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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

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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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Bibliographic Details
Main Authors: Yang, Weibo (Author) , Wang, Tao (Author) , Shi, Shuai (Author) , Zhang, Tuo (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 17 May 2013
In: Advanced synthesis & catalysis
Year: 2013, Volume: 355, Issue: 8, Pages: 1523-1528
ISSN:1615-4169
DOI:10.1002/adsc.201300338
Online Access: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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Author Notes:Weibo Yang, Tao Wang, Yang Yu, Shuai Shi, Tuo Zhang, and A. Stephen K. Hashmi
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Summary: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.
Item Description:Gesehen am 23.07.2021
Im Titel sind die Ausdrücke "1,2", "5,4-b" und "3+3" eckig geklammert
Physical Description:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.201300338

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