Introducing rGO@Fe<sub>3</sub>O<sub>4</sub>@Ni as an efficient magnetic nanocatalyst for the synthesis of tetrahydrobenzopyranes via multicomponent coupling reactions of dimedone, malononitrile, and aromatic aldehydes

An easy, effective and eco‐friendly one‐pot process for the preparation of 4H‐pyran compounds has been established by using a catalytic amount of reduced graphene oxide functionalized with diethylenetriamine (rGO‐DETA) in water under mild conditions. The functionalized catalyst was very effective for this one‐pot reaction and provided the desired products 1a–t with good to high yields (87%–97%) in short reaction times. Moreover, rGO‐DETA composite could be reused for four cycles without an obvious decrease in its performance. In the next step, two pyran derivatives 1f and 1h were used to synthesize the corresponding pyran‐like tacrine derivatives 3f and 3h via the reaction of cyclohexanone, aluminum trichloride in reflux of 1,2‐dichloroethane as solvent. Antibacterial activity of several of the prepared compounds was assessed against Gram‐positive and Gram‐negative bacteria by well and disk diffusion techniques. The 4H‐pyran 1g and 1s (2000 μg/ml) were effective against Micrococcus luteus as a Gram‐positive bacterium by recording a zone of inhibition of 15 and 16 mm, respectively. 4H‐pyran 1m showed moderate antibacterial behavior against both M. luteus and Serratia marcescens. Pyran‐like tacrine analog 3f (50 mg/ml) displayed antibacterial behavior towards Staphylococcus aureus as Gram‐positive and S. marcescens as Gram‐negative bacteria with zones of inhibition of 13 and 12 mm, respectively. 4H‐pyran 1j featured a minimum inhibitory concentration value of 39.06 μg/ml for M. luteus, which is the closest value to ampicillin.

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Functionalized reduced graphene oxide as a useful and efficient base catalyst for the preparation of 4H‐pyran and pyran‐like tacrine compounds and their antibacterial activity

Mirza‐Aghayan

Mohammadi

Boukherroub

et al. 2022

Journal of Heterocyclic Chem

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The Immobilized Zirconocene Chloride on Magnetite‐reduced Graphene Oxide: A Highly Efficient and Reusable Heterogeneous Nanocatalyst for One‐pot Three‐component Synthesis of Tetrahydrobenzo[b]pyrans and Dihydropyrano[3,2‐c]chromenes

Bayzidi

Zeynizadeh

2022

ChemistrySelect

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The present paper describes the synthesis and characterization of the functionalized magnetite reduced graphene oxide (rGO@Fe3O4) with zirconocene dichloride as rGO@Fe3O4@ZrCp2Cl2. The prepared magnetic nanomaterial was characterized by Fourier‐transform infrared spectroscopy (FT‐IR), scanning electron microscopy (SEM), energy‐dispersive X‐ray spectroscopy (EDX), X‐ray diffraction (XRD), thermogravimetric analysis (TGA), vibrating sample magnetometer (VSM), inductively coupled plasma optical emission spectroscopy (ICP‐OES) and mass spectrometry (MS). This new heterogeneous nanocatalyst showed the perfect catalytic activity towards synthesis of tetrahydrobenzo[b]pyran and Dihydropyrano[3,2‐c]chromenes derivatives through multicomponent reaction of dimedone or 4‐hydroxycoumarin, malononitrile and aromatic aldehydes in polyethylene glycol 400 (PEG‐400) at 100 °C. The influence of the amount of nanocatalyst, varying temperature of the reaction and the kind of solvent on the rate of condensation reaction was investigated. Recovery and reusability of the applied nanocatalyst was examined for five consecutive cycles without the significant loss of its catalytic activity.

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p‐Toluene Sulphonic Acid (PTSA): An Efficient Catalyst for One‐Pot Three‐Component Synthesis of Novel 3‐Pyrazolyl‐Thiazolidin‐4‐One Derivatives

Das,

Paul,

Mitra

et al. 2024

ChemistrySelect

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This research article focuses on the pathway for metal‐free unprecedented one‐pot three‐component synthesis of biologically active 3‐pyrazolyl‐thiazolidin‐4‐one derivatives through cyclo‐condensation of aromatic aldehydes, 1H‐pyrazol‐3‐amine and thioglycolic acid in aqueous medium. p‐Toluene sulphonic acid (PTSA), a non‐toxic, cheaper, easily accessible, eco‐benign, organic acid‐catalyst was explored to mediate this reaction. Formation of novel 3‐pyrazolyl‐thiazolidin‐4‐one derivatives, environment‐benign conditions, quick reaction time, excellent functional group acceptance and moderate to high yield of the products are some of the chief advantages of the reaction. Further, this methodology will surely contribute in various fields of synthetic organic methodology, pharmaceutical industry and natural bio‐active product synthesis.

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Introducing rGO@Fe₃O₄@Ni as an efficient magnetic nanocatalyst for the synthesis of tetrahydrobenzopyranes via multicomponent coupling reactions of dimedone, malononitrile, and aromatic aldehydes

Cited by 12 publications

References 90 publications

Functionalized reduced graphene oxide as a useful and efficient base catalyst for the preparation of 4H‐pyran and pyran‐like tacrine compounds and their antibacterial activity

Functionalized reduced graphene oxide as a useful and efficient base catalyst for the preparation of 4H‐pyran and pyran‐like tacrine compounds and their antibacterial activity

The Immobilized Zirconocene Chloride on Magnetite‐reduced Graphene Oxide: A Highly Efficient and Reusable Heterogeneous Nanocatalyst for One‐pot Three‐component Synthesis of Tetrahydrobenzo[b]pyrans and Dihydropyrano[3,2‐c]chromenes

p‐Toluene Sulphonic Acid (PTSA): An Efficient Catalyst for One‐Pot Three‐Component Synthesis of Novel 3‐Pyrazolyl‐Thiazolidin‐4‐One Derivatives

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Introducing rGO@Fe3O4@Ni as an efficient magnetic nanocatalyst for the synthesis of tetrahydrobenzopyranes via multicomponent coupling reactions of dimedone, malononitrile, and aromatic aldehydes

Cited by 12 publications

References 90 publications

Functionalized reduced graphene oxide as a useful and efficient base catalyst for the preparation of 4H‐pyran and pyran‐like tacrine compounds and their antibacterial activity

Functionalized reduced graphene oxide as a useful and efficient base catalyst for the preparation of 4H‐pyran and pyran‐like tacrine compounds and their antibacterial activity

The Immobilized Zirconocene Chloride on Magnetite‐reduced Graphene Oxide: A Highly Efficient and Reusable Heterogeneous Nanocatalyst for One‐pot Three‐component Synthesis of Tetrahydrobenzo[b]pyrans and Dihydropyrano[3,2‐c]chromenes

p‐Toluene Sulphonic Acid (PTSA): An Efficient Catalyst for One‐Pot Three‐Component Synthesis of Novel 3‐Pyrazolyl‐Thiazolidin‐4‐One Derivatives

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Introducing rGO@Fe₃O₄@Ni as an efficient magnetic nanocatalyst for the synthesis of tetrahydrobenzopyranes via multicomponent coupling reactions of dimedone, malononitrile, and aromatic aldehydes