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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4660996PMC
http://dx.doi.org/10.3762/bjoc.11.226DOI Listing

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