Abstract
A new series of N-thiazole, 3-phenyl, 4-substituted phenyl azetidine-2-ones 4(a-h) have been synthesized in good yields starting from 2-aminothiazole 1. In the first step, then Schiff's bases 3(a-h) are prepared by the condensation of 2-aminothiazole 1 with different aryl aldehydes 2(a-h). Finally, monocyclic -lactams, i.e. substituted azetidinones 4(a-h), were the products formed using three different methods by the dehydrative cyclocondensation of 3(a-h) with phenyl acetyl chloride in dioxane, phenyl acetic acid-thionyl chloride in dichloromethane and phenyl acetic acid-phosphorus oxychloride in dichloromethane in the presence of triethylamine. We found that latter method is the best as compared with the former two methods. The synthesized molecules 4(a-h) were screened for their antibacterial activity against four microorganisms: Staphylococcus aureus (Gram positive), Pseudomonas vulgaris (Gram positive), Pseudomonas aeruginosa (Gram negative), and Escherichia coli (Gram negative). Their antibacterial activities are reported, and on the basis of the screening data available, attempt is also made to elucidate the structure-activity relationship. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.