An efficient route for synthesis of 5,6-diphenylimidazo-[2,1-b]thiazoles as antibacterial agents

✍ Scribed by Zeinab A. Hozien; A. O. Sarhan Abd El-Wareth; Hassan A. H. El-Sherief; Abdalla M. Mahmoud

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2000
• Tongue: English
• Weight: 468 KB
• Volume: 37
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570370443

✦ Synopsis

Abstract

The reaction of 4,5‐diphenylimidazol‐2‐thione (1) with aromatic ketones 2a‐i using the acidified acetic acid method afforded the 4,5‐diphenyl(2‐imidazolylthio)acetophenones 3a‐h in good yields. While, the cyclized product 4i was obtained directly upon reaction of 1 with α‐acetyl naphthalene. Compounds 3a‐h were cyclized directly to the corresponding 3‐aryl‐5,6‐diphenylimidazo[2,1‐b]thiazoles (4a‐c) and (4e‐h). In the same manner the reaction of 1 with aliphatic and/or alicyclic ketones gave the 3‐(4,5‐diphenyl‐2‐imidazolylthio)acetone derivatives 5a‐d, 2‐(4,5‐diphenylimidazolylthio)cycloalkanones 8a,d and the tricyclic compounds 9b‐c respectively. The cyclized compounds 6a‐d and 9a,d were obtained by cyclization of 5a‐d and 8a,b respectively. Oxidation of 1 gives the corresponding bis(4,5‐diphenyl‐2‐imidazolyl)‐disulfide (10) in 90% yield. Some of the synthesized compounds were tested for antifungal and antibacterial activity.