Hydromagnesite sheets impregnated with cobalt–ferrite magnetic nanoparticles as heterogeneous catalytic system for the synthesis of imidazo[1,2-<i>a</i>]pyridine scaffolds

Geedkar, Deepika; Kumar, Ashok; Kumar, Kranti; Sharma, Pratibha

doi:10.1039/d1ra02516c

Cited by 14 publications

(5 citation statements)

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“…More than dozens of reports are available on mechanistic aspects of one‐pot synthesis of imidazo[1,2‐ a ]pyridines, where most researchers proposed the formation of Schiff's base initially, followed by the reaction with alkynes [14,16,18,36–38] . Only one report is available by Ghosh et al., which deals with two mechanistic pathways for this reaction (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

“…More than dozens of reports are available on mechanistic aspects of one-pot synthesis of imidazo[1,2-a]pyridines, where most researchers proposed the formation of Schiff's base initially, followed by the reaction with alkynes. [14,16,18,[36][37][38] Only one report is available by Ghosh et al, which deals with two mechanistic pathways for this reaction (Scheme 2). They used NaHSO 4 .SiO 2 , along with CuI, as catalyst and found the formation of product at a faster rate through prior imine (5) formation in comparison to the propargyl alcohol (6) formation route.…”

Section: Catalytic Synthesis Of Substituted Imidazo[12-a]pyridinesmentioning

confidence: 99%

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Synthesis of Catalyst Using Bio‐benign Precursors and Its Application in One‐Pot Catalytic Synthesis of Imidazo[1,2‐a]pyridines

et al. 2023

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Development of catalysts using natural feedstock is the need of the current era, and accordingly, we have developed a new ligand N-(2-hydroxynapthylidene)-L-leucienyl-4,6-O-ethylideneβ-D-glucopyranosylamine using natural occurring D-glucose and L-amino acid. It interacts with several bio-relevant metal ions like iron, copper, zinc, etc., but its association with cupric ions is immune to pH (4.2-9.1) change. In-situ copper-catalyzed reactions have been proven to be pivotal in many important organic syntheses, including imidazo[1,2-a]pyridines, which is one of the important precursors of many drug molecules. Catalytic synthesis of imidazo[1,2-a]pyridines requires high catalyst loading, hazardous solvent, high temperature, and long reaction time, which are major drawbacks towards green synthetic methodology. Interestingly, our glycoconjugate-derived cupric complex catalyzes the reactions among aldehydes, 2-aminopyridines, and terminal alkynes under the solvent-free condition to afford one-pot synthesis of imidazo[1,2-a]pyridines and 23 derivatives have been reported in good to excellent yields (53-93 %) using lower reaction time, temperature, and catalyst loading compared to other reports on similar reactions. Hence, our approach enhances the green methodology towards the catalytic synthesis of imidazo[1,2-a]pyridine derivatives.

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Section: Resultsmentioning

confidence: 99%

Section: Catalytic Synthesis Of Substituted Imidazo[12-a]pyridinesmentioning

confidence: 99%

Synthesis of Catalyst Using Bio‐benign Precursors and Its Application in One‐Pot Catalytic Synthesis of Imidazo[1,2‐a]pyridines

et al. 2023

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“…Thin-layer chromatography (TLC) was performed using precoated aluminum sheets with silica gel 60F254. [53][54][55][56]…”

Section: Methodsmentioning

confidence: 99%

One-pot strategy to synthesize seven–membered 1,4-diazepine heterocyclic scaffolds assisted by zinc oxide nanoparticles as heterogeneous catalytic support system

Pandey¹,

Geedkar²,

Kumar³

2023

10.5267/j.ccl

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The present paper elicits the zinc oxide nanoparticles-assisted synthesis of a new series of seven-membered 1,4-diazepine heterocyclic compounds as potent lead scaffolds. Structures of synthesized compounds were corroborated using spectroanalytical techniques viz, FT-IR, 1H, 13C NMR, Mass, and elemental analysis. Also, Field emission scanning electron microscopy (FE-SEM), Transmission electron microscopy (TEM), Energy dispersive x-ray analysis (EDAX), powder X-ray diffraction (PXRD), and Fourier transform infrared spectroscopy (FT-IR) were used to establish the structure and morphology of the synthesized nanocatalyst. The clean workup procedure, high to excellent yields, relatively short reaction times, and high atom economy are the incredible advantages associated with the protocol.

