Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes
| Autor: | Pavel K. Mykhailiuk |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Component (thermodynamics)
Chemistry Organic Chemistry chemistry.chemical_element pentafluoroethyl group Electron Pyrazole Medicinal chemistry Cycloaddition Full Research Paper lcsh:QD241-441 pyrazole chemistry.chemical_compound Column chromatography lcsh:Organic chemistry fluorine Fluorine Organic chemistry lcsh:Q lcsh:Science pentafluoroethyldiazomethane cycloaddition Dichloromethane |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 11, Iss 1, Pp 16-24 (2015) |
| ISSN: | 1860-5397 |
| Popis: | A one-pot reaction between C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes gives C2F5-substituted pyrazoles in excellent yields. The transformation smoothly proceeds in dichloromethane/water, tolerates the presence of air, and requires no purification of products by column chromatography. Mechanistically, C2F5CH2NH2·HCl and NaNO2 react first in water to generate C2F5CHN2, that participates in a [3 + 2] cycloaddition with electron-deficient alkynes in dichloromethane. |
| Databáze: | OpenAIRE |
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