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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 Et 3 N (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.

synthetic communications

Facile synthesis and antimicrobial activity of pyrazol-4-yl- and  2H -chromene-based substituted anilines via Michael addition followed by aromatization