Synthesis and Reactions of 3-Halogenated 2-CF<sub>3</sub>-Indoles
Halogenation of 2-trifluoromethylindole afforded 3-chloro-, 3-bromo- and 3-iodo derivatives in up to 98% yield. Methyl-, benzyl- and tosyl-groups can be installed at the nitrogen atom of prepared indoles in high yields by base catalyzed reaction with the corresponding alkylating (sulfonylating) reag...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/24/8822 |
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| author | Vasiliy M. Muzalevskiy Zoia A. Sizova Valentine G. Nenajdenko |
| author_facet | Vasiliy M. Muzalevskiy Zoia A. Sizova Valentine G. Nenajdenko |
| author_sort | Vasiliy M. Muzalevskiy |
| collection | DOAJ |
| description | Halogenation of 2-trifluoromethylindole afforded 3-chloro-, 3-bromo- and 3-iodo derivatives in up to 98% yield. Methyl-, benzyl- and tosyl-groups can be installed at the nitrogen atom of prepared indoles in high yields by base catalyzed reaction with the corresponding alkylating (sulfonylating) reagents. A high synthetic utility of the prepared haloindoles in the reaction with various nucleophilies was shown. The reaction with 4-methylthiophenol and copper cyanide afforded the corresponding sulfides and nitriles in high yield. Palladium catalyzed cross-coupling with phenyl boronic acid and phenylacetylene gave the corresponding 3-phenyl-2-CF<sub>3</sub>-indoles and acetylenic derivatives in 72–98% yield. |
| first_indexed | 2024-03-09T16:02:25Z |
| format | Article |
| id | doaj.art-91add31b85ce4691a8368497fbe1ecb0 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T16:02:25Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-91add31b85ce4691a8368497fbe1ecb02023-11-24T16:58:01ZengMDPI AGMolecules1420-30492022-12-012724882210.3390/molecules27248822Synthesis and Reactions of 3-Halogenated 2-CF<sub>3</sub>-IndolesVasiliy M. Muzalevskiy0Zoia A. Sizova1Valentine G. Nenajdenko2Department 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, RussiaHalogenation of 2-trifluoromethylindole afforded 3-chloro-, 3-bromo- and 3-iodo derivatives in up to 98% yield. Methyl-, benzyl- and tosyl-groups can be installed at the nitrogen atom of prepared indoles in high yields by base catalyzed reaction with the corresponding alkylating (sulfonylating) reagents. A high synthetic utility of the prepared haloindoles in the reaction with various nucleophilies was shown. The reaction with 4-methylthiophenol and copper cyanide afforded the corresponding sulfides and nitriles in high yield. Palladium catalyzed cross-coupling with phenyl boronic acid and phenylacetylene gave the corresponding 3-phenyl-2-CF<sub>3</sub>-indoles and acetylenic derivatives in 72–98% yield.https://www.mdpi.com/1420-3049/27/24/8822CF<sub>3</sub>-grouphalogenationnucleophilic substitutionindolefluorine |
| spellingShingle | Vasiliy M. Muzalevskiy Zoia A. Sizova Valentine G. Nenajdenko Synthesis and Reactions of 3-Halogenated 2-CF<sub>3</sub>-Indoles Molecules CF<sub>3</sub>-group halogenation nucleophilic substitution indole fluorine |
| title | Synthesis and Reactions of 3-Halogenated 2-CF<sub>3</sub>-Indoles |
| title_full | Synthesis and Reactions of 3-Halogenated 2-CF<sub>3</sub>-Indoles |
| title_fullStr | Synthesis and Reactions of 3-Halogenated 2-CF<sub>3</sub>-Indoles |
| title_full_unstemmed | Synthesis and Reactions of 3-Halogenated 2-CF<sub>3</sub>-Indoles |
| title_short | Synthesis and Reactions of 3-Halogenated 2-CF<sub>3</sub>-Indoles |
| title_sort | synthesis and reactions of 3 halogenated 2 cf sub 3 sub indoles |
| topic | CF<sub>3</sub>-group halogenation nucleophilic substitution indole fluorine |
| url | https://www.mdpi.com/1420-3049/27/24/8822 |
| work_keys_str_mv | AT vasiliymmuzalevskiy synthesisandreactionsof3halogenated2cfsub3subindoles AT zoiaasizova synthesisandreactionsof3halogenated2cfsub3subindoles AT valentinegnenajdenko synthesisandreactionsof3halogenated2cfsub3subindoles |