The Diels-Alder cycloaddition is one of the most powerful and widely exploited reactions in organic synthesis. This work attempts to develop a tandem 2,3-sigmatropic shift/intramolecular Diels-Alder cycloaddition of 1,2,4-triazines substituted at the 3-position with allyl, propargyl and allenyl sulfoxides. A sulfoxide to sulfenate rearrangement would lengthen the tether by one atom, facilitating intramolecular 4+2 cycloaddition. Extrusion of N2 would afford either directly, or upon oxidation, pyridine products.

Exploration of tandem sulfoxide-sulfenate rearrangement/intramolecular Diels-Alder reactions of 1,2,4-triazines

245th National Meeting (2013)

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