Cyclization of propargylic amides: mild access to oxazole derivatives
The substrate scope, the mechanistic aspects of the gold-catalyzed oxazole synthesis, and substrates with different aliphatic, aromatic, and functional groups in the side chain were investigated. Even molecules with several propargyl amide groups could easily be converted, delivering di- and trioxaz...
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| Hauptverfasser: | , , , , , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
[January 18, 2010]
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| In: |
Chemistry - a European journal
Year: 2010, Jahrgang: 16, Heft: 3, Pages: 956-963 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.200902472 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.200902472 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.200902472 
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| Verfasserangaben: | Jan P. Weyrauch, A. Stephen K. Hashmi, Andreas Schuster, Tobias Hengst, Stefanie Schetter, Anna Littmann, Matthias Rudolph, Melissa Hamzic, Jorge Visus, Frank Rominger, Wolfgang Frey, and Jan W. Bats |
MARC
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| 245 | 1 | 0 | |a Cyclization of propargylic amides |b mild access to oxazole derivatives |c Jan P. Weyrauch, A. Stephen K. Hashmi, Andreas Schuster, Tobias Hengst, Stefanie Schetter, Anna Littmann, Matthias Rudolph, Melissa Hamzic, Jorge Visus, Frank Rominger, Wolfgang Frey, and Jan W. Bats |
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| 520 | |a The substrate scope, the mechanistic aspects of the gold-catalyzed oxazole synthesis, and substrates with different aliphatic, aromatic, and functional groups in the side chain were investigated. Even molecules with several propargyl amide groups could easily be converted, delivering di- and trioxazoles with interesting optical properties. Furthermore, the scope of the gold(I)-catalyzed alkylidene synthesis was investigated. Further functionalizations of these isolable intermediates of the oxazole synthesis were developed and chelate ligands can be obtained. The use of Barluenga’s reagent offers a new and mild access to the synthetically valuable iodoalkylideneoxazoles from propargylic amides, this reagent being superior to other sources of halogens. | ||
| 650 | 4 | |a cyclization | |
| 650 | 4 | |a fluorescence | |
| 650 | 4 | |a gold catalysis | |
| 650 | 4 | |a methyleneoxazolines | |
| 650 | 4 | |a oxazoles | |
| 650 | 4 | |a propargylic amides | |
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