Synthesis of 2-unsubstituted imidazolones from bisamides via a one-pot,domino dehydration/base promoted cyclisation process

A one-pot, domino process was developed as an alternative approach for the preparation of 2-unsubstituted imidazolones. The methodology utilizes readily accessible bisamides, which upon a dehydration/cyclisation sequence produced imidazolones in good yields. The transformation relies on the compatibility of the dehydrating agent and base, and the reaction conditions tolerate various functional groups.     

Unexpected reductive transformation of 1-substituted 5-hydroxy-4,5-diphenyl-1H-imidazol-2(5H)-ones and their cyclic analogs by the reaction with thiourea and hydrochloric acid

An unexpected reductive transformation of 1-substituted 5-hydroxy-4,5-diphenyl-1H-imidazol-2(5H)-ones (imidazolones) and their cyclic analogs to give 1-substituted 4,5-diphenyl-1H-imidazol-2(5H)-ones (imidazolinones) upon reaction with thiourea and hydrochloric acid was discovered.     

Synthesis,antimicrobial and anti-inflammatory activities of some novel 5-substituted imidazolone analogs

In view of potent antimicrobial and anti-inflammatory activities exhibited by 5-substituted imidazolones, a variety of novel imidazolone analogs 3a-l were synthesized by the condensation of different substituted oxazolones 1 with various aromatic amines 2. All the synthesized compounds were screened for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Several analogs produced good or moderate activities particularly against the tested Gram-positive bacteria Micrococcus luteus and Gram-negative bacteria Pseudomonas aeruginosa and. Meanwhile, compounds 3b and 3c displayed marked antifungal activity against C. albicans. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenin-induced paw oedema method in rats. Two of 5-substituted imidazolone derivatives, 3k and 3d show good anti-inflammatory activity. The structures of all the newly synthesized compounds were elucidated using IR, ¹H NMR and ¹³C NMR.