Synthesis, characterization and Density Functional Theory study of some new Benzotriazole derivatives

In this research some 1,3-oxazepine and 1,3-diazepine derivatives were prepared through a two-step process:- first step benzotriazole was converted to [1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-chloroethanone] [A] by the reaction betweenbenzotriazole with chloroacetyl chloride in the presence of triethylamine in DMF, Then the conversion of[A] to 1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-hydrazinylethanone] [B] by reaction with hydrazine in absoluteethanol. Schiff bases [C1-C5] were synthesized by the condensation of different aromatic aldehydes such as [p-dimethylaminobenzaldehyde , 4-chlorobenzaldehyde ,4-nitrobenzaldehyde,4-hydroxybenzaldehyde,4-hydroxy-3-methoxy benzaldehyde]with [B]in the presence of glacial acetic acid as catalyst in absolute ethanol, Then the resulting imines derivatives [C1-C5] were reacted with maleic anhydride and phathalic anhydride in dry benzene to give new 1,3-oxazepine-4,7-dione ring derivatives [D1-D5] and [D6-D10]respectively. The last prepared compounds were reacted with Benzidineto give 1, 3-diazepine-4, 7-dione derivatives [F1-F10].All prepared compounds were characterized by melting points and FT-IR spectroscopy, some of them were characterized by 1H-NMR andC.H.N analysis.The molecular geometry, bond lengths, bond angles and energies of the new compound have been investigated by Density Functional Theory (DFT) using B3LYP functional with 6-31G (d, P) basis sets. The frontier molecular orbital (FMO) analysis were considered by theoretical calculations using B3LYP 6-311G (d, P) level.