One-pot multicomponent synthesis of unsymmetrical polyhydroquinoline derivatives with 1,1′-butylenebispyridinium hydrogen sulfate as an efficient, halogen-free and reusable Brönsted ionic liquid catalyst

Khaligh, Nader Ghaffari

doi:10.1016/s1872-2067(14)60087-5

Cited by 20 publications

(4 citation statements)

References 79 publications

(65 reference statements)

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“…Finally, the targeted compounds 1,3‐diarylpyrazole incorporated polyhydroquinoline derivatives ( 6 a–j , 7 a–j and 8 a–j ) were synthesized by condensation of 1,3‐diarylpyrazole‐4‐carbaldehyde derivatives 1 a–e, alicyclic 1,3‐diketone 2 a–b , alkyl acetoacetate 3, 4, 5 and ammonium acetate in 1,1′‐butylenebispyridinium hydrogen sulfate (Bbpy)(HSO 4 ) 2 ionic liquid as reaction medium as well as catalyst under microwave irradiation as a source of energy at 350 watts power level.…”

Section: Resultsmentioning

confidence: 99%

“…Task‐specific ionic liquids (TSILs) have been used as valuable substitutes for volatile organic solvents and are environmentally benign catalysts and reagents in chemical procedures . Recently, binuclear Brönsted acidic ionic liquid consisiting of pyridine nuclues were prepared and their catalytic activity was studied for Hantzsch reaction condition leading to polyhydroquinoline derivatives …”

Section: Introductionmentioning

confidence: 99%

“…[27] Recently, binuclear Brö nsted acidic ionic liquid consisiting of pyridine nuclues were prepared and their catalytic activity was studied for Hantzsch reaction condition leading to polyhydroquinoline derivatives. [28] In continuation of our efforts to synthesize some novel heterocyclic motifs with diverse biological activities, [29] we discuss herein the microwave assisted synthesis of novel polyhydroquinoline derivatives bearing diarylpyrazole motif in 1,1'-butylenebispyridinium hydrogen sulfate (Bbpy)(HSO 4 ) 2 as reaction medium and catalyst as well. Further, to get an insight of their pharmacological potency and obtain novel active entities for further optimization, the synthesized entities were screened for antimicrobial, antitubercular, antimalarial outcome against various pathogenic strains as well as toxicity against Vero cells.…”

Section: Introductionmentioning

confidence: 99%

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Microwave‐Assisted Synthesis of Novel Pyrazole Clubbed Polyhydroquinolines in an Ionic‐Liquid and their Biological Perspective

et al. 2018

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A series of diarylpyrazole clubbed polyhydroquinoline derivatives (6a‐j, 7a‐j, 8a‐j) were synthesized by one pot multicomponent methodology using ionic liquid (Bbpy)(HSO4)2 as solvent as well as catalyst under microwave irradiation as energy source. The synthesized entities were further screened in vitro for their preliminary biocidal potency against group of pathogenic bacterial as well as fungal strains; against M. tuberculosis H37Rv strain for antituberculosis activity and against P. falciparum to evaluate antimalarial potency. A number of compounds were found to render antibacterial activity against bacterial strains as compared to standard drugs. Compounds 6b, 6 f, 8e and 8j were found to possess higher antibacterial potency as compared to ampicillin as well as comparable to ciprofloxacin and chloramphenicol. The compounds 6e, 6j, 7e, 7j and 8j (MIC: 100 μg/mL) were found to be highly potent as antifungal candidates against C. albicans as compared to griseofulvin. For antituberculosis activity, compounds 8e, 8 h and 8j were found to be potent candidates against M. tuberculosis H37Rv strain as compared to rifampicin. Compounds 7a, 7c, 7d, 7 f, 7 h, 8d and 8i were found to be highly potent as compared to quinine (0.268 μg/mL) and comparable activity as to chloroquine (0.020 μg/mL). The cytotoxicity of the synthesized compounds was evaluated against Vero cell proving their non‐toxic behavior.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Microwave‐Assisted Synthesis of Novel Pyrazole Clubbed Polyhydroquinolines in an Ionic‐Liquid and their Biological Perspective

et al. 2018

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“…[12][13][14] The method for synthesis of PHQs involves a multicomponent Hantzsch reaction of an aldehyde with cyclic 1,3-diketone, ethyl acetoacetate, and ammonia acetate in an acid catalyst. 4,15 Alternatively, the Hantzsch reaction for the synthesis of polyhydroquinolines was recently studied using crosslinked poly(-AMPS-co-AA), 16 magnetic Fe 3 O 4 nanoparticles, 17 Brönsted ionic liquid, 18 lactate-water, 20 microwave irradiation, 21 organocatalysts, 22 ZnObeta zeolite, 23 p-TSA 24 and vanadium dodecylamino phosphate. 25 However, these methods suffer from drawbacks, such as the use of complex metal catalysts, the use of expensive reagents, difficult workup, corrosion problems, effluent pollution and non-recoverable catalysts.…”

Section: Introductionmentioning

confidence: 99%

Multicomponent synthesis of novel hybrid PHQ-fatty acids

et al. 2015

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Multicomponent reactions as methods for green synthesis are important pathways for obtaining of pharmacological compounds. In this work, an efficient synthesis of new fatty Hantzsch derivative compounds using a four-component reaction is described. We demonstrate for the first time a fatty acid polyhydroquinoline (hybrid PHQ-fatty acids) synthesis from renewable resources containing C16 and C18 saturated and unsaturated fatty chains, including the ricinoleic acid (12-hydroxy-9-cis-octadecenoic acid), the major constituent of castor oil. The experimental results demonstrate that the best value for charging the sulfamic acid was 20 mol% and that thirty new hybrids PHQ-fatty acids were synthesised in good yields.

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Bioinspired AgNPs: Effective and Recyclable Catalysts towards the One‐Pot Synthesis of Hexahydroquinoline Derivatives via Three‐Component Coupling Reaction

Bera

Mondal

Das³

et al. 2021

ChemistrySelect

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Green synthesis of silver nanoparticles (AgNPs) was carried out using aqueous bark extract of Shorea robusta(Sal tree) as the reducing and capping agent. AgNPs were characterized using modern characterization tools like UV-Vis, PXRD, FT-IR, SEM, and HR-TEM. The catalytic application of the prepared AgNPs in three-component coupling reaction of aldehyde, malononitrile, and cyclic enamino ketone resulted in good to excellent yields of hexahydroquinoline derivatives. Moreover, the catalyst can be recycled up to 5 times without compromising too much yield. The mechanistic pathway was investigated employing GC-Mass spectroscopy and supported through the Density Functional Theory (DFT) calculations. A two-step mechanism has been proposed for the coupling reaction, and the presence of electron-withdrawing group in the aldehyde component is found to be more favorable than electron-releasing one in terms of yield with lesser time.

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One-pot multicomponent synthesis of unsymmetrical polyhydroquinoline derivatives with 1,1′-butylenebispyridinium hydrogen sulfate as an efficient, halogen-free and reusable Brönsted ionic liquid catalyst

Cited by 20 publications

References 79 publications

Microwave‐Assisted Synthesis of Novel Pyrazole Clubbed Polyhydroquinolines in an Ionic‐Liquid and their Biological Perspective

Microwave‐Assisted Synthesis of Novel Pyrazole Clubbed Polyhydroquinolines in an Ionic‐Liquid and their Biological Perspective

Multicomponent synthesis of novel hybrid PHQ-fatty acids

Bioinspired AgNPs: Effective and Recyclable Catalysts towards the One‐Pot Synthesis of Hexahydroquinoline Derivatives via Three‐Component Coupling Reaction

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