Abstract
Herein, we describe a one-pot synthesis of some novel 2-(3-alkyl/aryl-5-trifluoromethylpyrazol-1-yl)-4-(coumarin-3-yl)thiazoles (6) involving the reaction of 3-alkyl/aryl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazole-1-thiocarboxamides (3) with 3-bromoacetylcoumarins (5) in the presence of sodium carbonate in ethanol. Reaction of 3 with 5 in the absence of sodium carbonate, however, resulted in the formation of 2-(3-alkyl/aryl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles, which were subsequently dehydrated to 6 by refluxing in ethanol in the presence of sodium carbonate. The structure of the synthesized compounds (6) was confirmed by infrared (IR), mass, 1H NMR, and 13C NMR spectra and elemental analysis data. Newly synthesized compounds (6) showed moderate to good activity against Gram-positive bacteria.
GRAPHICAL ABSTRACT
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ACKNOWLEDGMENTS
Thanks are due to Sophisticated Analytical Instrument Facility (SAIF), Central Drug Research Institute (CDRI), Lucknow; SAIF, Panjab University, Chandigarh, India; and University of California San Francisco (UCSF), USA, for providing 19F NMR, elemental analyses, and HRMS spectra, respectively.
SUPPLEMENTAL MATERIAL
Supplemental data for this article can be accessed on the publisher’s website.