Citric Acid/MCM‐48 Catalyzed Multicomponent Reaction: An Efficient Method for the Novel Synthesis of Quinoline Derivatives

Akpotu, Samson O.; Moodley, Brenda; Vamsi, Boddu; Ofomaja, Augustine E.; Maddila, Suresh; Jonnalagadda, Sreekantha B.

doi:10.1002/slct.201900907

Cited by 17 publications

(3 citation statements)

References 47 publications

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“…Adsorbent textural properties such as the pore diameter, volume, and surface significantly affect adsorption capacity. 41 It was observed ( Table 1 ) that an increase in GO-PEG concentration resulted in an increase in textural properties such as pore size/diameter, which will enhance the uptake of large pollutant molecules within the mesopores. Though the surface areas of the geomedia were slightly lowered, this was due to agglomeration of GO sheets attached on kaolin during the drying process.…”

Section: Resultsmentioning

confidence: 99%

Engineered Geomedia Kaolin Clay-Reduced Graphene Oxide–Polymer Composite for the Remediation of Olaquindox from Water

et al. 2022

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Globally, there is an upsurge in the use of unregulated veterinary pharmaceuticals with enhanced release into the environment, resulting in water pollution, which is difficult to remediate. To address this issue, we synthesized and characterized highly hydrophobic three-dimensional ordered engineered geomedia with multiple channels. Kaolin clay (K) was functionalized with either graphene oxide (GO) synthesized via Tour’s method or reduced GO in situ with covalently linked methoxyether polyethylene glycol (GO-PEG) using a simple and easily scalable amidation reaction. This was done to enhance the adsorption of olaquindox, a veterinary antibiotic. The X-ray diffraction profile confirmed the grafting of GO and GO-PEG to kaolin. Morphological analysis revealed the architecture of thin films of GO/GO-PEG grafted on the kaolin surface with extensive porosity. Energy-dispersive X-ray mapping, infra-red spectra, and elemental analysis confirmed the successful synthesis of the engineered geomedia composite of K, GO/rGO, and PEG (KrGO-PEG). Due to multiple surface functional groups of polyamide and amido-carbonic groups on the KrGO-PEG composite, it was suitable for olaquindox adsorption. In batch sorption studies of 0.5XKrO-PEG, the effect of pH (2–10) was negligible but with fast equilibrium time (2–1440 min) at 30 min, while the kinetics and equilibrium data suited the pseudo-second order and Langmuir models, respectively. The maximum adsorption value obtained for the composite was 59.5 mg/g; the higher the GO content, the higher the adsorption. The sorption mechanism was majorly through hydrophobic and π–π interactions. Regenerated/reused adsorbents after 4 cycles had the same efficacy in remediating olaquindox from simulated/real water.

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Section: Resultsmentioning

confidence: 99%

Engineered Geomedia Kaolin Clay-Reduced Graphene Oxide–Polymer Composite for the Remediation of Olaquindox from Water

et al. 2022

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“…This cagelike structure increases the energy barrier of nitrogen inversion so the lone pair is localized and makes DABCO more susceptible toward quaternization and ionic liquid preparation and further applied in organic reactions. − Regarding the abovementioned notable properties of 1,4-DHP derivatives, their synthetic methods have been investigated in various environmental conditions. − However, most of the research studies have been done on the synthesis of 3-carboxylate derivatives of 1,4,5,6,7,8-hexahydroquinoline compared to 3-carbonitrile derivatives. 1,4,5,6,7,8-Hexahydroquinoline-3-carbonitrile was previously synthesized using NH 4 OAc, sulfonated rice husk, nanosized MgO, nano-Fe 3 O 4 @TDI@TiO 2 , citric acid/MCM-48, and K 2 CO 3 catalyst. − Despite the undeniable advantages of these processes, some disadvantages are also present, like the involvement of metal catalysts, nonrecyclable catalysts, high catalyst loading, long reaction time, high temperature, and small substrate scope. Therefore, further efforts are needed to present more proficient and eco-benign methods for the synthesis of hexahydroquinoline-3-carbonitriles.…”

