Preparation, characterization and biological activity of some new seven-membered heterocyclic compounds

Abstract

Introduction: The synthesis of Schiff base has huge importance to prepare a lot of heterocyclic compounds, Oxazepines can be prepared by reaction of imine compounds with anhydrides to obtain seven-membered heterocyclic compound. Materials and Methods: A series of 1, 3-oxazepine derivatives were prepared, firstly preparation of the imines (S1-S2) from reaction of 2-chlorobenzaldehyde with each of p-toluidine and 4, 4’-Methylenedianiline and using glacial acetic acid as a catalyst. The second step involves the reaction of prepared Schiff bases (S1-S2) with both 3-nitrophthalic anhydride and Itaconic anhydride in dry benzene to produce 1,3-oxazepine derivatives (OX1-OX4), The antibacterial activity determined by using Agar well diffusion procedure method, against two types of bacteria, which it gram-positive (Staphylococcus aureus) and gram-negative (Escherichia coli). Results and Discussion: Oxazepine compounds are formed through Pericyclic reactions which are concerted processes that pass through a single cyclic transition state structure involving simultaneously breaking and formation of bonds. The compounds were identified by using FT-IR and NMR technology. Conclusions: The possibility of preparing some mono-chelating and bi-chelating Schiff bases derived from the reaction of 2-chlorophenzaldehyde with different aromatic primary amines and preparing some of the new oxazepine compounds through the reaction of the Schiff bases with different anhydrides in benzene, which can be used to extract metal ions from their solutions. The biochemical efficacy of compounds demonstrated that their ability to inhibit Staphylococcus aureus was greater compared with the ability to inhibit Escherichia coli.