-Nitrobenzothiazol-2-amine. Russ J Org Chem 56, 327–331 (2020). https://doi.org/10.1134/S1070428020020244

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  • DOI: https://doi.org/10.1134/S1070428020020244

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