Synthesis of 1,4-disubstituted imidazole compounds with amino acids and determination of some biological activities

Amino acid esters 1 were reacted with formaldehyde in methanol and the in situ formed imines treated with phenacyl bromide oxime to give the corresponding 4-phenyl-2,5-dihydro-1H-imidazole-3-oxides 2. The 1,3-dipolar cycloaddition of the latter with dimethyl acethylenedicarboxylate provided the cycloadducts 3-4. The reflux of these compounds in acetonitrile in the presence of piperidine provided imidazoles 5 in high yields. The synthesized compounds were characterized spectroscopically and evaluated for in vitro antifungal activity against C.albicans fungus.