Paper
Facile synthesis and antimicrobial activity of pyrazol-4-yl- and 2H-chromene-based substituted anilines via Michael addition followed by aromatization
Published Oct 20, 2022 · Venkateswarlu Banoji, Kishore Kumar Angajala, Koteshwar Rao Ravulapelly
Synthetic Communications
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Abstract
Abstract Herein, we report a facile one-pot synthetic method for a new class of pyrazol-4-yl- and 2H-chromene-based substituted anilines (arenes) from ethyl 2-cyanoacetate, pyrazole aldehydes, and various nitrostyrenes in the presence of the catalyst Et3N (5 mol%) in ethanol under reflux conditions. This method requires a common organocatalyst, inexpensive starting materials, and short reaction times. A wide range of substrate scaffolds were tolerated well to afford the desired products in good to excellent yields (85–95%). Two compounds of pyrazolyl based anilines bearing the electron donating methoxy groups exhibited emissions in the redshift region and could have potential applications as fluorescence probes in biological imaging. Seven compounds of pyrazolyl based anilines bearing the electron donating methoxy and methyl groups demonstrated significant antibacterial and antifungal activity against the tested microbial strains and dermatophyte fungi, respectively. Graphical Abstract
This study presents a facile one-pot method for synthesizing pyrazol-4-yl- and 2H-chromene-based substituted anilines, with potential applications in biological imaging and antibacterial and antifungal activity.
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