Synthesis of Novel 1, 3 -Oxazepine Compounds from New Azo Schiff bases Containing Thiadiazole Moiety

Abstract

In this work new Azo imines [3-4] and 1,3-oxazepine derivatives [5-10] were prepared starting from azoaldehyde derivative 2-Hydroxy-5-(5-thiole-[1,3,4] -thiadiazol-2-ylazo)-benzaldehyde [2]. Azoaldehyde derivative [2] was prepared via coupling reaction between phenoxide anion of o-Hydroxy benzaldehyde [1] and 5-thiole-1,3,4-thiadiazol-2-yl diazonium chloride.The new imines [3] and [4] were prepared by reaction of azoaldehyde derivative [2] with each primary amines 2-Amine-1,3,4-thiadiazole -5- thiol and 5-(Benzylthio)-1,3,4-thiadiazole-2- amine in presence of glacial acetic acid as catalyst in absolute ethanol , respectively. The new 1,3-oxazepine derivatives [5-10] were obtained from treatment of each new Schiff bases derivatives [4] and [5] with each maleic anhydride , phthalic anhydride and 3-Nitrophthalic anhydride ,respectively , in dry benzene.These new prepared compounds might have some biological activity. All new derivatives were characterized by (C.H.N.) elementary analysis and FT-IR spectra.