Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF<sub>3</sub>-Ynones with NaN<sub>3</sub>: DFT Study of the Reaction Mechanism
A detailed study of the reaction of CF<sub>3</sub>-ynones with NaN<sub>3</sub> was performed. It was found that the reaction permits the selective synthesis of either 4-trifluoroacetyltriazoles or 5-CF<sub>3</sub>-isoxazoles. The chemoselectivity of the reaction w...
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MDPI AG
2022-11-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/23/23/14522 |
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| author | Vasiliy M. Muzalevskiy Zoia A. Sizova Mikhail S. Nechaev Valentine G. Nenajdenko |
| author_facet | Vasiliy M. Muzalevskiy Zoia A. Sizova Mikhail S. Nechaev Valentine G. Nenajdenko |
| author_sort | Vasiliy M. Muzalevskiy |
| collection | DOAJ |
| description | A detailed study of the reaction of CF<sub>3</sub>-ynones with NaN<sub>3</sub> was performed. It was found that the reaction permits the selective synthesis of either 4-trifluoroacetyltriazoles or 5-CF<sub>3</sub>-isoxazoles. The chemoselectivity of the reaction was switchable via acid catalysis. The reaction of CF<sub>3</sub>-ynones with NaN<sub>3</sub> in EtOH produced high yields of 4-trifluoroacetyltriazoles. In contrast, the formation of 5-CF<sub>3</sub>-isoxazoles was observed under catalysis by acids. This acid-switchable procedure can be performed at sub-gram scale. The possible reaction mechanism was supported by DFT calculations. The synthetic utility of the prepared 4-trifluoroacetyltriazoles was demonstrated. |
| first_indexed | 2024-03-09T17:47:47Z |
| format | Article |
| id | doaj.art-c26a07707715496796cc2f7aa1062227 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T17:47:47Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-c26a07707715496796cc2f7aa10622272023-11-24T11:03:33ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-11-0123231452210.3390/ijms232314522Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF<sub>3</sub>-Ynones with NaN<sub>3</sub>: DFT Study of the Reaction MechanismVasiliy M. Muzalevskiy0Zoia A. Sizova1Mikhail S. Nechaev2Valentine G. Nenajdenko3Department of Chemistry, Lomonosov Moscow State University, 119899 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119899 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119899 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119899 Moscow, RussiaA detailed study of the reaction of CF<sub>3</sub>-ynones with NaN<sub>3</sub> was performed. It was found that the reaction permits the selective synthesis of either 4-trifluoroacetyltriazoles or 5-CF<sub>3</sub>-isoxazoles. The chemoselectivity of the reaction was switchable via acid catalysis. The reaction of CF<sub>3</sub>-ynones with NaN<sub>3</sub> in EtOH produced high yields of 4-trifluoroacetyltriazoles. In contrast, the formation of 5-CF<sub>3</sub>-isoxazoles was observed under catalysis by acids. This acid-switchable procedure can be performed at sub-gram scale. The possible reaction mechanism was supported by DFT calculations. The synthetic utility of the prepared 4-trifluoroacetyltriazoles was demonstrated.https://www.mdpi.com/1422-0067/23/23/14522CF<sub>3</sub>-ynonessodium azidetriazolesisoxazolesCF<sub>3</sub>-group |
| spellingShingle | Vasiliy M. Muzalevskiy Zoia A. Sizova Mikhail S. Nechaev Valentine G. Nenajdenko Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF<sub>3</sub>-Ynones with NaN<sub>3</sub>: DFT Study of the Reaction Mechanism International Journal of Molecular Sciences CF<sub>3</sub>-ynones sodium azide triazoles isoxazoles CF<sub>3</sub>-group |
| title | Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF<sub>3</sub>-Ynones with NaN<sub>3</sub>: DFT Study of the Reaction Mechanism |
| title_full | Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF<sub>3</sub>-Ynones with NaN<sub>3</sub>: DFT Study of the Reaction Mechanism |
| title_fullStr | Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF<sub>3</sub>-Ynones with NaN<sub>3</sub>: DFT Study of the Reaction Mechanism |
| title_full_unstemmed | Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF<sub>3</sub>-Ynones with NaN<sub>3</sub>: DFT Study of the Reaction Mechanism |
| title_short | Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF<sub>3</sub>-Ynones with NaN<sub>3</sub>: DFT Study of the Reaction Mechanism |
| title_sort | acid switchable synthesis of trifluoromethylated triazoles and isoxazoles via reaction of cf sub 3 sub ynones with nan sub 3 sub dft study of the reaction mechanism |
| topic | CF<sub>3</sub>-ynones sodium azide triazoles isoxazoles CF<sub>3</sub>-group |
| url | https://www.mdpi.com/1422-0067/23/23/14522 |
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