Synthesis and Characterization of (Diazenyl, Chalcone, Pyrazole)-Derivatives

In this study, heterocyclic compounds such as (isoxazolederivatives, pyrazol derivatives, oxazepinederivatives), were prepared by reaction2-aminobenzaldehyde with salicylaldehyde to get azo compound (5-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-hydroxybenzaldehyde) (1), which react (in acid medium ) with 4-Bromoaniline to get 4-((1Hbenzo[ d]imidazol-2-yl)diazenyl)-2-(((4-bromophenyl)imino)methyl)phenol(2), and react with 4-aminobenzoicacid to get 1-(4-((5-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-hydroxybenzylidene)amino)phenyl)ethanone(3) (both shiff base). in other side, (1) react (in base medium) with 4-Bromoacetophenon to get 3-(5-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-hydroxyphenyl)-1-(4-bromophenyl)prop-2-en-1-one(4), and react with 4-hydroxyacetophenone to get 3-(5-((1Hbenzo[d]imidazol-2-yl)diazenyl)-2-hydroxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one(5) (both chalcone derivatives).(2) and (3)react with phthalic anhydride and maliec anhydride to get 3-(5-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-hydroxyphenyl)-4-(4-bromophenyl)-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione(6),3-(5-((1Hbenzo[d]imidazol-2-yl)diazenyl)-2-hydroxyphenyl)-4-(4-acetylphenyl)-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione(7), 2-(5-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-hydroxyphenyl)-3-(4-bromophenyl)-2,3-dihydro-1,3-oxazepine-4,7-dione(8), 2-(5-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-hydroxyphenyl)-3-(4-acetylphenyl)-2,3-dihydro-1,3-oxazepine-4,7-dione(9). (oxazepine derivatives) (4) and (5) react with hydrazinhydrate to get 4-((1Hbenzo[ d]imidazol-2-yl)diazenyl)-2-(3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-5-yl)phenol(10), 4-((1Hbenzo[ d]imidazol-2-yl)diazenyl)-2-(3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-5-yl)phenol(11), and react with phenylhydrazine to get 4-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-(5-(4-bromophenyl)-1-phenyl-2,3-dihydro-1Hpyrazol-3-yl)phenol(12), 4-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-(5-(4-hydroxy phenyl)-1-phenyl-2,3-dihydro-1Hpyrazol-3-yl)phenol(13) (pyrazol derivatives). 4 and 5 react with hydroxylaminehydrochlorideto get 4-((1Hbenzo[ d]imidazol-2-yl)diazenyl)-2-(3-(4-bromophenyl)-2,5-dihydroisoxazol-5-yl)phenol(14), 4-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-(3-(4-hydroxyphenyl)-2,5-dihydroisoxazol-5-yl)phenol(15 (isoxazolederivatives). All this compounds characterized by means of FT-IR, and some of the compounds by means ¹H-NMR,and 13C-NMR and follow reaction by R_f-TLC and Measurement melting point.