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

doi:10.1016/j.tetlet.2015.01.089

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 journal › Article › Academic › peer-review

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1060-1062
Journal	Tetrahedron Letters
Volume	56
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.089
Publication status	Published - 2015

Keywords

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

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@article{d92290c4bdd74792bbe40eb60369cefd,

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

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.",

keywords = "aromatic nitro-compounds, phenoxazinone synthase, azo-compounds, aminophenol, mechanism, cells",

author = "S.M. Jansze and V. Saggiomo and A.T.M. Marcelis and M. Lutz and A.H. Velders",

year = "2015",

doi = "10.1016/j.tetlet.2015.01.089",

language = "English",

volume = "56",

pages = "1060--1062",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "9",

}

TY - JOUR

T1 - 2-Amino-4,4a-dihydro-4a,7-dimethyl-3H-phenoxazin-3-one as an unexpected product from reduction of 5-methyl-2-nitrophenol

AU - Jansze, S.M.

AU - Saggiomo, V.

AU - Marcelis, A.T.M.

AU - Lutz, M.

AU - Velders, A.H.

PY - 2015

Y1 - 2015

N2 - 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.

AB - 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.

KW - aromatic nitro-compounds

KW - phenoxazinone synthase

KW - azo-compounds

KW - aminophenol

KW - mechanism

KW - cells

U2 - 10.1016/j.tetlet.2015.01.089

DO - 10.1016/j.tetlet.2015.01.089

M3 - Article

VL - 56

SP - 1060

EP - 1062

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 9

ER -