Synthesis and characterization of new oxazepines derived from D-erythroascorbic acid

Abstract EN

The new schiff bases derived from D-erythroascorbic acid contaning heterocyclic unit were synthesized by condensation of D-erythroascorbic acid with aromatic amine (containing 1, 3, 4- oxadiazole or 1, 3, 4-thiadiazole unit) in dry benzene using glacial acetic acid as a catalyst.

Derythroascorbic acid [IV] was synthesized by four steps (Scheme 1), while the primary aromatic amine which is containing 1, 3, 4-oxadiazole [VII] or 1, 3, 4-thiadiazole [VIII] synthesized by the reaction of 4-methoxy benzoyle hydrazine [VI] with 4-amino benzoic acid or by the reaction tuloic acid with thiosemicarbazide, respectively in the presence of POCl3.

The new 1, 3-oxazepine derivatives were obtained by addition reaction of Schiff bases with different anhydrides in dry benzene, The new 1, 3- oxazepine derivatives [XII]a-d-[XIV]a-d were synthesized by refluxing compound [IX] , [X] or [XI] with different anhydride (maleic, phthalic, naphthalic anhydride or pyromellitic dianhydride) in presence of dry benzene.

The structure of synthesized compounds have been characterized by their melting points, elemental analysis and by their spectral data ; FTIR, UV-Vis, Mass and (1HNMR, 13CNMR of some of them) spectroscopy.

All the synthesized compounds have been screened for their antibacterial activities.

They exhibited good antibacterial activity against Escherichia coli (G-) and Staphylococus aureus (G+).