Gold-catalysis: highly efficient and regio-selective carbonyl migration in alkynyl-substituted indole-3-carboxamides leading to azepino[3,4-b]indol-1-ones
An unprecedented rearrangement/anellation sequence allows the clean synthesis of azepino[3,4-b]indol-1-ones from readily available starting materials. Alkyne-substituted indole-3-carboxamides were prepared and converted to azepino[3,4-b]indol-1-ones by the SPhosAuNTf2 catalyst (SPhos=2-dicyclohexylp...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
April 24, 2012
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| In: |
Advanced synthesis & catalysis
Year: 2012, Volume: 354, Issue: 7, Pages: 1273-1279 |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201200092 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/adsc.201200092 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201200092 
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| Author Notes: | A. Stephen K. Hashmi, Weibo Yang, and Frank Rominger |
| Summary: | An unprecedented rearrangement/anellation sequence allows the clean synthesis of azepino[3,4-b]indol-1-ones from readily available starting materials. Alkyne-substituted indole-3-carboxamides were prepared and converted to azepino[3,4-b]indol-1-ones by the SPhosAuNTf2 catalyst (SPhos=2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl). The new connectivity, which involves an unprecedented 3,2-shift of an acylamino group for the product formation, was proven by a crystal structure analysis. |
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| Item Description: | Gesehen am 06.09.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201200092 |