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Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with isoxazoles via novel 6π-electrocyclizations of 3-azahepta trienyl cations
New gold-catalyzed [4+3]-annulations of 3-en-1-ynamides with isoxazoles afford 4H-azepines efficiently; this process involves 6π electrocyclizations of gold-stabilized 3-azaheptatrienyl cations. In the presence of Zn(OTf)(2), the resulting 4H-azepines undergo skeletal rearrangement to furnish substi...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5915799/ https://www.ncbi.nlm.nih.gov/pubmed/29732082 http://dx.doi.org/10.1039/c8sc00232k |
Sumario: | New gold-catalyzed [4+3]-annulations of 3-en-1-ynamides with isoxazoles afford 4H-azepines efficiently; this process involves 6π electrocyclizations of gold-stabilized 3-azaheptatrienyl cations. In the presence of Zn(OTf)(2), the resulting 4H-azepines undergo skeletal rearrangement to furnish substituted pyridine derivatives. We subsequently develop new catalytic [4+2]-annulations between the same 3-en-1-ynamides and isoxazoles to deliver substituted pyridine products using Au(i)/Zn(ii) catalysts. This work reports the first success of the 6π electrocyclizations of heptatrienyl cations that are unprecedented in literature reports. |
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