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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 14
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Synthetic Communications Review

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

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Pages 1816-1827 | Received 19 Mar 2018, Published online: 18 Jun 2018
 

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

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.

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