2-Amino-4,4a-dihydro-4a,7-dimethyl-3H-phenoxazin-3-one as an unexpected product from reduction of 5-methyl-2-nitrophenol

S.M. Jansze, V. Saggiomo, A.T.M. Marcelis, M. Lutz, A.H. Velders

Research output: Contribution to journalArticleAcademicpeer-review

3 Citations (Scopus)


When attempting to synthesize symmetric 2,2'-dihydroxy-4,4'-dimethyl-azobenzene from 5-methyl-2-nitrophenol by reductive methods based on two literature procedures, an unexpected product was isolated in 30% yield. Full analysis by mass spectrometry, NMR spectroscopy, and single-crystal X-ray structure analysis, proved this product to be tricyclic 2-amino-4,4a-dihydro-4a,7-dimethyl-3H-phenoxazin-3-one. This Letter conveys a warning regarding reductive synthetic routes toward azobenzenes. We also present a novel reductive synthetic route for phenoxazines, an important class of tricyclic compounds.
Original languageEnglish
Pages (from-to)1060-1062
JournalTetrahedron Letters
Issue number9
Publication statusPublished - 2015


  • aromatic nitro-compounds
  • phenoxazinone synthase
  • azo-compounds
  • aminophenol
  • mechanism
  • cells

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