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1 2024

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Development, comprehensive characterization, and antimicrobial activity evaluation of a novel class of symmetrical 1,3-benzoxazine derivatives

Issam A.M., Kareem Huda Salah, Jweeg Muhsin Jaber, Mohammed M.N, Abdullah Thamer Adnan, Abdullah Oday I., Hassan Chiya Othman

Polish Journal of Chemical Technology

2024

Vol. 26, nr 4

104--113

Completely symmetrical 6,6’-cyclohexane-1,1-diyl bis (3-substituted-3,4-dihydro-2H-1,3-benzoxazine) synthesized compounds have been able by a two-step process that yields a large amount of the compound. First, phenol and cyclohexanone were subjected to the Friedel-Craft process to produce 1,1’-bis(4-hydroxyphenyl) cyclohexane. The reaction between the bisphenol and formaldehyde and several primary amines produced unique symmetrical 1,3-benzoxazine compounds. Several spectroscopic methods, such as Fourier transform infrared spectroscopy, nuclear magnetic resonance (1H and 13C), GCMS spectrometry, and CHNS, were utilized in conjunction with tridimensional liquid chromatography (TLC) to investigate and validate the structures of the compounds created thoroughly. Two Gram-negative and two Gram-positive bacteria and a pathogenic fungus were tested for antimicrobial activity in contrast to the gold-standard medications streptomycin and nystatin. The antibacterial activity of some of these compounds was even better than that of the gold-standard medications, which is encouraging.