2-Amino-4,4α-dihydro-4α,7-dimethyl-3H-phenoxazin-3-one as an unexpected product from reduction of 5-methyl-2-nitrophenol
Publication date
2015-02-25
Authors
Jansze, Suzanne M.
Saggiomo, Vittorio
Marcelis, Antonius T M
Lutz, Martin
Velders, Aldrik H.
Editors
Advisors
Supervisors
Document Type
Article
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taverne
Abstract
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-4,4α-dihydro-4α,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.
Keywords
Taverne, Biochemistry, Organic Chemistry, Drug Discovery
Citation
Jansze, S M, Saggiomo, V, Marcelis, A T M, Lutz, M & Velders, A H 2015, '2-Amino-4,4α-dihydro-4α,7-dimethyl-3H-phenoxazin-3-one as an unexpected product from reduction of 5-methyl-2-nitrophenol', Tetrahedron Letters, vol. 56, no. 9, pp. 1060-1062. https://doi.org/10.1016/j.tetlet.2015.01.089