Synthesis and Identification (Oxazepine, Pyrazole, Isoxazole) compounds from 2-Aminobenzimidazole

This research involved heterocyclic compounds such as (oxazepine derivatives, pyrazol derivatives, isoxazole derivatives), were prepared by reaction 2-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-((1H-benzo[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-((1H-benzo[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 malic 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-((1H-benzo[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-hydroxy phenyl) -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-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-(3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-5-yl)phenol (10), 4-((1H-benzo[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-1H-pyrazol-3-yl)phenol(12),4-((1H-benzo[d]imidazol-2-yl)diazenyl)-2-(5-(4-hydroxyphenyl)-1-phenyl-2,3-dihydro-1H-pyrazol-3-yl)phenol (13) (pyrazol derivatives).

4 and 5 react with hydroxylaminehydrochloride to get 4-((1H-benzo[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) (isoxazole derivatives). 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 Rf -TLC and Measure ment melting point.