NEW FLUORESCENT 3<i>H</i>-IMIDAZO[4,5-<i>e</i>][2,1]BENZOXAZOLES: SYNTHESIS, SPECTROSCOPIC CHARACTERIZATION, AND ANTIBACTERIAL ACTIVITY

Authors

  • Mitra Rezazadeh Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
  • Mehdi Pordel Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
  • Abolghasem Davoodnia Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
  • Sattar Saberi Buali Research Institute, Mashhad, Iran

DOI:

https://doi.org/10.1007/2638

Keywords:

3H-imidazo[4, 5-e][2, 1]benzoxazole, 5H-imidazo[4, 5-f][2, 1, 3]benzoxadiazole 3-oxide, emission and absorption spectra, fluorescence, NOESY

Abstract

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-1H-benzimidazoles 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.

How to Cite
Rezazadeh, M.; Pordel, M.; Davoodnia, A.; Saberi, S. Chem. Heterocycl. Compd. 2015, 51, 918. [Khim. Geterotsikl. Soedin. 2015, 51, 918.]

For this article in the English edition see DOI 10.1007/s10593-015-1796-0

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Published

2015-10-29

Issue

Vol. 51 No. 10 (2015)

Section

Original Papers