Synthesis, Characterization and Kinetic Studies of Some Oxazepine and Oxazepane Derivatives

Abstract

Bis(2-hydroxy-benzylidene)-Thiourea and 1,3-Bis-(dimethylaminobenzylidene)-Thiourea were prepared by condensation of Thiourea with one equivalent and two equivalent of substituted benzaldehyde. These Schiff-bases were reacted with one equivalent of Maleic , Succinic and Phthalic anhydride in absolute ethanol to give 7-membered heterocyclic ring system of 2-(2-Hydroxy-phenyl)-4,7dioxo-4,7-dihydro-[1,3] oxazpine-3-carbothioic acid amide and 2-(4-Dimethylaminophenyl)-4,7-dioxo-4,7-dihydro-[1,3]oxazepine-3-carbothioiacid amide, 1,3-Bis(2hydroxy-benzylidene)-Thiourea and 1,3-Bis-(dimethylamino-benzylidene)-Thiourea were reacted with two equivalent of Maleic and Succinic anhydride in same solvent to give 2 (7-membered) heterocyclic ring system of 2-(2-hydroxy-phenyl)-3-[2-(2hydroxy-phenyl)-4,7-dioxo-[1,3]oxazepine-3-carbothioyl]-2,3-dihydro-[1,3]oxazepine-a,7-dione and 2-(4-Dimethylamino-phenyl)-3-[2-(4-dimethylaminophenyl)-4,7-dioxo-[1,3]oxazepine-3-carbothioyl]-2,3-dihydro-[1,3]oxazepine-4,7dione. The constants of reaction velocity for (Schiff-bases)with Maleic , Succinic andPhthalic anhydride were studied and showed that the reaction wsa firstorder one .Some of thermodynamic characteristics were evaluated and showed differences among the prepared compounds . The final products were identified by their melting points, elemental analysis, IR, 1H NMR and UV-Visible spectra.