A three component one-pot synthesis of N-amino-2-pyridone derivatives catalyzed by KF-Al₂O₃

Abstract

Synthesis of 1,6-diamino-4-phenyl-3,5-dicyano-2-pyridone derivatives via a one-pot, three-component reaction of aryl aldehydes, malononitrile, and cyanoacetic hydrazide at room temperature using KF-Al₂O₃ as a recyclable catalyst have been developed. The reaction proceeds through the initial Knoevenagel condensation between aldehyde and malononitrile in the presence of KF-Al₂O₃ to form the benzylidene derivative which then undergoes Michael addition with cyanoacetic hydrazide followed by intramolecular cyclization of the resulting intermediate to produce the N-amino-2-pyridones in good to excellent yields. The structure of the synthesized compounds were characterized and established on the basis of their spectral data analysis and single-crystal XRD analysis.

Graphical Abstract

Keywords:

• KF-Al₂O₃
• multi-component reactions
• N-amino-2-pyridones

Acknowledgments

The authors thank the UGC for financial support through research fellowship and DST-PURSE for the XRD facility. The authors also acknowledge the support of SAIF-NEHU, Shillong, SAIF-CDRI, Lucknow and the Department of Chemistry-NEHU for providing the analytical support.