Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 488536
Title 2-Amino-4,4a-dihydro-4a,7-dimethyl-3H-phenoxazin-3-one as an unexpected product from reduction of 5-methyl-2-nitrophenol
Author(s) Jansze, S.M.; Saggiomo, V.; Marcelis, A.T.M.; Lutz, M.; Velders, A.H.
Source Tetrahedron Letters 56 (2015)9. - ISSN 0040-4039 - p. 1060 - 1062.
DOI https://doi.org/10.1016/j.tetlet.2015.01.089
Department(s) Organic Chemistry
BioNanoTechnology
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2015
Keyword(s) aromatic nitro-compounds - phenoxazinone synthase - azo-compounds - aminophenol - mechanism - cells
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-4,4a-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.
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