Recently, the hexadehydro-Diels-Alder (HDDA) reaction has become a powerful tool for the synthesize of complex organic molecules. We have now discovered a related process, which we have termed the pentadehydro-Diels-Alder (PDDA) reaction. This represents a novel strategy for the synthesis of pyridine derivatives using a [4+2] cycloaddition reaction. For example, piperidine-catalyzed tautomerization of the 1,3-diyne 1 leads to the novel tricylic amine 3, via, we presume, the reactive intermediate 2. It is noteworthy that nitriles are not effective participants in the analogous of HDDA process. Synthetic as well as mechanistic aspects will be presented.

Pentadehydro-Diels-Alder (PDDA) reaction Part 2: Cycloadditions of allenynes with nitriles to give pyridine derivatives

249th National Meeting (2015)

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