Zeolite enslaved transition metal complexes as novel heterogeneous catalysts for synthesis of polycyclic heterocycles using suzuki--miyaura cross coupling reaction under greener conditions

Sain, Shalu; Kishore, Dharma; Jain, Sonika; Sharma, Vivek; Srivastava, Manish; Sankararamakrishnan, Nalini; Mishra, Shruti; Dwivedi, Jaya; Wabaidur, Saikh Mohammad; Sharma, Swapnil

doi:10.1016/j.inoche.2020.108230

Cited by 18 publications

(6 citation statements)

References 24 publications

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“…In order to evaluate the antibacterial activity of the synthesized compounds, both Gram‐positive ( Staphylococcus aureus MTCC 6908 and Bacillus subtilis MTCC 1305) and Gram‐negative ( Escherichia coli MTCC 433 and Pseudomonas aeruginosa MTCC 2582) lyophilized bacterial strains were procured from MTCC (Microbial Type Culture Collection) Chandigarh, India. Later, bacterial strains were cultured and maintained in a nutrient broth medium [25] …”

Section: Methodsmentioning

confidence: 99%

“…Later, bacterial strains were cultured and maintained in a nutrient broth medium. [25] Determination of Half-Maximal Inhibitory Concentration (IC 50 )…”

Section: Antibacterial Activitymentioning

confidence: 99%

“…The general Suzuki-Miyaura catalytic cycle occurs through oxidative addition, transmetallation and reductive elimination. The reaction takes place by the catalytic species Pd(0) (25), generated in situ from palladium Pd(II) or directly from Pd(0) derivatives. Oxidative addition of the 4-iodo-1H-pyrazol-3-amine (12) furnishes the palladium complex [ArPdILn] (26).…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and Theoretical Studies of Biologically Active Thieno Nucleus Incorporated Tri and Tetracyclic Nitrogen Containing Heterocyclics Scaffolds via Suzuki Cross‐Coupling Reaction

Sain

Jaiswal

Jain

et al. 2022

Chemistry & Biodiversity

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A new series of thieno nucleus embellished trinuclear (19, 20) and tetranuclear (21–24) nitrogen heteroaryl have been synthesized by the Suzuki cross‐coupling reaction using bis(triphenylphosphine)palladium(II) dichloride. All the synthesized compounds were characterized by IR, 1H‐NMR, 13CNMR and Mass spectral properties. In vitro antibacterial studies of the synthesized compound were conducted using broth microdilution assay employing Gram‐positive and Gram‐negative strains and half‐maximal inhibitory concentration (IC50) was determined. The result showed that compound 20 possess best antibacterial activity against S. aureus and E. coli with IC50 values of 60 μg mL−1 and 90 μg mL−1. Further to determine the mode of antibacterial action, compounds 20 and 21 were examined for in vitro bacterial dehydrogenase inhibitory assay. To understand the binding affinity of the synthesized compounds, the docking study was performed in the bacterial dehydrogenase enzyme by AutoDock Vina software and structure was confirmed by Discovery Studio Visualizer. All the synthesized compounds were docked in a good manner within the active sites of the bacterial dehydrogenase enzyme and exhibited good binding energies.

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Section: Methodsmentioning

confidence: 99%

“…Later, bacterial strains were cultured and maintained in a nutrient broth medium. [25] Determination of Half-Maximal Inhibitory Concentration (IC 50 )…”

Section: Antibacterial Activitymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

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Synthesis and Theoretical Studies of Biologically Active Thieno Nucleus Incorporated Tri and Tetracyclic Nitrogen Containing Heterocyclics Scaffolds via Suzuki Cross‐Coupling Reaction

Sain

Jaiswal

Jain

et al. 2022

Chemistry & Biodiversity

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“…Many attempts have been made to substitute sulphuric acid with different catalysts. [27][28][29] The Beckmann rearrangement is performed in a highly acidic media (H 2 SO 4 ) or a combination of acetic acid, acetic anhydride, and hydrogen chloride. Because these chemicals are incompatible with a wide number of sensitive substrates.…”

