Fluorinated 2-Azetines: Synthesis, Applications, Biological Tests, and Development of a Catalytic Process.
| Autor: | Losa R; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198, Gif-sur-Yvette, France., Lorton C; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198, Gif-sur-Yvette, France., Retailleau P; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198, Gif-sur-Yvette, France., Bignon J; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198, Gif-sur-Yvette, France., Voituriez A; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198, Gif-sur-Yvette, France. |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2023 Jul 14; Vol. 25 (27), pp. 5140-5144. Date of Electronic Publication: 2023 Jun 30. |
| DOI: | 10.1021/acs.orglett.3c01888 |
| Abstrakt: | An efficient and straightforward phosphine-promoted tandem aza-Michael addition/intramolecular Wittig reaction was developed for the synthesis of polyfunctionalized 2-azetines. After demonstrating that this transformation could be made catalytic in phosphine through in situ reduction of phosphine oxide with phenylsilane, different post-transformation steps have been demonstrated, including an original [2 + 2] photodimerization. Preliminary biological tests highlighted that these fluorinated 1,2-dihydroazete-2,3-dicarboxylates exhibited significant cytotoxicity against the human tumor cell line. |
| Databáze: | MEDLINE |
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