Synthesis, characterization and kinetic studies of ethylene-[1,3] oxazinan - 4,6- dione, carbonyl-[1,3] oxazinan-4,6- dione from reaction of schiff-bases of ethylene diamine, urea and thiourea with malonic anhydride

Abstract EN

N-benzylidene2-({2-[(2-hydroxy-benzylidene)-amino]-ethylimino}-methyl)- phenol,1,3-Bis-(2-hydroxy-benzylidene)-urea and1,3-Bis-(2-hydroxy-benzylidene)- Thiourea (Schiff bases) were prepared by condensation of Ethylene diamine,urea and thiourea with Salicylaldehyde and 4-dimethyl amine benzaldhyde.

These Schiff bases were reacted with Malonic anhydride by refluxing it in absolute ethanol at 78°C for 1,3 and 2 hrs.

respectively to give a six-membered heterocyclic ring system; 2-(2-hydroxy-phenyl)-3-{2-[2-(2-hydroxyphenyl)- 4,6-dioxo-[1,3]oxazinan-3-yl]-ethyl}-[1,3]oxazinan-4,6-dione,2-(2-hydroxyphenyl)- 3-[2-hydroxy-phenyl)-4,6-dioxo-[1,3]oxazinan-3-carbonyl]-[1,3]oxazinan- 4,6-dione and 2-(2-hydroxy-phenyl)-3-[2-hydroxy-phenyl)-4,6-dioxo-[1,3]oxazinan- 3-thiocarbonyl]-[1,3]oxazinan-4,6-dione.

The costants of reaction velocity for the compounds (Schiff-bases) with (malonic anhydride) were studied and showed that the reaction was a first-order one.

Some of the 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.