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Title: | Synthesis and new rearrangements of 4-isoxazolin-4,5-dicarboxylic acid derivatives |
Authors: | Uludağ Üniversitesi/Fen-Edebiyat Fakültesi/Kimya Bölümü. Coşkun, Necdet Öztürk, Aylin 7004177880 15056758100 |
Keywords: | Chemistry Rearrangement Pyrrole derivative Nitrones Dipolar cycloaddition Acyclic azomethine ylides 4-Isoxazolines 1H-Pyrrole-3-carboxylic acid methyl ester Nitrones Regio Reactivity Aryl isocyanates Diastereoselective addition Imidazoline 3-oxides 1,3-dipolar cycloaddition reactions Ring-opening reactions 1-beta-methylcarbapenem |
Issue Date: | 18-Dec-2006 |
Publisher: | Pergamon-Elsevier Science |
Citation: | Coşkun, N. ve Öztürk, A. (2006). ''Synthesis and new rearrangements of 4-isoxazolin-4,5-dicarboxylic acid derivatives''. Tetrahedron, 62(51), 12057-12063. |
Abstract: | Acyclic nitrones react with dimethyl acetylenedicarboxylate (DMAD) to give stable isoxazolines, from which the ones that contain electron-donating aromatic rings at the C3 position (R-1) were shown to undergo unprecedented fragmentation at room temperature, giving the R-1-aldehyde and inseparable product mixtures, probably due to the formation of highly reactive species such as iminocarbenes. Attempts to convert the isoxazolines to the corresponding stable azomethine ylides, by refluxing in toluene, again led to the same product mixtures as above (e.g., the room temperature decomposition). Isoxazolines when reacted with methoxide at room temperature afforded highly function-alised diastereomeric mixtures. Also, isoxazolines, when reacted with propylamine, gave the corresponding amides regioselectively, all of which were more stable than the parent isoxazolines. |
URI: | https://doi.org/10.1016/j.tet.2006.09.074 https://www.sciencedirect.com/science/article/pii/S0040402006015511 http://hdl.handle.net/11452/22898 |
ISSN: | 0040-4020 |
Appears in Collections: | Web of Science |
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