Fe3O4@SiO2‐imid‐PMAn Magnetic Porous Nanosphere as Reusable Catalyst for Synthesis of Polysubstituted Quinolines under Solvent‐free Conditions

Esmaeilpour, Mohsen; Javidi, Jaber

doi:10.1002/jccs.201400380

Cited by 29 publications

(7 citation statements)

References 49 publications

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“…77, 146.29, 141.83, 135.96, 134.61, 131.24, 130.30, 129.09 (2×), 128.92, 128.65 (2×), 128.22, 126.96, 124.43, 35.05, 30.30, 23.36. -9-phenyl-1,2,3,4-tetrahydroacridine (6d) 41 Yield: 275 mg (94%); colorless crystals; mp 172-173 °C (Lit. 41 163-165 °C).…”

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confidence: 99%

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Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones

Chan¹,

Lai²,

Wang³

2020

Synthesis

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An efficient and eco-friendly synthetic route for Friedländer quinoline synthesis of polysubstituted quinolines is described. This green chemical method starts from various 2-aminobenzophenones and mono- or dicarbonyl synthons and uses reusable Nafion NR50 material as a solid catalyst in ethanol under microwave irradiation. The protocol has a high generality of functional groups and provides the desired quinolines in good to excellent yields. Some structures were confirmed by single-crystal X-ray diffraction analysis.

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confidence: 99%

“…-9-phenyl-1,2,3,4-tetrahydroacridine (6d) 41 Yield: 275 mg (94%); colorless crystals; mp 172-173 °C (Lit. 41 163-165 °C).…”

mentioning

confidence: 99%

Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones

Chan¹,

Lai²,

Wang³

2020

Synthesis

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“…Magnetic Fe 3 O 4 particles were synthesized based on a modified co‐precipitation method . Briefly, the mixture of FeCl 3 .6H 2 O (1.3 g, 4.8 mmol), FeCl 2 .4H 2 O (0.9 g, 4.5 mmol) and polyvinyl alcohol (PVA 15000) (1 g) as a surfactant was dissolved in water (30 ml) with vigorous stirring.…”

Section: Methodsmentioning

confidence: 99%

Palladium nanoparticles immobilized on EDTA‐modified Fe₃O₄@SiO₂ nanospheres as an efficient and magnetically separable catalyst for Suzuki and Sonogashira cross‐coupling reactions

Esmaeilpour

Zahmatkesh

Fahimi

et al. 2018

Applied Organom Chemis

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In this study, a novel heterogeneous palladium catalyst was synthesized by anchoring palladium onto ethylenediaminetetraacetic acid (EDTA)‐coated Fe3O4@SiO2 magnetic nanocomposite and used for the Suzuki and Sonogashira cross‐coupling reactions. The properties of the magnetic catalyst were characterized by FT‐IR, XRD, TEM, FE‐SEM, DLS EDX, XPS, N2 adsorption‐desorption isotherm analysis, TGA, VSM, elemental analysis and the loading level of Pd in catalyst was measured to be 0.51 mmol/g by ICP. The catalyst was used in Suzuki cross‐coupling reactions of various aryl halides, including less reactive chlorobenzenes with phenylboronic acid without any additive or ligand under green conditions. Furthermore, we have reported this recyclable catalytic system for Sonogashira cross‐coupling reactions of various aryl halides (I, Br, Cl) under copper and ligand‐free conditions in the presence of DMF/H2O (1:2/v:v) as a solvent. The magnetic catalyst could also be separated by an external magnet and reused six times without any significant loss of activity.

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“…Several methods must be highlighted for the Friedländer synthesis of quinolones under conventional conditions, all regarding the use of heterogeneous and recyclable catalysts. Fe 3 O 4 @SiO 2 -imid-PMA n , Ni NPs, sulfamic acid and nanoflake ZnO catalysts have all presented great yields in solvent-free conditions for a great variety of substituents. Moreover, the first three methods were performed in short reaction times (under 1 h) and required only 5%–10% mol of catalyst to reach full catalytic activity.…”

Section: Nonenergy Efficient Green Reactionsmentioning

confidence: 99%

Synthesis of Quinolines: A Green Perspective

Batista

Pinto

Silva

2016

ACS Sustainable Chem. Eng.

110

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The quinoline scaffold is present in a vast number of natural compounds and pharmacologically active substances, comprising a significant segment of the pharmaceutical market. The classical methods for the synthesis of this heterocyclic skeleton require the use of expensive starting materials and high temperature conditions. Chemists play a fundamental role in the construction of a sustainable future through the pursuit of greener chemical processes. As so, the development of new synthetic methods using more efficient energy sources and less hazardous solvents as well as renewable and eco-friendly catalysts to attain the quinoline scaffold can provide significant environmental and economic advantages. This review unveils green methods used in the synthesis of quinolones. Important green metrics are calculated for each proposed method and the statistical analysis allowed us to propose the best approaches for further investigation. The applied research is eventually unveiling the full potential of Friedländer and/or multicomponent reactions, to improve atom economy. The quinoline structural motif is readily available through a number of classical synthetic routes and from commercially available reagents. The Friedländer synthetic method (A) from ortho-aminoacetophenones (10) and the Skraup (B), Combes (D) and Doebner-Miller (F) syntheses from anilines (11), as well as its adaptations, are good examples. Moreover, the Conrad-Limpach (C), Gould-Jacobs (E) and Camps (G) routes for the synthesis of quinolones are widely used methods (Scheme 1). Still, all classical methods have similar disadvantages, requiring highly acidic and/or oxidizing media, high temperatures and long reaction times.Moreover, most of these synthetic routes present selectivity problems with meta-substituted substrates and its versatility is limited by the reactivity of the methylenic carbon involved in the aldol reaction. 19 Although efficient and versatile, classical routes towards the synthesis of quinolines present serious environmental concerns as most synthetic routes use great excess of a reagents and produce a significant amount of toxic waste.

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Fe₃O₄@SiO₂‐imid‐PMAⁿ Magnetic Porous Nanosphere as Reusable Catalyst for Synthesis of Polysubstituted Quinolines under Solvent‐free Conditions

Cited by 29 publications

References 49 publications

Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones

Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones

Palladium nanoparticles immobilized on EDTA‐modified Fe₃O₄@SiO₂ nanospheres as an efficient and magnetically separable catalyst for Suzuki and Sonogashira cross‐coupling reactions

Synthesis of Quinolines: A Green Perspective

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Fe3O4@SiO2‐imid‐PMAn Magnetic Porous Nanosphere as Reusable Catalyst for Synthesis of Polysubstituted Quinolines under Solvent‐free Conditions

Cited by 29 publications

References 49 publications

Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones

Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones

Palladium nanoparticles immobilized on EDTA‐modified Fe3O4@SiO2 nanospheres as an efficient and magnetically separable catalyst for Suzuki and Sonogashira cross‐coupling reactions

Synthesis of Quinolines: A Green Perspective

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Resources

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Fe₃O₄@SiO₂‐imid‐PMAⁿ Magnetic Porous Nanosphere as Reusable Catalyst for Synthesis of Polysubstituted Quinolines under Solvent‐free Conditions

Palladium nanoparticles immobilized on EDTA‐modified Fe₃O₄@SiO₂ nanospheres as an efficient and magnetically separable catalyst for Suzuki and Sonogashira cross‐coupling reactions