Catalyst-free domino reaction in water/ethanol: an efficient, regio- and chemoselective one-pot multi-component synthesis of pyranopyrazole derivatives

Koohshari, Majid; Dabiri, Minoo; Salehi, Peyman

doi:10.1039/c3ra47639a

Cited by 38 publications

(18 citation statements)

References 18 publications

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“…A catalyst‐free approach to synthesize non‐spiro and spiropyranopyrazole derivatives via chemo and regioselective multicomponent reaction of hydrazine monohydrate 21 , propanedinitrile 23 /ethyl cyanoacetate, different aromatic aldehydes/isatin 40 /acenaphthenquinone 44 and dialkyl 3‐oxo pentanedioate 50 in water/ethanol without using any catalyst was reported by Koohshari et al in 2014. [ 41 ] 3‐Bromobenzaldehyde 51 and unsubstituted isatin 40 were more reactive among other carbonyl compounds and gave 78% and 85% yields of the products, respectively. Acenaphthenequinone 44 was also used in the four‐component reaction, which gave the highest 87% yield of the desired spiropyranopyrazole 53 (Scheme 10).…”

Section: Review Of the Literaturementioning

confidence: 99%

Synthesis of pyrano[2,3‐c]pyrazoles: A review

Sikandar

Zahoor

2020

Journal of Heterocyclic Chem

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One‐pot synthesis of pyrano[2,3‐c]pyrazole derivatives via two or multicomponent condensation of β‐ketoesters, hydrazine monohydrate/phenyl hydrazine, malononitrile, and substituted benzaldehydes is of great interest not only in synthetic chemistry but also in medicinal chemistry because of the tremendous biological activities, such as anticancer, anti‐inflammatory, analgesic, antimicrobial, and enzyme inhibitory activities exhibited by pyranopyrazoles. This review provides extensive knowledge on novel synthetic methodologies of biologically active non‐spiro/spiro‐pyrano[2,3‐c]pyrazole derivatives published recently.

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Section: Review Of the Literaturementioning

confidence: 99%

Synthesis of pyrano[2,3‐c]pyrazoles: A review

Sikandar

Zahoor

2020

Journal of Heterocyclic Chem

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“…It is worth mentioning that Pyranopyrazoles are composed of pyrazoles and pyrans which are the very important classes of heterocyclic compounds. Pyranopyrazoles exhibit significant biological properties such as anticancer, [ 51 ] antimicrobial, [ 52 ] anti‐inflammatory, [ 53 ] molluscicidal activities, [ 54,55 ] Chk1 kinase inhibitor, [ 56 ] potential insecticidal, [ 53 ] antiviral, [ 54 ] vasodilator [ 57 ] and analgesic. [ 58 ] Likewise, tetrazole derivatives have been used in drugs i.e.…”

Section: Introductionmentioning

confidence: 99%

Copper and nickel immobilized on cytosine@MCM‐41: as highly efficient, reusable and organic–inorganic hybrid nanocatalysts for the homoselective synthesis of tetrazoles and pyranopyrazoles

Nikoorazm

Tahmasbi

Gholami

et al. 2020

Applied Organom Chemis

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In this work, a green approach is reported for efficient synthesis of biologically active tetrazole and pyranopyrazole derivatives in the presence of Cu-Cytosine@MCM-41 and Ni-Cytosine@MCM-41 (copper (II) and nickel (II) catalyst on the modified MCM-41 using cytosine). The synthesis of tetrazoles and pyranopyrazoles in the presence of these catalysts was performed in green solvents such as water or poly (ethylene glycol) (PEG). All products were obtained in high TOF (turnover frequency) numbers in the presence of these catalysts, which indicate the high efficiency of these catalysts in the synthesis of tetrazole and pyranopyrazole derivatives. The prepared catalysts were characterized by various techniques such as BET, TGA, XRD, FT-IR, SEM, EDS, WDX, TEM, and AAS. Mesoporous structure of these catalysts was confirmed by nitrogen adsorptiondesorption isotherms. These catalysts can be recovered and reused for several runs without significant change in their catalytic activity or metal capacity. The recovered catalysts have been characterized by XRD, SEM, EDS, WDX, FT-IR and AAS techniques, by which their heterogeneous nature has been confirmed. K E Y W O R D S copper (II), mesoporous MCM-41, nickel (II), pyranopyrazoles, tetrazoles

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“…The synthesis of pyrano[2,3-c]pyrazole derivatives has been described by a regio-and chemoselective four-component reaction of dialkyl 3-oxopentanedioate, an active carbonyl compound, hydrazine and malononitrile in water/ethanol as a green medium at 60 C for 12 h under catalystfree condition 43 A concise synthesis of 6-amino-4-aryl-3-(trifluoromethyl)-1,4-dihydro-1-phenylpyrano[2,3c]pyrazole-5-carbonitriles (9) was performed effectively in aqueous media without catalyst by the reaction of aryl aldehydes, malononitrile, and 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one at 90 C 44 (Scheme 10). The synthesis of dihydropyrano[2,3-c]pyrazoles using ball milling technique without catalyst and solvent was also reported.…”

Section: Introductionmentioning

confidence: 99%

A Review on the Recent Multicomponent Synthesis of Pyranopyrazoles

Mamaghani

Nia

2019

Polycyclic Aromatic Compounds

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Due to biological and medicinal properties of pyranopyrazoles, synthesis of these bioactive heterocycles has attracted the interest of medicinal and organic chemists. This review focuses on the recent developments in multicomponent synthesis of pyranopyrazole and spiroconjugated pyranopyrazole systems. The present review describes the literature reports for the period 2005 to 2018. These reported approaches were performed in the classical and nonclassical conditions, particularly recent reports includes protocols under a green condition such as using catalyst, green solvents, and solvent-free conditions. ARTICLE HISTORY

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Catalyst-free domino reaction in water/ethanol: an efficient, regio- and chemoselective one-pot multi-component synthesis of pyranopyrazole derivatives

Cited by 38 publications

References 18 publications

Synthesis of pyrano[2,3‐c]pyrazoles: A review

Synthesis of pyrano[2,3‐c]pyrazoles: A review

Copper and nickel immobilized on cytosine@MCM‐41: as highly efficient, reusable and organic–inorganic hybrid nanocatalysts for the homoselective synthesis of tetrazoles and pyranopyrazoles

A Review on the Recent Multicomponent Synthesis of Pyranopyrazoles

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