New Bis(chalcones) and Their Transformation into Bis(pyrazoline) and Bis(pyrazole) Derivatives

Pinto, Diana; Silva, Artur M. S.; Cavaleiro, José A. S.; Elguero, José

doi:10.1002/ejoc.200390117

Cited by 64 publications

(41 citation statements)

References 19 publications

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“…Considerable improvement has been focused on the comparison of the results with the literature and the two efficient methods together. El-Rayyes and Al-Johary (1985) prepared similar pyrazolines in several hours, Pinto, et al, 2003, also prepared bis-pyrazoline in 24 h (Pinto, et al, 2003). While, in this work, products were obtained in good yields and shorter reaction times, about 60 min in ultrasound method.…”

Section: Resultsmentioning

confidence: 60%

Ultrasound-assisted Synthesis of Some New Curcumin Analogs and Their Corresponding Pyrazoline Derivatives

Hawaiz

Omer

2017

ARO

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Abstract-In this work, a series of new curcumin mono-carbonyl analogs containing benzyloxy moieties and their pyrazoline derivatives were synthesized using a green method (ultrasound assisted technique) along with traditional method. The work also includes a comparison between the two methods together and with the reported results. Remarkable improvements were achieved by dropping down the reaction time from hours to minutes and obtaining higher yields of the products.

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Section: Resultsmentioning

confidence: 60%

Ultrasound-assisted Synthesis of Some New Curcumin Analogs and Their Corresponding Pyrazoline Derivatives

Hawaiz

Omer

2017

ARO

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“…According to our literature surveys, compound 3a is known the others are unknown. 18 The structures of compounds were explained on the basis of spectral data (NMR, IR) and elemental analysis.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and anti-bacterial activity of novel 1,3-pheylene-bis-N-acetyl- and N-phenylpyrazole derivatives

Demir¹,

Gürdere²,

Ceylan³

et al. 2017

Org. Commun.

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Abstract:The 1,1'-(5,5'-(1,3-phenylene)bis(3-aryl-4,5-dihydro-1H-pyrazole-5,1-diyl))di-ethanone (5a-e) and 1,3-bis(1-phenyl-3-(aryl)-4,5-dihydro-1H-pyrazol-5-yl)benzene (6a-e) were synthesized by addition of hydrazine hydrate and/or phenylhydrazine to 1,3-phenylene-bis-chalcone derivatives (3a-e), respectively. The structures of obtained compounds (5a-e and 6a-e) were characterized using the spectroscopic methods (NMR, IR) and elemental analysis. Addition, the in vitro antibacterial activities of compounds (5a-e) was tested against the five human pathogenic bacteria. Gentamycin and Fluconazole were used as positive control. The results were given as inhibition zone (mm) and the compounds 5d and 5e showed the same activity with standard (Fluconazole) against C. albinas.

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“…It was postulated that the α,β-unsaturated ketone moiety reacts first with one hydrazine molecule and then the chromone moiety reacts with a second molecule, leading to the formation of pyrazolyl-2-pyrazoline derivatives. 6 Following this work and our interest on the synthesis and structural characterization of bis-1,2-azoles, 6,12 we treated 3-(3-aryl-3-oxopropenyl)chromen-4-ones 1a-g with an excess of phenylhydrazine in refluxing acetic acid and novel pyrazolyl-2-pyrazolines 2a-g were obtained in good yields (62-73%) (Scheme 1).…”

Section: Synthesismentioning

confidence: 99%

“…In the continuation of an on-going research program devoted to the synthesis and characterization of these bis-heterocyclic ring systems, 6,12 it seemed to be a challenging task to study the reaction of 3-(3-aryl-3-oxopropenyl)chromen-4-ones 1 with substituted hydrazines. Our work in this chemical transformation and a detailed NMR analysis of the structural features of the novel pyrazolyl-2-pyrazolines will be presented and discussed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structure elucidation of novel pyrazolyl-2-pyrazolines obtained by the reaction of 3-(3-aryl-3-oxopropenyl)chromen-4-ones with phenylhydrazine

Santos¹,

Silva²,

Jekő³

et al. 2012

Arkivoc

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Novel 3-aryl-5-{4-[5-(2-hydroxyphenyl)-1-phenylpyrazolyl]}-2-pyrazolines 2a-g have been prepared by the treatment of 3-(3-aryl-3-oxopropenyl)chromen-4-ones 1a-g with phenylhydrazine in refluxing acetic acid. NMR studies on deuteriochloroform solutions of pyrazolyl-2-pyrazolines 2a-g at different temperatures showed that at room temperature a mixture of diastereomers are present. This diastereoselectivity arises from the combination of the pyrazoline C-4 stereocenter and two planar chiral subunits due to internal steric hindrance. The energy barriers of this steric hindrance were overcome in DMSO-d 6 solutions at 60 o C. The acetylation of some pyrazolyl-2-pyrazoline derivatives 2a-c,e helped to confirm the presence of the referred mixture of diastereomers.

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New Bis(chalcones) and Their Transformation into Bis(pyrazoline) and Bis(pyrazole) Derivatives

Cited by 64 publications

References 19 publications

Ultrasound-assisted Synthesis of Some New Curcumin Analogs and Their Corresponding Pyrazoline Derivatives

Ultrasound-assisted Synthesis of Some New Curcumin Analogs and Their Corresponding Pyrazoline Derivatives

Synthesis and anti-bacterial activity of novel 1,3-pheylene-bis-N-acetyl- and N-phenylpyrazole derivatives

Synthesis and structure elucidation of novel pyrazolyl-2-pyrazolines obtained by the reaction of 3-(3-aryl-3-oxopropenyl)chromen-4-ones with phenylhydrazine

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