A facile and convenient green click synthesis has been developed for the preparation of new fluorinated 1,2,3-triazoles under solvent-free conditions via a Huisgen 1,3-dipolar cycloaddition reaction between dimethylacetylene dicarboxylate (DMADC) and fluorophenyl azides in excellent yields within 2 min. Treatment of the resulting diesters with hydrazine hydrate furnished the corresponding dihydrazides, which, upon condensation with benzaldehyde derivatives, afforded a new series of bis-hydrazones. All of the synthesized compounds were fully characterized using infrared (IR) spectroscopy, 1H, 13C and 19F nuclear magnetic resonance (NMR), mass spectrometry (MS) and elemental analysis. A preliminary bioassay indicated that some of the tested compounds exhibited significant antimicrobial activity.
Keywords:
free solvent reaction; click synthesis; 1,2,3-triazoles; Schiff bases; antimicrobial activity
