Synthesis, Identification, Biological Evaluation of Seven-membered Heterocyclic Derivatives from 2,3-di Chloroaniline

Abstract

This study?s focus was centered on the synthesis of heterocyclic compounds incorporating a seven-membered ring, specifically 1,3-oxazepine. The initial phase of the synthesis involved the preparation of azo compound (1) through the coupling of the diazonium salt of 2,3-dichloroaniline with 4-bromoacetophenone in an alkaline alcoholic medium. This was then succeeded by the reaction of azo compound (1) with 4-nitroaniline and 4-methoxyaniline in absolute ethanol, employing glacial acetic acid as a catalyst, resulting in Schiff base derivatives (2) and (3), respectively. Subsequent to this, Schiff base (2) was reacted with phthalic anhydride and maleic anhydride, as well as succinic anhydride, in a dehydrated benzene environment, leading to the formation of heterocyclic seven-membered compounds (4), (5), and (6), respectively. Finally, Schiff base (3) was subjected to reaction with phthalic anhydride and maleic anhydride, as well as succinic anhydride, in dry benzene, resulting in the synthesis of heterocyclic seven-membered compounds (7), (8), and (9) respectively. Each of these synthesized compounds underwent characterization through Fourier-transform infrared and proton nuclear magnetic resonance spectroscopic analysis, and the progress of reactions was monitored through Rf and thin-layer chromatography techniques. Melting points were recorded as part of the characterization process. In addition, an investigation into the biological activity of these compounds was conducted against both positive and negative bacterial strains.. KEYWORDS :Azo compounds, Oxazepine, Schiff bases.