Directed synthesis of 3-(2,2-dichlorocyclopropyl)pyrazoles

Kobelevskaya, Valentina А.; Popov, A.; Nikitin, A. Ya.; Levkovskaya, G. G.

doi:10.1134/s1070428017010298

Cited by 7 publications

(4 citation statements)

References 19 publications

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“…Furthermore, 3-vinylpyrazoles 71 react with dichlorocarbene, generated from chloroform or sodium trichloroacetate, to afford new cyclopropylpyrazoles 72 [ 77 ], which are interesting precursors of bisheterocycles such as 5-(pyrazol-4-yl)isoxazolines. Popov and coworkers synthesized 1 -t -butyl-3-(2,2-dichlorocyclopropyl)-1 H -pyrazole 72 by reaction of vinylpyrazole 71 with chloroform and sodium hydroxide under PTC.…”

Section: Reactivity Of Vinylpyrazolesmentioning

confidence: 99%

“…The reactions of 1-alkyl-5-chloro-3-vinyl-1 H -pyrazoles 73a – c under analogous conditions did not afford the target dichlorocyclopropane derivatives. In fact, 1-alkyl-5-chloro-3-(2,2-dichlorocyclopropyl)-1 H -pyrazoles 74a – c were obtained in good yield only when dichlorocarbene was generated under neutral conditions, by thermal decomposition of sodium trichloroacetate in chloroform in the presence of benzyltriethylammonium chloride (BTEAC) as PTC ( Scheme 27 ) [ 77 ].…”

Section: Reactivity Of Vinylpyrazolesmentioning

confidence: 99%

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Revisiting the Chemistry of Vinylpyrazoles: Properties, Synthesis, and Reactivity

Silva

2022

Molecules

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Vinylpyrazoles, also known as pyrazolyl olefins, are interesting motifs in organic chemistry but have been overlooked. This review describes the properties and synthetic routes of vinylpyrazoles and highlights their versatility as building blocks for the construction of more complex organic molecules. Concerning the reactivity of vinylpyrazoles, the topics surveyed herein include their use in cycloaddition reactions, free-radical polymerizations, halogenation and hydrohalogenation reactions, and more recently in transition-metal-catalyzed reactions, among other transformations. The current state of the art about vinylpyrazoles is presented with an eye to future developments regarding the chemistry of these interesting compounds. Styrylpyrazoles were not considered in this review, as they were the subject of a previous review article published in 2020.

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Section: Reactivity Of Vinylpyrazolesmentioning

confidence: 99%

Section: Reactivity Of Vinylpyrazolesmentioning

confidence: 99%

Revisiting the Chemistry of Vinylpyrazoles: Properties, Synthesis, and Reactivity

Silva

2022

Molecules

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“…The known methods for obtaining these practically important substances are complex and multi-stage, while the yields of the final products are low [100,101]. As a result of the search for new ways of recycling rocket fuel, as mentioned above, we have proposed an original method for the formation of functionally substituted pyrazoles or isoxazoles using heptyl (or hydroxylamine) or other reagents [102][103][104][105][106][107][108][109][110][111][112].…”

Section: Organylpyrazole Derivativesmentioning

confidence: 99%

The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry

Ларина

2022

Magnetochemistry

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This review summarizes the data on the stereochemical structure of functionalized azoles (pyrazoles, imidazoles, triazoles, thiazoles, and benzazoles) and related compounds obtained by multipulse and multinuclear 1H, 13C, 15N NMR spectroscopy and quantum chemistry. The stereochemistry of functionalized azoles is a challenging topic of theoretical research, as the correct interpretation of their chemical behavior and biological activity depends on understanding the factors that determine the stereochemical features and relative stability of their tautomers. NMR spectroscopy, in combination with quantum chemical calculations, is the most convenient and reliable approach to the evaluation of the stereochemical behavior of, in particular, nitrogen-containing heteroaromatic and heterocyclic compounds. Over the last decade, 15N NMR spectroscopy has become almost an express method for the determination of the structure of nitrogen-containing heterocycles.

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“…After getting the variable products by using chloroform/NaOH in presence of TBAC, our goal was to versatile intermediate, gem-dichlorocyclopropane by following the reported methods such as trichloro acetic acid sodium salt in chloroform in presence of nbutylammonium salts [31][32][33] to our surprise we obtained conjugate Michael addition 34 .…”

Section: Dratio = Diastereomers Ratiomentioning

confidence: 99%

Diastereoselective Synthesis of Spiro and Chlorocyclopropanes from Camphorpyrazolidinone derived -Unsaturated Amides

Gondi

2020

Preprint

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Directed synthesis of 3-(2,2-dichlorocyclopropyl)pyrazoles

Cited by 7 publications

References 19 publications

Revisiting the Chemistry of Vinylpyrazoles: Properties, Synthesis, and Reactivity

Revisiting the Chemistry of Vinylpyrazoles: Properties, Synthesis, and Reactivity

The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry

Diastereoselective Synthesis of Spiro and Chlorocyclopropanes from Camphorpyrazolidinone derived -Unsaturated Amides

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