Using A pericyclic Reactions for The Synthesis of New 1,3-Oxazepine Compounds From New Imines

Abstract

In this research new1,3-oxazepine derivatives[6-11] were prepared starting from new Schiff bases [4] and [5]. 5,5'-{[3-(Methoxycarbonyl)-4-oxocyclohexa-2,5-dienylidene]methylene}bis(2-methoxybenzoate) [2] was prepared by reaction of 5,5'-[(3-carboxy-4-oxocyclohexa-2,5-dienylidene)methylene]bis(2-hydroxybenzoic acid) [1] with dimethyl sulphate in presence of anhydrous sodium carbonate in dry acetone. The trihydrazide derivative [3] was obtained from treatment of triester derivative [2] with hydrazine monohydrate in absolute ethanol. Reaction of the trihydrazide derivative [3] with each Furfural and Salicyladehyde, respectively, in presence of glacial acetic acid as catalyst in absolute ethanol resulted the formation of new triimine derivatives [4] and [5], respectively. Treatment of the resulting imines [4] and [5] with each maleic anhydride, phthalic anhydride and 3-nitrophthalic anhydride, respectively, under cycloaddition reactions conditions produced new tri(1,3-oxazepine) derivatives [6-8] and [9-11] respectively. These new imines and 1,3-oxazepine derivatives may be used as antibiotics.The structures of all prepared compounds were confirmed by C. H. N. elementary analysis and FT-IR spectra.