Synthesis and characterization of novel 1,3-oxazepin-5(1H)-one derivatives via reaction of imine compounds with isobenzofuran-1(3H)-one

Abstract

The objective of this work is preparation of imine compounds from aromatic al dehyde reaction with aromatic primary amines to interfere with the preparation of disubstituted-oxazepine derivatives from the reaction of prepared imine com pounds with isobenzofuran-1(3H)-one compound. Experimental part included synthesis of imine compounds (S1 -S5 ) and synthesis of disubstituted-oxazepine derivatives (S6 -S10). A number of new disubstituted-oxazepine derivatives were synthesized by acid-catalyzed cycloaddition- reaction of imine compounds with isobenzofuran-1(3H)-one in anhydrous THF under dry and reflux conditions with high yields. Imine compounds were synthesized by thermal condensation reaction of aromatic aldehydes, with aromatic primary amines. The products were identi fied by their melting point, FT-IR and 1H-NMR spectra. The formation of stable 7th – membered 1,3- oxazepine ring has been achieved by (5+2) cycloaddition re action of isobenzofuran-1(3H)-one compound and imine group. The results of FT IR and 1H-NMR showed that the target molecules were clearly formed due to the least obstructive effect in all preparation processes