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Issue 11, 2018
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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

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Abstract

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.

Graphical abstract: Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with isoxazoles via novel 6π-electrocyclizations of 3-azahepta trienyl cations

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Publication details

The article was received on 15 Jan 2018, accepted on 18 Feb 2018 and first published on 19 Feb 2018


Article type: Edge Article
DOI: 10.1039/C8SC00232K
Chem. Sci., 2018,9, 2991-2995
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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

    S. S. Giri and R. Liu, Chem. Sci., 2018, 9, 2991
    DOI: 10.1039/C8SC00232K

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