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Efficient synthesis of multisubstituted 2-alkenylpyridines via 2,3-rearrangement of O-homoallenylic oximes

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Abstract

O-Homoallenylic α,β-unsaturated oximes were efficiently converted to the corresponding 2-alkenylpyridine derivatives by microwave irradiation. The present reaction proceeds via 2,3-rearrangement followed by 6π-electrocyclization of the resulting N-(2-dienyl)nitrone intermediate serving as a 3-azatriene.

Graphical abstract: Efficient synthesis of multisubstituted 2-alkenylpyridines via 2,3-rearrangement of O-homoallenylic oximes

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Publication details

The article was received on 10 Nov 2016, accepted on 08 Feb 2017 and first published on 09 Feb 2017


Article type: Research Article
DOI: 10.1039/C6QO00703A
Citation: Org. Chem. Front., 2017, Advance Article
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    Efficient synthesis of multisubstituted 2-alkenylpyridines via 2,3-rearrangement of O-homoallenylic oximes

    I. Nakamura, Y. Oyama, D. Zhang and M. Terada, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C6QO00703A

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