Section: Introductionmentioning

confidence: 99%

Tandem Protocol of Hexahydroquinoline Synthesis Using [H₂-DABCO][HSO₄]₂ Ionic Liquid as a Green Catalyst at Room Temperature

et al. 2023

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Green, eco-benign, and sustainable synthesis is paramount in present chemistry. Here, a facile, efficient, and [H 2 -DABCO][HSO 4 ] 2 ionic-liquid-catalyzed one-pot multicomponent synthesis of hexahydroquinolines was reported under ambient reaction conditions. The reaction of 1,3-dicarbonyls, malononitrile, and ammonium acetate with various aldehydes in the presence of an ionic liquid catalyst and EtOH solvent at room temperature afforded excellent yields (76−100%) of hexahydroquinolines under a short reaction time (5−15 min). Mild reaction conditions, broad substrate scope (28 derivatives), and column-chromatography-free synthesis with excellent catalytic efficiency and good recyclability rendered this protocol superior and practical. The greenness of the present method was assessed through eco-score and E-factor. The significant results in gram-scale synthetic conditions validate its applicability in industries as well as academia in the near future.

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“…Multi‐component reactions (MCRs) are vastly esteemed as synthetic approaches due to numerous components of variety can be presented into target molecule in a one‐pot reaction . MCRs are a greatly potent device in pharmaceutical, agro and combinatorial chemistry .…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Multicomponent Reaction: A Green and Catalyst‐Free Method for the Synthesis of Poly‐Functionalized 1,4‐Dihydropyridines

Maddila

Kerru

Chinnam³

et al. 2019

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A facile and an efficient procedure for the synthesis of poly‐substituted 1,4‐dihydropyridine derivatives under catalyst‐free conditions has been established by a one‐pot multi‐component reaction in EtOH solvent under microwave irradiation (150 W). The remarkable benefits of this approach are: simple operation, non‐toxic, short reaction time (< 5 min), excellent yields (93‐98%), no column chromatography, clean reaction profile and environmentally friendly reaction.

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Citric Acid/MCM‐48 Catalyzed Multicomponent Reaction: An Efficient Method for the Novel Synthesis of Quinoline Derivatives

Cited by 17 publications

References 47 publications

Engineered Geomedia Kaolin Clay-Reduced Graphene Oxide–Polymer Composite for the Remediation of Olaquindox from Water

Engineered Geomedia Kaolin Clay-Reduced Graphene Oxide–Polymer Composite for the Remediation of Olaquindox from Water

Tandem Protocol of Hexahydroquinoline Synthesis Using [H₂-DABCO][HSO₄]₂ Ionic Liquid as a Green Catalyst at Room Temperature

Microwave‐Assisted Multicomponent Reaction: A Green and Catalyst‐Free Method for the Synthesis of Poly‐Functionalized 1,4‐Dihydropyridines

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Citric Acid/MCM‐48 Catalyzed Multicomponent Reaction: An Efficient Method for the Novel Synthesis of Quinoline Derivatives

Cited by 17 publications

References 47 publications

Engineered Geomedia Kaolin Clay-Reduced Graphene Oxide–Polymer Composite for the Remediation of Olaquindox from Water

Engineered Geomedia Kaolin Clay-Reduced Graphene Oxide–Polymer Composite for the Remediation of Olaquindox from Water

Tandem Protocol of Hexahydroquinoline Synthesis Using [H2-DABCO][HSO4]2 Ionic Liquid as a Green Catalyst at Room Temperature

Microwave‐Assisted Multicomponent Reaction: A Green and Catalyst‐Free Method for the Synthesis of Poly‐Functionalized 1,4‐Dihydropyridines

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Tandem Protocol of Hexahydroquinoline Synthesis Using [H₂-DABCO][HSO₄]₂ Ionic Liquid as a Green Catalyst at Room Temperature