An efficiently and quickly synthesized NiO@g-C3N4 nanocomposite-catalyzed green synthesis of spirooxindole derivatives

Moqadam, Zahra Amini; Allahresani, Ali; Hassani, Hassan

doi:10.1007/s11164-019-03951-9

Cited by 19 publications

(11 citation statements)

References 28 publications

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“…Furthermore, this catalyst could be recovered and reused up to 6 runs without loss of its catalytic efficiency. The great performance of this catalyst was probably achieved due to the homogenous distribution of the NiO NPs and their stabilization by the graphite carbon nitride nanosheets, which makes the NiO NPs more accessible on the surface of the material and therefore more available to catalyze the reaction [126] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

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Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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Section: Spirooxindole Derivativesmentioning

confidence: 99%

“…NiFe 2 O 4 NPs [12] , [57] SnO 2 NPs [74] ZrO 2 NPs [98] NiO‐SiO 2 [125] NiO@g‐C 3 N 4 [126] ZnO nanodiscs [127] SrFe 12 O 19 MNPs [154] Cell‐CuI NPs [187]…”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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“…A green methodology for the building up of derivatives of spirooxindoles 68, 63, 64 by applying another NiO based catalyst was designed by Moqadam et al 56 Here the catalyst was NiO@g-C 3 N 4 , in which nanosheets of graphitic carbon nitride was used to carry NiO nanoparticles, through which the catalytic activity was enhanced by decreasing the nanoparticle aggregation. The reaction between dicyanomethane 28, isatin 6 and 4-hydroxycoumarin 50 (or 1,3-diketoester 67 or cyclic 1,3-diketone 29) was catalyzed by 50 mg of NiO@g-C 3 N 4 in ethanol at 80 °C under reflux ( Scheme 27 ).…”

Section: Ni-catalyzed Spirooxindole Synthesismentioning

confidence: 99%

Transition metal-catalyzed synthesis of spirooxindoles

et al. 2021

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“…All the products are known compounds characterized by IR and NMR spectroscopy and CHN data for new compounds. Their melting points are compared with reported values [19][20][21].…”

Section: Preparation Of 1-benzyl-1h-123-triazolementioning

confidence: 99%

“…It has been found that spirooxindole derivatives exhibit diverse pharmaceutical and biological activities such as antimicrobial [15], antibiotic, anti-HIV [16], antimalarial, antitumor, anti-Alzheimer, and anti-tuberculosis agents [17]. Due to their importance, a number of procedures have been reported for the preparation of spirooxindole derivatives [18][19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Click approach to the novel 1,2,3-triazolium phosphotungstate organic–inorganic hybrids for the highly promoted synthesis of spirooxindoles

2021

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The synthesis and catalytic activity of three 1,2,3-triazole-based ionic organicinorganic hybrids as novel water-soluble catalysts for the efficient preparation of spirooxindole derivatives are described. At first, three different 1,2,3-triazoles were prepared by click reaction. Then, these synthesized compounds were reacted with 1,4-butane sultone to generate novel solid 1,2,3-triazolium-N-butyl sulfonate zwitterions. In the next step, the newly synthesized organic zwitterions were treated with an aqueous solution of phosphotungstic acid to give three novel 1,2,3-triazolium-N-butyl sulfonic acid phosphotungstates as targeted organic-inorganic hybrid catalysts. The prepared catalysts were fully characterized using FTIR, 1 H and 13 C NMR, XRD, elemental analysis (CHNS), ESI-MS, DSC, and TG techniques. The introduced novel SO 3 H-functionalized ionic hybrid catalysts have a cationic organic triazolium with phosphotungstate anion and are water-soluble with appropriate thermal stability. Their catalytic activity was explored for the synthesis of spirooxindoles via the three-component reaction of 1,3-dicarbonyl compounds, barbituric acid, and isatin derivatives. The synthesis of desired spirooxindole products was performed in acceptable times with excellent yields in the presence of low loading amount of the prepared 1,2,3-triazolium-N-butyl sulfonic acid phosphotungstate catalysts (10 mmol%) in water. Some highlighted superiorities of the introduced organic-inorganic hybrids in comparison with most of the previously reported catalysts are as follows: clean and straightforward preparation, novelty of the catalysts, green conditions, ease of recovery, and reusability up to three repeated runs with no significant decrease in the catalytic stability.

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An efficiently and quickly synthesized NiO@g-C3N4 nanocomposite-catalyzed green synthesis of spirooxindole derivatives

Cited by 19 publications

References 28 publications

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Transition metal-catalyzed synthesis of spirooxindoles

Click approach to the novel 1,2,3-triazolium phosphotungstate organic–inorganic hybrids for the highly promoted synthesis of spirooxindoles

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