Issue 6, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
10 Nov 2016
Accepted
08 Feb 2017
First published
09 Feb 2017

Org. Chem. Front., 2017,4, 1034-1036

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, 4, 1034 DOI: 10.1039/C6QO00703A

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