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An efficient and mild method for the synthesis of 2-amino-4H-pyran-3-carbonitriles via coupling reaction of malononitrile and α,α’Bis(benzylidine) cyclohexanones in the presence of L-proline as a catalyst and acetonitrile as a solvent has been described. This method is a good option to obtain the title compounds in quantitative yields in shorter reaction times and in a simple way. The synthesized compounds were bio-evaluated for their possible antimicrobial activity against a panel of gram-positive and gram-negative bacterial strains and fungal strains by the known methods.