Synthesis of β-Amino Ketones using graphene oxide: a benign carbonaceous acid catalyst for Mannich reaction

Ganesan, Nagappan Saravana; Suresh, Palaniswamy

doi:10.1007/s11164-020-04324-3

Cited by 4 publications

(1 citation statement)

References 40 publications

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“…A plausible mechanism for this reaction is presented in Scheme 3. rGO-DETA surface comprises different groups such as hydroxyl, carboxyl, and amine groups, which confer acidic [47,48,67] and basic [68] characters to the material. Hydroxyl and carboxyl groups of rGO can activate the aldehyde and dimedone through interaction with the oxygen atom to increase the susceptibility of the aldehyde to nucleophilic attack and dimedone to produce the corresponding enolate, respectively.…”

Section: Catalytic Performance Of Rgo-deta Materialsmentioning

confidence: 99%

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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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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Section: Catalytic Performance Of Rgo-deta Materialsmentioning

confidence: 99%

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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An Efficient Synthesis of Heterogeneous and Hard Bound Ti^IV‐MCM‐41 Catalyzed Mannich Bases and π‐Conjugated Imines

Shenbagapushpam¹,

Muthukumar²,

Yuvaraj

et al. 2021

ChemistrySelect

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A heterogeneous and hard bound TiIV anchored MCM‐41 material has been successfully evaluated for catalytic applications in the one pot synthesis of highly functionalized β‐amino ketones and quinoline appended π‐conjugated imines via Mannich reaction and condensation reaction, respectively. The synthetic transformation was successfully catalyzed via the dual Bronsted and Lewis acetic nature of the Ti‐MCM‐41 material that provided excellent yields of the desired products. The heterogeneous catalyst shows good catalytic performance, facile separation from the reaction mixture and can be reused in more than five catalytic cycles without any significant loss in the yield.

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An Update on Graphene Oxide: Applications and Toxicity

et al. 2022

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Graphene oxide (GO) has attracted much attention in the past few years because of its interesting and promising electrical, thermal, mechanical, and structural properties. These properties can be altered, as GO can be readily functionalized. Brodie synthesized the GO in 1859 by reacting graphite with KClO 3 in the presence of fuming HNO 3 ; the reaction took 3−4 days to complete at 333 K. Since then, various schemes have been developed to reduce the reaction time, increase the yield, and minimize the release of toxic byproducts (NO 2 and N 2 O 4 ). The modified Hummers method has been widely accepted to produce GO in bulk. Due to its versatile characteristics, GO has a wide range of applications in different fields like tissue engineering, photocatalysis, catalysis, and biomedical applications. Its porous structure is considered appropriate for tissue and organ regeneration. Various branches of tissue engineering are being extensively explored, such as bone, neural, dentistry, cartilage, and skin tissue engineering. The band gap of GO can be easily tuned, and therefore it has a wide range of photocatalytic applications as well: the degradation of organic contaminants, hydrogen generation, and CO 2 reduction, etc. GO could be a potential nanocarrier in drug delivery systems, gene delivery, biological sensing, and antibacterial nanocomposites due to its large surface area and high density, as it is highly functionalized with oxygen-containing functional groups. GO or its composites are found to be toxic to various biological species and as also discussed in this review. It has been observed that superoxide dismutase (SOD) and reactive oxygen species (ROS) levels gradually increase over a period after GO is introduced in the biological systems. Hence, GO at specific concentrations is toxic for various species like earthworms, Chironomus riparius, Zebrafish, etc.

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Synthesis of β-Amino Ketones using graphene oxide: a benign carbonaceous acid catalyst for Mannich reaction

Cited by 4 publications

References 40 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

An Efficient Synthesis of Heterogeneous and Hard Bound Ti^IV‐MCM‐41 Catalyzed Mannich Bases and π‐Conjugated Imines

An Update on Graphene Oxide: Applications and Toxicity

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Synthesis of β-Amino Ketones using graphene oxide: a benign carbonaceous acid catalyst for Mannich reaction

Cited by 4 publications

References 40 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

An Efficient Synthesis of Heterogeneous and Hard Bound TiIV‐MCM‐41 Catalyzed Mannich Bases and π‐Conjugated Imines

An Update on Graphene Oxide: Applications and Toxicity

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An Efficient Synthesis of Heterogeneous and Hard Bound Ti^IV‐MCM‐41 Catalyzed Mannich Bases and π‐Conjugated Imines