Synthesis, Spectral Characteristics, and Biological Activity of 1,3-Oxazepines and 1,3-Oxazepanes Derived from 6-Nitrobenzothiazol-2-amine
Sawsan Khudhair Abbas, H. D. Hanoon, Zainab Abbas, Khalid Ali Hussein, Sajid M.Radhi
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.