Synthesis and biological evaluation of novel 2‐(4‐ O ‐β‐ D ‐glucosidoxyphenyl)‐4,5‐disubstituted imidazoles

Abstract magnified image A series of 2‐(4‐hydroxyphenyl)‐4,5‐disubstituted imidazoles (1a, 1b, 1c, 1d, 1e) prepared from α‐diketones, ammonium acetate, and p‐hydroxybenzaldehyde, which were glucosylated by using α‐acetobromoglucose to form 2‐(4‐O‐β‐D‐2,3,4,6‐tetra‐O‐acetyl‐glucosidoxyphenyl)‐4,5‐disubstituted imidazoles (2a, 2b, 2c, 2d, 2e) which on catalytic deacetylation with CH3ONa in methanol afforded the title compound 2‐(4‐O‐β‐D‐glucosidoxyphenyl)‐4,5‐disubstituted imidazoles (3a, 3b, 3c, 3d, 3e). Compounds were characterized by elemental analysis and by instrumental technique, similarly the title compounds were investigated for antimicrobial and antifungal activity. J. Heterocyclic Chem., (2010).