Novel, One-Pot, Three-Component, Regioselective Synthesis of Fluorine-Containing Thiazole and Bis-3H-thiazole Derivatives Using Polyvinyl Pyridine as Heterogeneous Catalyst, and Evaluation of Their Antibacterial Activity

Abstract

A convenient, one-pot, three-component regioselective synthesis of novel 2,2′-(1,4-phenylene)-bis-(3-aryl-2-substituted imino-4-aryl-3H-thiazole) derivatives from 1,4-phenylene diisothiocyanate, aryl amines, and various phenacyl bromide, and also the regioselective synthesis of 3-alkyl-2-(aryl imino)-4-cyclopropyl-5-(2′-fluorophenyl)-thiazole derivatives from alkylisothiocyanate, aryl amines, and 2-bromo-2-(2-fluorophenyl)-1-cyclopropylethanone in the presence of poly-4-vinyl pyridine as heterogenous basic catalyst are described. This efficient method produced the products at room temperature with excellent yields (82–96%). The structures of all products were characterized by spectral and elemental analyses. The antimicrobial activity of the synthesized compounds was evaluated against Salmonella enterica, Micrococcus luteus, Bacillus subtilis, and Pseudomonas aeruginosa.

GRAPHICAL ABSTRACT

Keywords:

• Antibacterial activity
• fluorine-containing thiazole
• heterogenous base catalysis
• one-pot
• 1,4-phenylene diisothiocyanate
• poly-4-vinyl pyridine
• three-component