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“…As the reaction time is very short, there was not a substantial elevation of temperature due to ultrasonic shock. The ultrasonic apparatus used showed the temperature automatically, so the temperature was controlled and fixed at room temperature by a water circulator in the case of any elevation of temperature. − The progress of the reaction was monitored through TLC (on aluminum sheets precoated with silica) using n -hexane/ethyl acetate (4:1) as the eluting system. After the completion of the reaction, 15.0 mL of 10 mol % sodium thiosulfate solution was added and extracted with ethyl acetate (3 × 20 mL).…”

Section: Methodsmentioning

confidence: 99%

“…Hence, encouraged by these advances, we sought to explore the relevance of these reagents and methods in the synthesis of fused imidazo-pyridine scaffolds. In continuation of our research program focused on the development of synthetic methodologies − herein, we wish to disclose for the first time the ultrasonic-assisted synthesis of 2-phenylimidazo[1,2- a ]pyridin-3-yl cyclohex-2-enones derivatives by employing iodine as a catalyst in aquatic conditions via one-pot MCR of 2-aminopyridine derivatives and pertinent aryl aldehydes along with dimedone embracing differently as one of the precursor substrates (Scheme ). To the best of our knowledge, the use of dimedone as a precursor for the synthesis of imidazo[1,2- a ]pyridine scaffolds by utilizing molecular iodine is hitherto unprecedented.…”

Section: Introductionmentioning

confidence: 99%

Molecular Iodine-Catalyzed Synthesis of Imidazo[1,2-a]Pyridines: Screening of Their In Silico Selectivity, Binding Affinity to Biological Targets, and Density Functional Theory Studies Insight

2022

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The present paper discloses an ultrasonication strategy assisted by molecular iodine as an environmentally benign catalyst leading to the synthesis of pharmacologically significant imidazo[1,2- a ]pyridine scaffolds. The molecular-iodine-catalyzed approach for the synthesis of biologically active synthetic equivalents was achieved through three-component coupling embracing 2-aminopyridine derivatives, pertinent acetophenones, and dimedone in water medium under aerobic conditions. The higher product yield (up to 96%) with a miniature reaction time and modest catalyst loading as demonstrated by higher ecological compatibility and sustainability factors are fascinating features of this protocol. The structures of synthesized compounds were accomplished through FT-IR, 1 H NMR, 13 C NMR, mass, and elemental analysis data. The virtual screening of synthetic moieties was performed to ascertain the in silico selectivity and binding affinities against several biological targets. Lipinski’s rules of five, ADMET, and TOPKAT descriptors were used to evaluate the drug-likeness assets. Furthermore, a quantum computational study was computed at the B3LYP/6-311G++(d,p) level of theory to investigate the density functional theory-based chemical reactivity parameters and HOMO–LUMO energy gap of the synthesized derivatives. The present studies open the way for in vitro and in vivo testing of synthesized derivatives as potent inhibitors with an improved pharmacological profile against farnesyl diphosphate synthase, phosphodiesterase III, CXCR4, and GABAa receptor agonists.

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Hydromagnesite sheets impregnated with cobalt–ferrite magnetic nanoparticles as heterogeneous catalytic system for the synthesis of imidazo[1,2-a]pyridine scaffolds

Abstract: Sustainable synthesis of imidazo[1,2-a]pyridine scaffolds assisted by hydromagnesite sheets impregnated with cobalt–ferrite (CoFe2O4-HMS) magnetic nanoparticles (MNPs).

Cited by 14 publications

References 48 publications

Synthesis of Catalyst Using Bio‐benign Precursors and Its Application in One‐Pot Catalytic Synthesis of Imidazo[1,2‐a]pyridines

Synthesis of Catalyst Using Bio‐benign Precursors and Its Application in One‐Pot Catalytic Synthesis of Imidazo[1,2‐a]pyridines

One-pot strategy to synthesize seven–membered 1,4-diazepine heterocyclic scaffolds assisted by zinc oxide nanoparticles as heterogeneous catalytic support system

Molecular Iodine-Catalyzed Synthesis of Imidazo[1,2-a]Pyridines: Screening of Their In Silico Selectivity, Binding Affinity to Biological Targets, and Density Functional Theory Studies Insight

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