Vinylketenes (generated in situ from cyclobutenones or a-diazo ketones) react with ynamides via a pericyclic cascade process to produce highly-substituted aniline derivatives.  Deprotection followed by iodocyclization then yields products that are highly substituted on both rings of the quinoline nucleus.  This talk will focus on the scope, limitations, and mechanism of this new tandem strategy.

Synthesis of highly substituted quinolines via a tandem ynamide benzannulation/iodocyclization strategy

240th National Meeting (2010)

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