"An Unexpected Synthesis of Dihydrophenazines en Route to Benzimidazolium Salts"

Yannick Borguet, Guillermo Zaragoza, Albert Demonceau, and Lionel Delaude

Journal Cover
          source: Advanced Synthesis & Catalysis
            year: 2012
          volume: 354
      first page: 1356
       last page: 1362
             doi: 10.102/adsc.201100890

graphical abstract

Abstract: The oxidation of various N,N'-diarylbenzene-1,2-diamines bearing bulky aromatic substituents with sodium periodate on wet silica gel afforded a series of five new dihydrophenazines instead of the expected cyclohexadiene-1,2-diimines. The reaction most likely proceeds via a 1,6-electrocyclic path and provides a convenient access to an important class of nitrogen heterocycles. Subsequent treatment of the mesityl derivative with chloromethyl pivalate and silver triflate led to the corresponding benzimidazolium salt.

Keywords: Electrocyclic Reactions, Ligand Design, Nitrogen Heterocycles, Oxidation, Sigmatropic Rearrangement

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