Synthesis of fluorinated dipyrazolyl sulfones from bis(2-fluoro-2-polyfluoroalkylalkenyl) sulfones and diazomethane

Borodkin, Yaroslav S.; Русанов, Эдуард Б.; Khizhan, A. I.; Shermolovich, Yurii G.

doi:10.1007/s10593-019-02578-3

Cited by 3 publications

(3 citation statements)

References 6 publications

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“…In 2019, Shermolovich and co-workers synthesized fluorinated dipyrazolyl sulfones by reacting fluorovinyl sulfones with diazomethane ( 190 ) at room temperature (Scheme ). Products of type 191 – 196 were obtained on a gram scale. In each experiment, the formation of two isomers was observed: 191 (17%) and 192 (6%); 193 (41%) and 194 (32%); 195 (60%) and 196 (15%).…”

Section: Preparation Of Fluoroalkyl-substituted Pyrazolesmentioning

confidence: 99%

“…Scheme 21. [Ag]-Catalyzed Synthesis of CF 3 -Substituted Pyrazoles by[3 + 2] Cycloaddition of In Situ-Generated CF 3 CHN 2(90) with Formylchromones…”

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confidence: 99%

“…cycloaddition between diazo compound 188 and alkyne 177 took place. The formed intermediate 189 immediately underwent an intramolecular sigmatropic[1,5]-shift (van Alphen−Huẗtel rearrangement) to give pyrazole 185.In 2019, Shermolovich and co-workers synthesized fluorinated dipyrazolyl sulfones by reacting fluorovinyl sulfones with diazomethane(190) at room temperature (Scheme 31) 90. Products of type 191−196 were obtained on a gram scale.…”

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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: Preparation Of Fluoroalkyl-substituted Pyrazolesmentioning

confidence: 99%

“…Scheme 21. [Ag]-Catalyzed Synthesis of CF 3 -Substituted Pyrazoles by[3 + 2] Cycloaddition of In Situ-Generated CF 3 CHN 2(90) with Formylchromones…”

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Fluorinated Pyrazoles: From Synthesis to Applications

2020

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Modern Approaches to the Synthesis of Pyrazoles (A Review)

Baeva,

Gataullin

2024

Žurnal obŝej himii

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The article analyzes publications that present the results of studies of modern approaches to the synthesis of new and known heterocycles with a pyrazole fragment, as well as syntheses aimed at expanding the library of compounds of this series from hydrazines, hydrazides, semi- or thiosemicarbazides, diazo compounds, hydrazonyl chlorides. Some examples are shown that use approaches to the synthesis of pyrazoles through multicomponent reactions involving amines and hydroxamic acid or an amine and enaminoketone. References are provided to publications that reflect the results of studies of the biological activity of these heterocycles, the use of certain metals as selective extractants, the possibility of obtaining metal complexes with their participation, as well as some photochemical transformations.

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Isomeric bis(pyrazolyl)sulfones based on bis(1,1-dihydropolyfluoroalkyl)sulfones. A new type of ligands for metal-polymer complexes with silver cation

Borodkin¹,

Русанов²,

Shermolovich³

2021

Vopr. Khim. Khim. Tekhnol.

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The work is devoted to the methods of synthesis of bis(polyfluoroalkenyl)sulfones and bis(polyfluoromethoxyalkenyl)sulfones as well as to the study of their reactions with diazomethane, resulting in the formation of N-methylated bis(pyrazolyl)sulfones isomers. Methods for the preparation of bis(polyfluoromethoxyalkenyl)sulfones not described previously in the literature have been developed by the addition of triethylamine and trimethylchlorosilane to a solution of the respective bis(polyfluoroalkyl)sulfones and methanol in diethyl ether in an argon atmosphere. A new method for the preparation of a previously unknown bis(3,3-difluoro-2,2-dimethoxypropyl)sulfone was suggested. The reaction occurs at room temperature in methanol in the presence of lithium hydroxide monohydrate. It was found that different regioisomeric bis(polyfluoroalkylpyrazolyl)sulfones are formed when using different methoxy derivatives of bis(polyfluoroalkenyl)sulfones in reaction with diazomethane, depending on the length of the polyfluoroalkyl moiety. These experimental data suggest that the attack of the double bond of methoxy-derived bis(polyfluoroalkenyl)sulfones by a molecule of diazomethane is influenced not only by the presence of an alkoxyl group, but also by the length of the polyfluoroalkyl substituent. The obtained bis(pyrazolyl)sulfones were investigated for the possibility of their use as ligands in the chemistry of metal complexes. It was shown that 5,5'-sulfonylbis[4-(difluoromethyl)-1-methyl-1H-pyrazole] forms a polymeric metal complex with silver nitrate. The results of X-ray structural analysis of the prepared coordination compound are presented. According to these results, the silver atom coordinates with two nitrogen atoms of pyrazole cycles of different molecules in the crystal of the obtained metal-complex compound, forming a supramolecular structure. In our opinion, an important role in this arrangement is played by the nitrate group that is coordinated with two silver atoms. As a result, we observed a supramolecular structure in the crystal that had a spiral structure with some free space in the middle. The paper also presents the results of spectral and X-ray diffraction analysis of a new regioisomeric compound of bis(3-hexafluoropropyl-1-methylpyrazolyl)sulfone.

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Synthesis of fluorinated dipyrazolyl sulfones from bis(2-fluoro-2-polyfluoroalkylalkenyl) sulfones and diazomethane

Cited by 3 publications

References 6 publications

Fluorinated Pyrazoles: From Synthesis to Applications

Fluorinated Pyrazoles: From Synthesis to Applications

Modern Approaches to the Synthesis of Pyrazoles (A Review)

Isomeric bis(pyrazolyl)sulfones based on bis(1,1-dihydropolyfluoroalkyl)sulfones. A new type of ligands for metal-polymer complexes with silver cation

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