Nitrones as trapping reagents of α,β-unsaturated carbene intermediates - (1,2)Oxazino (5,4-b)indoles by a platinum-catalyzed intermolecular (3+3) cycloaddition
Some readily available Boc-protected 2-(3-methoxy-1-propynyl)anilines and nitrones in platinum-catalyzed reactions deliver [1,2]oxazino[5,4-b]indoles. Twelve examples with yields of 41-95% are reported. Different substituents like nitro, trifluoromethyl, fluoro, bromo, and ester groups are tolerated...
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| Hauptverfasser: | , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
17 May 2013
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| In: |
Advanced synthesis & catalysis
Year: 2013, Jahrgang: 355, Heft: 8, Pages: 1523-1528 |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201300338 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/adsc.201300338 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201300338 
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| Verfasserangaben: | Weibo Yang, Tao Wang, Yang Yu, Shuai Shi, Tuo Zhang, and A. Stephen K. Hashmi |
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| 520 | |a Some readily available Boc-protected 2-(3-methoxy-1-propynyl)anilines and nitrones in platinum-catalyzed reactions deliver [1,2]oxazino[5,4-b]indoles. Twelve examples with yields of 41-95% are reported. Different substituents like nitro, trifluoromethyl, fluoro, bromo, and ester groups are tolerated. With regard to the mechanism, this reaction probably combines an initial intramolecular cyclization/elimination to vinylcarbenoid species and a subsequent stepwise intermolecular [3+3] cycloaddition with the nitrones. | ||
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