From Levulinic Acid to Biheterocycles: Synthesis of 1-[(5-Hydroxy-5-trifluoromethyl-3-substituted-4,5-dihydro-1<i>H</i>-pyrazol-1-yl)-3-(5-trifluoromethyl-1<i>H-</i>pyrazol-3-yl)propan-1-ones

Flores, Alex F. C.; Malavolta, Juliana L.; Frigo, Leandro Marcon; Doneda, Morgana; Flores, Darlene C.

doi:10.1080/00397911.2014.1003352

Cited by 5 publications

(2 citation statements)

References 14 publications

(11 reference statements)

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“…The reaction gave pyrazoles 267 and 268, correspondingly, in 94% yield. 117,118 In the same year, Wu and Wu synthesized difluoromethyl-and trifluoromethylcontaining pyrazoles of type 269−271. The products were obtained from fluorinated β-ethoxyenones (obtained by Cacylation of vinyl ethers) and p-nitrophenylhydrazine (Scheme 45).…”

Section: Condensation Of 13-dicarbonyl Equivalentsmentioning

confidence: 99%

“…In 2015, Flores treated trifluoromethyl-substituted enone 266 (obtained from levulinic acid) with hydrazine and phenylhydrazine (Scheme ). The reaction gave pyrazoles 267 and 268 , correspondingly, in 94% yield. , In the same year, Wu and Wu synthesized difluoromethyl- and trifluoromethyl-containing pyrazoles of type 269 – 271 . The products were obtained from fluorinated β-ethoxyenones (obtained by C-acylation of vinyl ethers) and p -nitrophenylhydrazine (Scheme ).…”

Section: Preparation Of Fluoroalkyl-substituted Pyrazolesmentioning

confidence: 99%

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Fluorinated Pyrazoles: From Synthesis to Applications

2020

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Fluorinated pyrazoles play an important role in medicinal chemistry, drug discovery, agrochemistry, coordination chemistry, and organometallic chemistry. Since the early 1990s, their popularity has grown exponentially. Moreover, more than 50% of all contributions on the topic have been published in the last 5 years. In this review, analysis of novel synthetic approaches to fluorinated pyrazoles that appeared in recent years is performed. A particular emphasis is devoted to a detailed consideration of reaction mechanisms. In addition, the reasons that have led to the ever-increasing popularity of fluorinated pyrazoles in various areas of science are discussed. At the end of the review, several potentially interesting but yet mostly unknown classes of fluorinated pyrazoles are outlined.

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Section: Condensation Of 13-dicarbonyl Equivalentsmentioning

confidence: 99%

Section: Preparation Of Fluoroalkyl-substituted Pyrazolesmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

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A Convenient Approach to CF₃‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one

et al. 2015

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New synthetic routes to trifluoromethylated N‐heterocycles based on condensations of 2‐methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one with bifunctional N‐nucleophiles are described. For the first time, trifluoromethyl‐containing pyrazoles, pyrazolines and isoxazolines bearing hydrazone or oxime groups could be obtained by a one‐pot strategy based on reactions of 5‐(trifluoromethyl)furan‐3(2H)‐one with two equivalents of the corresponding hydrazines or hydroxylamine in the presence of an acid. The interaction of furan‐3(2H)‐one with ureas proceeded under mild conditions to furnish 1H‐furo[2,3‐d]imidazol‐2(3H)‐one derivatives in good yield. Further, a trifluoromethyl‐containing quinoxaline derivative was obtained by condensation of furan‐3(2H)‐one with ortho‐phenylenediamine.

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(Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

et al. 2020

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An efficient approach to the preparation of β‐alkoxyenones bearing (het)aryl difluoromethyl substituents is described. The method included acylation of acyclic or cyclic vinyl ethers with (het)aryl difluoroacetyl chlorides. The method worked well for most substrates, except aryl‐substituted derivatives bearing electron‐donating groups in o‐ or p‐positions, and heteroaromatic compounds bearing sufficiently basic nitrogen atom. Synthetic utility of (het)aryl difluoromethyl‐substituted β‐alkoxyenones as CCC bis‐electrophiles was demonstrated by heterocyclizations with common 1,2‐ and 1,3‐bis‐nucleophiles leading to compounds with (het)aryl–CF2–(het)aryl motif, in particular (het)aryl difluoromethyl‐substituted pyrazoles, isoxazoles, and pyrimidines – promising chemotypes for drug discovery.

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From Levulinic Acid to Biheterocycles: Synthesis of 1-[(5-Hydroxy-5-trifluoromethyl-3-substituted-4,5-dihydro-1H-pyrazol-1-yl)-3-(5-trifluoromethyl-1H-pyrazol-3-yl)propan-1-ones

Cited by 5 publications

References 14 publications

Fluorinated Pyrazoles: From Synthesis to Applications

Fluorinated Pyrazoles: From Synthesis to Applications

A Convenient Approach to CF₃‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one

(Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

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From Levulinic Acid to Biheterocycles: Synthesis of 1-[(5-Hydroxy-5-trifluoromethyl-3-substituted-4,5-dihydro-1H-pyrazol-1-yl)-3-(5-trifluoromethyl-1H-pyrazol-3-yl)propan-1-ones

Cited by 5 publications

References 14 publications

Fluorinated Pyrazoles: From Synthesis to Applications

Fluorinated Pyrazoles: From Synthesis to Applications

A Convenient Approach to CF3‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one

(Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

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A Convenient Approach to CF₃‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one