An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes
The catalyst-free conjugate addition of pyrroles to β-Fluoro-β-nitrostyrenes was investigated. The reaction was found to proceed under solvent-free conditions to form 2-(2-Fluoro-2-nitro-1-arylethyl)-1<i>H</i>-pyrroles. The effectiveness of this approach was demonstrated through the prep...
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| Format: | Article |
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MDPI AG
2021-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/12/3515 |
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| author | Alexander S. Aldoshin Andrey A. Tabolin Sema L. Ioffe Valentine G. Nenajdenko |
| author_facet | Alexander S. Aldoshin Andrey A. Tabolin Sema L. Ioffe Valentine G. Nenajdenko |
| author_sort | Alexander S. Aldoshin |
| collection | DOAJ |
| description | The catalyst-free conjugate addition of pyrroles to β-Fluoro-β-nitrostyrenes was investigated. The reaction was found to proceed under solvent-free conditions to form 2-(2-Fluoro-2-nitro-1-arylethyl)-1<i>H</i>-pyrroles. The effectiveness of this approach was demonstrated through the preparation of a series of the target products in a quantitative yield. The kinetics of a conjugate addition of pyrrole was studied in detail to reveal the substituent effect and activation parameters of the reaction. The subsequent base-induced elimination of nitrous acid afforded a series of novel 2-(2-Fluoro-1-arylvinyl)-1<i>H</i>-pyrroles prepared in up to an 85% isolated yield. The two-step sequence herein proposed is an indispensable alternative to a direct reaction with elusive and unstable 1-Fluoroacetylenes. |
| first_indexed | 2024-03-10T10:34:10Z |
| format | Article |
| id | doaj.art-701b8037b5974b33b851c0dc691d0dd1 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T10:34:10Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-701b8037b5974b33b851c0dc691d0dd12023-11-21T23:24:10ZengMDPI AGMolecules1420-30492021-06-012612351510.3390/molecules26123515An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-NitrostyrenesAlexander S. Aldoshin0Andrey A. Tabolin1Sema L. Ioffe2Valentine G. Nenajdenko3Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1, 119991 Moscow, RussiaThe catalyst-free conjugate addition of pyrroles to β-Fluoro-β-nitrostyrenes was investigated. The reaction was found to proceed under solvent-free conditions to form 2-(2-Fluoro-2-nitro-1-arylethyl)-1<i>H</i>-pyrroles. The effectiveness of this approach was demonstrated through the preparation of a series of the target products in a quantitative yield. The kinetics of a conjugate addition of pyrrole was studied in detail to reveal the substituent effect and activation parameters of the reaction. The subsequent base-induced elimination of nitrous acid afforded a series of novel 2-(2-Fluoro-1-arylvinyl)-1<i>H</i>-pyrroles prepared in up to an 85% isolated yield. The two-step sequence herein proposed is an indispensable alternative to a direct reaction with elusive and unstable 1-Fluoroacetylenes.https://www.mdpi.com/1420-3049/26/12/3515β-Fluoro-β-nitrostyrenevinylpyrroleMichael additioneliminationkineticsHammett equation |
| spellingShingle | Alexander S. Aldoshin Andrey A. Tabolin Sema L. Ioffe Valentine G. Nenajdenko An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes Molecules β-Fluoro-β-nitrostyrene vinylpyrrole Michael addition elimination kinetics Hammett equation |
| title | An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes |
| title_full | An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes |
| title_fullStr | An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes |
| title_full_unstemmed | An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes |
| title_short | An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes |
| title_sort | easy synthesis of monofluorinated derivatives of pyrroles from β fluoro β nitrostyrenes |
| topic | β-Fluoro-β-nitrostyrene vinylpyrrole Michael addition elimination kinetics Hammett equation |
| url | https://www.mdpi.com/1420-3049/26/12/3515 |
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