Synthesis Some Novel 1,3-Thiazol-2-Amine Derivatives Containing Substituted Β-Lactam Ring and Study Their Antibacterial Activity

Abstract

This work describes the synthesis of a family of azoles containing β-lactam ring. The 2,5-dimethyl aniline was converted into diazonium salt, which were reacted with 2-aminothiazole under acidic condition to give azo-coupling compound 1. The product was subjected to the Schiff base reaction. Imine group was prepared by the reaction of azo compound with aldehydes (4-hydroxy-3-methoxybenzaldehyde, 2-hydroxy1-1naphthaldehyde, 4-hydroxy-3,5-dimethoxybenzaldehyde, 4-hydroxybenzaldehyde, 2-hydroxybenzaldehyde, 2-methylbenzaldehyde, 4-chlorobenzaldehyde, 4-methoxybenzaldehyde) under acidic condition to give the products 2-6. β-lactam ring was formed by the cycloaddition reaction of compounds contains imino group with chloroacetyl chloride under basic condition to give desired products 7-11 in good yields. The antibacterial tests were carried out using disk diffusion method and activities were good for some of these compounds.