A facile and efficient protocol for the synthesis of 2-amino-3-cyano-4H-pyran derivatives at ambient temperature

Polypyrrole (PPY)/Fe 3 O 4 /CNT has been synthesized and characterized by FT-IR, TEM and SEM techniques and its catalytic activity has been evaluated in the synthesis of several series of pyran derivatives. Tetrahydrobenzo[b]pyranes, 4Hpyran-3-carboxylates, 4H,5H-pyrano[3,2-c]chromenes and dihydropyrano[2,3-c] pyrazoles have been successfully prepared from one-pot three-component condensation of aldehyde, malononitrile and active methylene-containing compounds (dimedone /ethyl acetoacetate/4-hydroxycoumarin/3-methyl-2pyrazoline-5-one) using PPY/Fe 3 O 4 /CNT as a new and reusable heterogeneouscatalyst. The present method offer several advantages such as; high yields of products, short reaction times, easy work-up procedure and easy separation of the catalyst from the reaction mixture due to its magnetic character. Furthermore, chemoselective synthesis of bis-benzo[b]pyran from terephthalaldehyde can be achieved by this method.

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Polypyrrole/Fe₃O₄/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives

Hojati

Amiri

MoeiniEghbali

et al. 2018

Applied Organom Chemis

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Synthesis of hybrid perillyl‐4H‐pyrans. Cytotoxicity evaluation against hepatocellular carcinoma HepG2/C3A cell line

Paczkowski

Guedes

Mass

et al. 2020

Journal of Heterocyclic Chem

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A series of 15 new hybrid perillyl‐4H‐pyrans compounds was straightforwardly synthesized by a strategy combining the multicomponent reaction and the copper‐catalyzed alkyne‐azide cycloaddition (CuAAC). The 2‐amino‐4H‐pyrans‐3‐carbonitrile containing the alkyne moiety was prepared via multicomponent reaction between 1,3‐dicarbonyl, a propargyloxy aromatic aldehyde and malononitrile or ethyl α‐cyanoacetate. The alkyne derivative was sequentially reacted with the perillyl azide component through the copper‐catalyzed [3+2] Huisgen cycloaddition reaction. The antiproliferative activity of hybrid compounds were evaluated against the human hepatoma HepG2/C3A cell line.

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Synthesis and biological assessment of some fused Pyran derivatives

Shamili¹,

Kavitha²,

Srinivas³

et al. 2022

Journal of Heterocyclic Chem

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Pyran was formed by reacting methyl 3-methoxyacrylate (1) with 2-benzylidenemalanonitrile to form compound 2. The pyrano derivatives 3-6 were obtained by reacting the second molecule with 2-benzylidenemalanonitrile, carbon disulfide, formamide, and benzylidene cyclohexanone. Compound (2) interacted with ethyl chloroacetate to form compound 8, which then cyclized in the presence of sodium ethoxide to form compound 9. Compound 7 was formed when compound (2) was treated with acetic acid in the presence of sulfuric acid and reacted with ethylchloroacetate to form compound 10 and then was converted to compound 11 by the addition of sodium ethoxide. Analytical and spectral data have been used to determine the structures of the newly synthesized substances and they were then tested for their antibacterial and antioxidant activities. In terms of antioxidant activity, compounds 2 and 8 were found to have the greatest and lowest levels, respectively, against Enterobacter aerogenes.

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A facile and efficient protocol for the synthesis of 2-amino-3-cyano-4H-pyran derivatives at ambient temperature

Cited by 21 publications

References 16 publications

Polypyrrole/Fe₃O₄/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives

Polypyrrole/Fe₃O₄/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives

Synthesis of hybrid perillyl‐4H‐pyrans. Cytotoxicity evaluation against hepatocellular carcinoma HepG2/C3A cell line

Synthesis and biological assessment of some fused Pyran derivatives

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A facile and efficient protocol for the synthesis of 2-amino-3-cyano-4H-pyran derivatives at ambient temperature

Cited by 21 publications

References 16 publications

Polypyrrole/Fe3O4/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives

Polypyrrole/Fe3O4/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives

Synthesis of hybrid perillyl‐4H‐pyrans. Cytotoxicity evaluation against hepatocellular carcinoma HepG2/C3A cell line

Synthesis and biological assessment of some fused Pyran derivatives

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Product

Resources

About

Polypyrrole/Fe₃O₄/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives

Polypyrrole/Fe₃O₄/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives