Author : Khdeaur Abbas, Sawsan
Synthesis of new bis-1,3-oxazepine-4,7-dione derivatives containing tow azo groups and preliminary evaluation of their antibacterial activity
journal of kerbala university,
2014, Volume 10, Issue 0, Pages 106-138
In this work new bisazo bis -1,3-oxazepine - 4,7- dione derivatives have been synthesized via cycloaddition reaction type [2+5→7] of phthalic and maleic anhydrides to some synthesized bisazoimine derivatives .
ortho-Tolidine was converted to the corresponding bisazoaldehyde derivative 1 via coupling reaction with phenoxide anion of 2-hydroxybenzaldehyde. Aldehyde groups in bisazoaldehyde derivative 1 was condensed with different primary amines and only one hydrazine derivative (cyclohexylamine, phenylhydrazine, 2,4-dimethylaniline, 4-methoxyaniline, aniline and 4-bromoaniline) in presense of glacial acetic acid as catalyst in absolute ethanol to give bis-azoimine derivatives 2a-f respectively. The resulting bisazoimine derivatives 2a-f were then introduced in [2+5→7] cycloaddition reaction with each phthalic and maleic anhydrides in dry benzene to give new bisazo bis-1,3-oxazepine-4,7-dione derivatives 3a-f and 4a-f respectively.
All the synthesized target compounds 3a-f and 4a-f have been characterized by (C.H.N.) elementary micro analysis and the spectroscopic methods including FT-IR , 1H NMR for compounds 3a-e and 4a-e and 13C NMR for compounds (3a, 4a and 4e). The last step included preliminary evaluation of antibacterial activity for all target compounds 3a-f and 4a-f which were tested against Staphylococcus aureous (Gram positive) and Escherichia coli (Gram negative), these activities have been determined in vitro using disc diffusion method (Agar), the results revealed that some of compounds showed measurable activity as shown in table (9).