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

Эффективный и экологичный синтез высокофункционализированных пиридонов посредством однореакторной трехкомпонентной реакции
Mohammad Bayat, Hajar Hosseini
2018-01-01

cascade reactionscyanoacetohydrazidegreen solventshighly functionalized pyridonesone-pot three-component reaction
-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.
1
A one-pot three-component reaction synthesizes highly functionalized 2-amino-3-cyano-2-pyridone derivatives from cyanoacetohydrazide, activated nitriles, and aromatic aldehydes.
2
Piperidine catalysis in water or water–ethanol enables the synthesis under mild, environmentally friendly conditions.
3
The cascade proceeds through Knoevenagel condensation, Michael addition, intramolecular cyclization, imine–enamine tautomerization, and oxidative aromatization.
4
The method accommodates malononitrile, ethyl cyanoacetate, and cyanoacetamide as activated nitrile substrates.
5
The procedure uses readily available starting materials and offers simple operation and product purification.

Highly functionalized 2-pyridone derivatives synthesized from cyanoacetohydrazide, activated nitriles, and aromatic aldehydes

The one-pot three-component cascade synthesis, reaction sequence, and ecofriendly mild-condition performance for producing highly functionalized 2-pyridones

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2018-01-01
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Mohammad Bayat
Hajar Hosseini
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