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ACTA Pharmaceutica Sciencia
2017 , Vol 55 , Num 4
Synthesis and Characterization of Novel 1,3-oxazepin-5(1H)-one Derivatives via Reaction of Imine Compounds with Isobenzofuran-1(3H)-one
1 Department of Scientific Affairs and Graduate Studies, University of Fallujah, Anbar, Iraq2 Department of Chemistry, College of Education for Pure Sciences, University of Anbar, Al-Anbar, Iraq
3 Department of Ecology, College of Applied Sciences-Heet, University of Anbar, Al-Anbar, Iraq
DOI : 10.23893/1307-2080.APS.05525 Viewed : 19558 - Downloaded : 8684 The objective of this work is preparation of imine compounds from aromatic aldehyde reaction with aromatic primary amines to interfere with the preparation of disubstituted-oxazepine derivatives from the reaction of prepared imine compounds 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 identified 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 reaction of isobenzofuran-1(3H)-one compound and imine group. The results of FTIR and 1H-NMR showed that the target molecules were clearly formed due to the least obstructive effect in all preparation processes. Keywords : Imine compound; isobenzofuran-1(3H)-one; disubstituted-oxazepine derivatives