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Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines.

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journal contribution
posted on 15.12.2016 by D Kontokosta, DS Mueller, DL Mo, WH Pace, RA Simpson, LL Anderson
A Chan-Lam reaction has been used to prepare N-alkenyl-α,β-unsaturated nitrones, which undergo a subsequent thermal rearrangement to the corresponding tri- and tetrasubstituted pyridines. The optimization and scope of these transformations is discussed. Initial mechanistic experiments suggest a reaction pathway involving oxygen transfer followed by cyclization.

Funding

We acknowledge generous funding from ACS-PRF (DNI-50491), NSF (NSF-CHE 1212895 and 1464115), and the University of Illinois at Chicago.

History

Publisher Statement

This is a copy of an article published in the Beilstein Journal of Organic Chemistry. © 2015 Beilstein-Institut Publications. © 2015 Kontokosta et al.

Publisher

Beilstein-Institut

Language

en_US

Issue date

04/11/2015

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