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. 2018 Jul 30;8(48):27131-27143.
doi: 10.1039/c8ra05690k.

An efficient and ecofriendly synthesis of highly functionalized pyridones via a one-pot three-component reaction

Hajar Hosseini  1 , Mohammad Bayat  1
Affiliations

An efficient and ecofriendly synthesis of highly functionalized pyridones via a one-pot three-component reaction

Hajar Hosseini et al. RSC Adv. .

Abstract

A simple and convenient protocol has been developed for the synthesis of N-amino-3-cyano-2-pyridone derivatives by a one-pot reaction of cyanoacetohydrazide, activated nitrile substrates (malononitrile, ethyl cyanoacetate, cyanoacetamide) and aromatic aldehydes in the presence of piperidine in water or a mixture of water and ethanol. The sequence of cascade reactions includes Knoevenagel condensation, Michael addition, intramolecular cyclization, imine-enamine tautomerization and oxidative aromatization. The main advantages of this procedure are availability of starting compounds, simple procedure, mild conditions, easy purification of products and the use of water or water/ethanol as green solvents.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Biodynamic activities of different derivatives of 3-cyano-2-pyridone.
Scheme 2
Scheme 2. Summary of previous studies of 3-cyano-2-pyridones synthesis.
Scheme 3
Scheme 3. Synthetic scheme for generation of products 4, 5, 6.
Fig. 1
Fig. 1. The 1H and 13C NMR spectrums of 4a.
Fig. 2
Fig. 2. The 1H and 13C NMR spectrums of 5a.
Fig. 3
Fig. 3. The 1H and 13C NMR spectrums of 6a.
Scheme 4
Scheme 4. Proposed mechanism for the formation of products 4, 5, 6.
See this image and copyright information in PMC

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