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New fluorescent 3H-imidazo[4,5-e][2,1]benzoxazoles: synthesis, spectroscopic characterization, and antibacterial activity

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Chemistry of Heterocyclic Compounds Aims and scope

The new fluorophores of the 3H-imidazo[4,5-e][2,1]benzoxazoles series were synthesized by the regioselective nitration of 3-alkyl-8-phenyl-3H-imidazo[4,5-e][2,1]benzoxazoles. The latter compounds were obtained from the reaction of 1-alkyl-5-nitro-1Hbenzimidazoles with benzyl cyanide in basic MeOH solution. The structures of synthesized compounds were established using spectral (UV-vis, IR, 1H NMR, 13C NMR, and NOESY) and analytical data. Furthermore, it was found that these fluorophores underwent thermal rearrangement to new 5H-imidazo[4,5-f][2,1,3]benzoxadiazole 3-oxides in AcOH in moderate yields. The fluorescence properties and antibacterial activities of new compounds against Gram-positive and Gram-negative bacterial species were also studied.

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Authors and Affiliations

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    Mitra Rezazadeh, Mehdi Pordel & Abolghasem Davoodnia

  2. Buali Research Institute, Ferdowsi Blvd. Buali Sq., Mashhad, Iran

    Sattar Saberi

Authors
  1. Mitra Rezazadeh
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  2. Mehdi Pordel
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  3. Abolghasem Davoodnia
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  4. Sattar Saberi
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Correspondence to Mehdi Pordel.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 918–922

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Rezazadeh, M., Pordel, M., Davoodnia, A. et al. New fluorescent 3H-imidazo[4,5-e][2,1]benzoxazoles: synthesis, spectroscopic characterization, and antibacterial activity. Chem Heterocycl Comp 51, 918–922 (2015). https://doi.org/10.1007/s10593-015-1796-0

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  • DOI: https://doi.org/10.1007/s10593-015-1796-0

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