Section: Various Attempts Have Been Undertaken To Perform the Beckman...mentioning

confidence: 99%

Comprehensive updates on Beckmann Rearrangement

Kaushik,

Jain,

Malik

et al. 2024

ChemistrySelect

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Beckmann rearrangement has been quite successful in the preparation of many medicinally potent scaffolds. In synthetic organic chemistry, the Beckmann rearrangement is quite popular, caprolactam is synthesized from cyclohexanone oxime on a large scale for Nylon‐6 production. The function of numerous catalysts and media in the Beckmann rearrangement has been discussed in depth in this review. In the last 20 years, Beckmann rearrangement catalysis has evolved from a potentially hazardous to a more environmentally friendly catalyst, as a result of greater usage. Catalytic performance and synthetic performance of various catalytic systems have been re‐evaluated in the present review article.

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“…Among the recently developed heterogeneous catalysts for cross-coupling reactions there are various supported catalysts, including palladium loaded mesoporous silica [19][20][21][22][23], metal and graphene oxides [24][25][26], zeolites [27][28][29], and organic supports, such as polymers and dendrimers [30][31][32][33][34][35]. Dendrimers are one of the most versatile macromolecular platforms for the stabilization of catalytically active metal complexes or nanoparticles (NPs) because of their hyperbranched architecture [36].…”

Section: Introductionmentioning

confidence: 99%

Magnetically Recoverable Nanoparticulate Catalysts for Cross-Coupling Reactions: The Dendritic Support Influences the Catalytic Performance

et al. 2021

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Carbon-carbon cross-coupling reactions are among the most important synthetic tools for the preparation of pharmaceuticals and bioactive compounds. However, these reactions are normally carried out using copper, phosphines, and/or amines, which are poisonous for pharmaceuticals. The use of nanocomposite catalysts holds promise for facilitating these reactions and making them more environmentally friendly. In the present work, the PEGylated (PEG stands for poly(ethylene glycol) pyridylphenylene dendrons immobilized on silica loaded with magnetic nanoparticles have been successfully employed for the stabilization of Pd2+ complexes and Pd nanoparticles. The catalyst developed showed excellent catalytic activity in copper-free Sonogashira and Heck cross-coupling reactions. The reactions proceeded smoothly in green solvents at low palladium loading, resulting in high yields of cross-coupling products (from 80% to 97%) within short reaction times. The presence of magnetic nanoparticles allows easy magnetic separation for repeated use without a noticeable decrease of catalytic activity due to the strong stabilization of Pd species by rigid and bulky dendritic ligands. The PEG dendron periphery makes the catalyst hydrophilic and better suited for green solvents. The minor drop in activity upon the catalyst reuse is explained by the formation of Pd nanoparticles from the Pd2+ species during the catalytic reaction. The magnetic separation and reuse of the nanocomposite catalyst reduces the cost of target products as well as energy and material consumption and diminishes residual contamination by the catalyst. These factors as well as the absence of copper in the catalyst makeup pave the way for future applications of such catalysts in cross-coupling reactions.

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Zeolite enslaved transition metal complexes as novel heterogeneous catalysts for synthesis of polycyclic heterocycles using suzuki--miyaura cross coupling reaction under greener conditions

Cited by 18 publications

References 24 publications

Synthesis and Theoretical Studies of Biologically Active Thieno Nucleus Incorporated Tri and Tetracyclic Nitrogen Containing Heterocyclics Scaffolds via Suzuki Cross‐Coupling Reaction

Synthesis and Theoretical Studies of Biologically Active Thieno Nucleus Incorporated Tri and Tetracyclic Nitrogen Containing Heterocyclics Scaffolds via Suzuki Cross‐Coupling Reaction

Comprehensive updates on Beckmann Rearrangement

Magnetically Recoverable Nanoparticulate Catalysts for Cross-Coupling Reactions: The Dendritic Support Influences the Catalytic Performance

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