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A new and suitable multicomponent one-pot reaction was developed for the synthesis of 2-amino-3-cyanopyridine derivatives. Background: This synthesis was demonstrated by the efficient and easy access to a variety of substituted 2-aminopyridines using enaminones as key precursors under solvent-free conditions. Methods: A range of spectroscopic techniques was used to determine and confirm the chemical structures (FTIR, ¹H NMR, ¹³C NMR). The antimicrobial potency of synthesized compounds (<b>2a</b>–<b>d</b>) was tested using disk diffusion assays, and the Minimum Inhibitory Concentration (MIC) for the active compounds was determined against a panel of microorganisms, including Gram-positive and Gram-negative bacteria and yeasts. Moreover, a docking analysis was conducted by Molecular Operating Environment (MOE) software to provide supplementary information about the potential, as well as an ADME-T prediction to describe the pharmacokinetic properties of the best compound and its toxicity. Results: The results of the antimicrobial activity indicated that compound <b>2c</b> showed the highest activity against Gram-positive bacteria, particularly <i>S. aureus</i> and <i>B. subtilis</i> whose MIC values were 0.039 ± 0.000 µg·mL⁻¹. The results of the theoretical study of compound <b>2c</b> were in line with the experimental data and exhibited excellent antibacterial potential. Conclusions: On the basis of the obtained results, compound <b>2c</b> can be used as an antibacterial agent model with high antibacterial potency.