Reactions of HDDA Benzynes with C,N-Diarylimines (ArCH=NAr')

Sahil Arora, Dorian S. Sneddon, Thomas R. Hoye

Research output: Contribution to journalArticle

Abstract

o-Benzynes can be utilized to construct heterocyclic motifs using various nucleophilic and cycloaddition trapping reactions. Acridines have been synthesized by capture of C,N-diarylimines with benzynes generated by classical methods (i.e., from ortho-elimination of precursor arene compounds), although in poor yields. We report here that these imines can be trapped by benzynes generated by the hexadehydro-Diels–Alder (HDDA) reaction in an efficient manner to produce 1,4-dihydroacridine products. These dihydroacridines were subsequently aromatized using MnO2 to provide structurally complex acridines.

Original languageEnglish (US)
JournalEuropean Journal of Organic Chemistry
DOIs
StateAccepted/In press - Jan 1 2020

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Keywords

  • Acridines
  • Azoquinone methides
  • Benzazetidines
  • Dihydroacridines
  • HDDA-benzynes

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