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

Org Biomol Chem

School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan. and Research Center for Molecular Design, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.

Published: November 2020

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.

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http://dx.doi.org/10.1039/d0ob01950jDOI Listing

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