Synthesis and intramolecular ring transformation of N,N'-dialkylated 2,6,9-triazabicyclo[3.3.1]nonadienes.

The first and facile synthesis of N,N'-dialkylated 2,6,9-triazabicyclo[3.3.1]nonadienes was achieved by the [4 + 4] self-condensation of β-formyl-β-nitroenamine in the presence of ammonium acetate. The 2,6- and 2,9-dialkylated products were found to be interconvertible when dissolved in a solvent. This isomerization proceeds through intramolecular ring transformation via a common intermediate under equilibrium.