A Review on the Recent Multicomponent Synthesis of Pyranopyrazoles

Mamaghani, Manouchehr; Nia, Roghayeh Hossein

doi:10.1080/10406638.2019.1584576

Cited by 81 publications

(40 citation statements)

References 157 publications

(113 reference statements)

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“…All of the materials were of commercial reagent grade and were used without further purification. The synthesis and characterization of the studied compounds were previously reported [49]. Melting points of products were determined by Electro thermal 9200.…”

Section: Methodsmentioning

confidence: 99%

Green synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles] using Fe3O4@l-arginine as a robust and reusable catalyst

Ghasemzadeh

Mirhosseini‐Eshkevari

Abdollahi-Basir

2019

BMC Chemistry

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The synthesized Fe3O4@l-arginine showed strong catalytic performance in the one-pot synthesis of spiropyranopyrazoles via the reactions of hydrazines, β-keto esters, isatins, and malononitrile or ethyl cyanoacetate under solvent-free conditions. The biologically active heterocyclic compounds including spiropyranopyrazole derivatives were efficiently synthesized in short reaction times and excellent yields in the presence of Fe3O4/l-arginine at room temperature. The highlighted features of the Fe3O4@l-arginine nanocomposite are highly stable, easy to separate, low loading, cost-effective with easy preparation and reusability of the catalyst. The heterogeneous nanocomposite was fully characterized by SEM, EDX, FT-IR, XRD and TEM analysis.

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Section: Methodsmentioning

confidence: 99%

Green synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles] using Fe3O4@l-arginine as a robust and reusable catalyst

Ghasemzadeh

Mirhosseini‐Eshkevari

Abdollahi-Basir

2019

BMC Chemistry

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“…1 ). Because of the great importance and numerous utilizations of pyranopyrazole and its derivatives, modifying the procedure for its synthesis are at the top of scientific research 3 , 4 . Using heterogeneous nanocatalyst to synthesize pyranopyrazole has attracted great importance among previous methods on account of high efficiency.…”

Section: Introductionmentioning

confidence: 99%

Fe3O4@chitosan-tannic acid bionanocomposite as a novel nanocatalyst for the synthesis of pyranopyrazoles

Kamalzare

Ahghari

Bayat

et al. 2021

Sci Rep

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Recently magnetic nanocatalyst has attracted considerable attention because of its unique properties, including high performance, easy separation from the reaction mixture, and recyclability. In this study, a novel magnetic bionanocomposite was synthesized with chitosan and tannic acid as a natural material. The synthesized bionanocatalyst was characterized by essential analysis. Fe3O4@chitosan-tannic acid as a heterogeneous nanocatalyst was successfully applied to synthesize pyranopyrazole and its derivatives by a one-pot four-component reaction of malononitrile, ethyl acetoacetate, hydrazine hydrate, and various aromatic aldehyde. At the end of the reaction, the nanocatalyst was separated from the reaction mixture and was reused several times with no significant decrease in its catalytic performance. Simple purification of products, the ability for recovering and reusing the nanocatalyst, eco-friendliness, high yields of pure products, mild reaction conditions, short reaction time, non-toxicity, economically affordable are some of the advantages of using the fabricated nanocatalyst in the synthesis of pyranopyrazole.

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“…Chief among these are multiple pharmacological and biological properties, such as antioxidant, antibacterial, anti-molluscicidal, analgesic, antiviral potential, and inhibitors of human checkpoint kinase-1 [9]. Upon an extensive literature review, it was confirmed that the wide-range of pyrano-[2,3-c]-pyrazoles activities are linked to the structural base core of the condensed pyrane and pyrazole [10]. In this regard, researchers expended efforts on the development of a single structural framework by associating both motifs (pyrane and pyrazole) in the hope of enhancing the biological activity and pharmacological properties of this compound [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization of Pyrano-[2,3-c]-Pyrazoles Derivatives and Determination of Their Antioxidant Activities

Addoum

Khalfi

Idiken

et al. 2021

IJT

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Background: Antioxidants are developed to assist the immune system and overcome oxidative stress, the aggression of cellular constituents due to imbalance between reactive oxygen species and the inner antioxidant system. The main objective of this study was to search for new and potent antioxidants to protect humans against diseases associated with oxidative stress. Methods: In this study, three pyrano-[2,3-c]-pyrazole derivatives were synthesized via Multicomponent Reaction (MCR) approach and were characterized, using a melting point, High-Performance Liquid Chromatography (HPLC), and spectroscopic analyses (IR; 1H-NMR; 13C-NMR). All of the generated compounds were screened for their antioxidant properties in vivo, using ciliate “Tetrahymena” as a model organism exposed to oxidative and nitrative stress. They were then studied in vitro by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assays. Results: The results demonstrated that the three compounds (5a, b, c) are biologically active and possess potent antioxidant activities, especially the 5a and 5b derivatives. On the other hand, the in vitro bioassays revealed that the 5a derivative possessed a significant antioxidant activity much greater than ascorbic acid. Accordingly, the in silico data are consistent with the experimental data. Conclusion: These findings confirmed the potent antioxidant property of the synthesized compounds, providing us with new inspiration and challenges to design a library of pharmaceutical compounds with strong activity and low toxicity in the future.

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A Review on the Recent Multicomponent Synthesis of Pyranopyrazoles

Cited by 81 publications

References 157 publications

Green synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles] using Fe3O4@l-arginine as a robust and reusable catalyst

Green synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles] using Fe3O4@l-arginine as a robust and reusable catalyst

Fe3O4@chitosan-tannic acid bionanocomposite as a novel nanocatalyst for the synthesis of pyranopyrazoles

Synthesis, Characterization of Pyrano-[2,3-c]-Pyrazoles Derivatives and Determination of Their Antioxidant Activities

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