An Efficient Approach to 2-CF<sub>3</sub>-Indoles Based on <i>ortho</i>-Nitrobenzaldehydes
The catalytic olefination reaction of 2-nitrobenzaldehydes with CF<sub>3</sub>CCl<sub>3</sub> afforded stereoselectively trifluoromethylated <i>ortho</i>-nitrostyrenes in up to 88% yield. The reaction of these alkenes with pyrrolidine permits preparation of α-CF&l...
| Published in: | Molecules |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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MDPI AG
2021-12-01
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| Online Access: | https://www.mdpi.com/1420-3049/26/23/7365 |
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| author | Vasiliy M. Muzalevskiy Zoia A. Sizova Vladimir T. Abaev Valentine G. Nenajdenko |
| author_facet | Vasiliy M. Muzalevskiy Zoia A. Sizova Vladimir T. Abaev Valentine G. Nenajdenko |
| author_sort | Vasiliy M. Muzalevskiy |
| collection | DOAJ |
| container_title | Molecules |
| description | The catalytic olefination reaction of 2-nitrobenzaldehydes with CF<sub>3</sub>CCl<sub>3</sub> afforded stereoselectively trifluoromethylated <i>ortho</i>-nitrostyrenes in up to 88% yield. The reaction of these alkenes with pyrrolidine permits preparation of α-CF<sub>3</sub>-β-(2-nitroaryl) enamines. Subsequent one pot reduction of nitro-group by Fe-AcOH-H<sub>2</sub>O system initiated intramolecular cyclization to afford 2-CF<sub>3</sub>-indoles. Target products can be prepared in up to 85% yields. Broad synthetic scope of the reaction was shown as well as some followed up transformations of 2- CF<sub>3</sub>-indole. |
| format | Article |
| id | doaj-art-9e8b3757e8ff4e399d65126908e622ad |
| institution | Directory of Open Access Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| spelling | doaj-art-9e8b3757e8ff4e399d65126908e622ad2025-08-19T22:44:10ZengMDPI AGMolecules1420-30492021-12-012623736510.3390/molecules26237365An Efficient Approach to 2-CF<sub>3</sub>-Indoles Based on <i>ortho</i>-NitrobenzaldehydesVasiliy M. Muzalevskiy0Zoia A. Sizova1Vladimir T. Abaev2Valentine G. Nenajdenko3Department of Chemistry, Lomonosov Moscow State University, 119899 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119899 Moscow, RussiaNorth Ossetian State University, 44-46 Vatutina St., 362025 Vladikavkaz, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119899 Moscow, RussiaThe catalytic olefination reaction of 2-nitrobenzaldehydes with CF<sub>3</sub>CCl<sub>3</sub> afforded stereoselectively trifluoromethylated <i>ortho</i>-nitrostyrenes in up to 88% yield. The reaction of these alkenes with pyrrolidine permits preparation of α-CF<sub>3</sub>-β-(2-nitroaryl) enamines. Subsequent one pot reduction of nitro-group by Fe-AcOH-H<sub>2</sub>O system initiated intramolecular cyclization to afford 2-CF<sub>3</sub>-indoles. Target products can be prepared in up to 85% yields. Broad synthetic scope of the reaction was shown as well as some followed up transformations of 2- CF<sub>3</sub>-indole.https://www.mdpi.com/1420-3049/26/23/7365CF<sub>3</sub>-groupcatalytic olefination reactionnitro groupreductionindolefluorine |
| spellingShingle | Vasiliy M. Muzalevskiy Zoia A. Sizova Vladimir T. Abaev Valentine G. Nenajdenko An Efficient Approach to 2-CF<sub>3</sub>-Indoles Based on <i>ortho</i>-Nitrobenzaldehydes CF<sub>3</sub>-group catalytic olefination reaction nitro group reduction indole fluorine |
| title | An Efficient Approach to 2-CF<sub>3</sub>-Indoles Based on <i>ortho</i>-Nitrobenzaldehydes |
| title_full | An Efficient Approach to 2-CF<sub>3</sub>-Indoles Based on <i>ortho</i>-Nitrobenzaldehydes |
| title_fullStr | An Efficient Approach to 2-CF<sub>3</sub>-Indoles Based on <i>ortho</i>-Nitrobenzaldehydes |
| title_full_unstemmed | An Efficient Approach to 2-CF<sub>3</sub>-Indoles Based on <i>ortho</i>-Nitrobenzaldehydes |
| title_short | An Efficient Approach to 2-CF<sub>3</sub>-Indoles Based on <i>ortho</i>-Nitrobenzaldehydes |
| title_sort | efficient approach to 2 cf sub 3 sub indoles based on i ortho i nitrobenzaldehydes |
| topic | CF<sub>3</sub>-group catalytic olefination reaction nitro group reduction indole fluorine |
| url | https://www.mdpi.com/1420-3049/26/23/7365 |
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