Biological activity of some pyrazolone derivatives

Павлов, П. Т.; Goleneva, A. F.; Леснов, А. Е.; Prokhorova, T. S.

doi:10.1007/bf02645994

Cited by 37 publications

(24 citation statements)

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“…The first set of procedures utilizes the catalysis of the components with piperidine in ethanolic solution (19). The second set of methods involves the noncatalyzed tandem KnoevenagelÁMichael reaction under neutral conditions in either ethanol (20) or benzene (21) solutions. Although it affords the corresponding (4,4-arylmethylene)bis(1H-pyrazol)-5-ols in reliable 70Á 90% yields, the reaction requires 3Á12 h of initial reflux with a further 24 h under ambient temperature to go to completion.…”

Section: Introductionmentioning

confidence: 99%

An eco-friendly procedure for the efficient synthesis of arylidinemalononitriles and 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) in aqueous media

Gouda

Abu‐Hashem

2012

Green Chemistry Letters and Reviews

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Commercially available lithium hydroxide monohydrate (LiOH ×H 2 O) was found to be a novel ''dual activation'' catalyst for Knoevenagel condensation between malononitrile (1) or 3-methyl 1-phenyl-1H-pyrazol-5-(4H)-one (6) with aromatic aldehydes 2a Á e leading to an efficient and easy synthesis of arylidenemalononitriles 3a Á d and 4,4?-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) 7a Á c in short times. The reaction of aryl aldehydes with malononitrile afforded excellent yields after 1Á6 min in aqueous media at room temperature. In case of 3-methyl-1-phenyl-1H-pyrazol-5-(4H)-one (6) and aromatic aldehydes afforded good yields after 60Á75 min at 908C. LiOH

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Section: Introductionmentioning

confidence: 99%

An eco-friendly procedure for the efficient synthesis of arylidinemalononitriles and 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) in aqueous media

Gouda

Abu‐Hashem

2012

Green Chemistry Letters and Reviews

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“…Nevertheless, among the pyrazolone derivatives synthesized compound 3a showed analgesic activity in mice when dosed at 50 mg kg -1 as suspension in a 2% starch jelly. 30 Additionally, compound 3a was utilized to prepare the spirocyclohexanone derivative 6 of potential biological significance according to a similar but modified procedure reported in the literature (Scheme 2). 31 Thus compound 3a was converted to a diester derivative 4 as a result of Michael addition with excess of methylacrylate.…”

Section: Resultsmentioning

confidence: 99%

High speed synthesis of pyrazolones using microwave-assisted neat reaction technology

Pal¹,

Mareddy²,

Devi³

2008

J. Braz. Chem. Soc.

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Descrevemos uma síntese rápida e pratica de pirazolonas, na ausência de solvente, sob irradiação de microondas. Esta metodologia sintética envolve a reação de b-cetoésteres com hidrazinas substituídas e não-substituídas e oferece uma preparação simples e direta de diferentes pirazolonas com alta regioseletividade. Essas pirazolonas podem existir em diferentes formas tautoméricas em solução e o anel 2-aril-pirazol-3-ona permanece torcido em relação ao plano da pirazolona no estado cristalino. O mecanismo da reação é proposto levando em conta a regiosseletividade. Uma das pirazolonas obtidas nesse processo foi usada na preparação de um derivado espirociclohexanona de significativo potencial biológico.A high speed, solvent-free, and practical synthesis of pyrazolones under microwave irradiation is described. This greener synthetic methodology involves the reaction of b-keto ester with substituted or unsubstituted hydrazine and provides a simple and straightforward one-pot approach for the synthesis of a variety of pyrazolone derivatives with high regioselectivity. These pyrazolones can exist in different tautomeric forms in solution and the aryl ring of 2-aryl pyrazol-3-ones remain twisted with respect to the pyrazole plane in the crystal state. Mechanism of the reaction accounting the regioselectivity has been proposed. One of the pyrazolones obtained via this process was utilized to prepare a spirocyclohexanone derivative of potential biological significance.

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“…In recent years, different reagents were applied for the synthesis of 4,4'-(arylmethylene)bis(3-methyl -1-phenyl-pyrazol-5-ols) derivatives, some of them including condensation reaction between arylaldehydes and two equivalents of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (Li et al, 1998;Singh & Singh, 1984;Pavlov et al, 1998;Buzykin & Lonshchakova, 1971;Wang et al, 2005;Elinson et al, 2008;Sujatha et al, 2009;Niknam & Mirzaee, 2011;Mosaddegh et al, 2010;Zang et al, 2011;Tayebi et al, 2011). 1) and used as heterogeneous solid acid catalyst for the synthesis of 4,4'-alkylmethylene-bis(3-methyl-5-pyrazolones).…”

Section: Introducationmentioning

confidence: 99%

Synthesis of 4,4’-(Arylmethylene)bis(1H-pyrazol-5-ols) Using Silica-bonded Ionic Liquid as Recyclable Catalyst

Baghernejad¹,

Niknam²

2012

IJC

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Biological activity of some pyrazolone derivatives

Cited by 37 publications

References 0 publications

An eco-friendly procedure for the efficient synthesis of arylidinemalononitriles and 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) in aqueous media

An eco-friendly procedure for the efficient synthesis of arylidinemalononitriles and 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) in aqueous media

High speed synthesis of pyrazolones using microwave-assisted neat reaction technology

Synthesis of 4,4’-(Arylmethylene)bis(1H-pyrazol-5-ols) Using Silica-bonded Ionic Liquid as Recyclable Catalyst

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