Synthesis of New Imidazole Derivatives

In this work 4-(4-hydroxyphenyl)- 2-methyl-oxazol-5-(4H)-one(1) was synthesized from reaction of amino acid [2-amino-2-(4-hydroxy phenyl) acetic acid] with acetic anhydride and then was converted into the 1-amino-4-(4-hydroxyphenyl)-2-methyl-1H--imidazole-5(4H)-one (2) by reaction with hydrazine hydrate. Ester derivative (3) was synthesized from reaction of ethyl bromoacetate with compound (2), compound (3)was treated with hydrazine to give acetoyl hydrazide derivative (4). Azomethines (8-12)) were synthesized from the corresponding aromatic aldehyde and the acetoyl hydrazide derivative (4). On the other hand treatment of compound (4) with (CS2/KOH) gave oxadiazole derivative (5). Compound (6) 3-thiourea-5-(4- hydroxyphenyl)-2-methyl-3,5-dihydro-(4H)-imidazole-4-one was synthesized from the reaction of compound (1) with thiosemicarbazide than with diethylmalonate gave thiobarbituric acid derivative (7). Compounds (13-20) were synthesized from the reaction of compound (2) with aromatic aldehydes.Reaction of compounds (13-20) with 3,5- dinitrobenzoylchloride leads to addition reaction of double bond azomethine group give (21-28) derivatives, which upon refluxing with thiourea in absolute ethanol yield 1-[(2,5-dinitrobenzoyl)[2-methyl-5-(4- hydroxyphenyl)-4-oxo-imidazol-3-(4H)-yl] amino (aryl) methyl imidothiocarbamate derivatives (29-36). The synthesized compounds were confirmed by their IR and UV. Visible Spectra.