Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination
The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.14.123 |
| _version_ | 1818915064384585728 |
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| author | Jiyun Sun Xiaohua Zhen Huaibin Ge Guangtao Zhang Xuechan An Yunfei Du |
| author_facet | Jiyun Sun Xiaohua Zhen Huaibin Ge Guangtao Zhang Xuechan An Yunfei Du |
| author_sort | Jiyun Sun |
| collection | DOAJ |
| description | The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process. |
| first_indexed | 2024-12-19T23:56:20Z |
| format | Article |
| id | doaj.art-5d55fe3741464b6bbf6642917723c5e5 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T23:56:20Z |
| publishDate | 2018-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-5d55fe3741464b6bbf6642917723c5e52022-12-21T20:01:00ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-06-011411452145810.3762/bjoc.14.1231860-5397-14-123Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirinationJiyun Sun0Xiaohua Zhen1Huaibin Ge2Guangtao Zhang3Xuechan An4Yunfei Du5Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, ChinaTianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, ChinaTianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, ChinaTianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, ChinaTianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, ChinaTianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, ChinaThe reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process.https://doi.org/10.3762/bjoc.14.123azirination2H-azirineiodosobenzeneTogni reagentβ-trifluoromethylation |
| spellingShingle | Jiyun Sun Xiaohua Zhen Huaibin Ge Guangtao Zhang Xuechan An Yunfei Du Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination Beilstein Journal of Organic Chemistry azirination 2H-azirine iodosobenzene Togni reagent β-trifluoromethylation |
| title | Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination |
| title_full | Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination |
| title_fullStr | Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination |
| title_full_unstemmed | Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination |
| title_short | Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination |
| title_sort | synthesis of trifluoromethylated 2h azirines through togni reagent mediated trifluoromethylation followed by phio mediated azirination |
| topic | azirination 2H-azirine iodosobenzene Togni reagent β-trifluoromethylation |
| url | https://doi.org/10.3762/bjoc.14.123 |
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