Beilstein J. Org. Chem.2014,10, 921–928, doi:10.3762/bjoc.10.90
protocol has a broad scope for the bromination of various substituted and unsubstituted aminoanthracene-9,10-diones.
Keywords: aminoanthracene-9,10-dione; benzanthrone; KBr; nonanebis(peroxoic acid); oxidative bromination; Introduction
The brominated aminoanthracene-9,10-dione derivatives and
benzanthrone are widely used as intermediates for pharmaceuticals [1][2][3], for medicinal applications [4], as dyes [5][6][7][8][9] and in Hg2+ ion sensors [10]. Although these bromo derivatives have a wide range of applications, it is difficult to carry out their bromination as the two carbonyl groups of
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Graphical Abstract
Scheme 1:
Aliphatic peracid mediated bromination of aminoanthracene-9,10-dinone.
Beilstein J. Org. Chem.2009,5, No. 31, doi:10.3762/bjoc.5.31
Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany 10.3762/bjoc.5.31 Abstract Treatment of benzanthrone (1) with biphenyl-2-yl lithium leads to the surprisingly
stable enol 4, which is converted by dehydrogenation into the benzanthrone derivative 7. Under acidic conditions 4 isomerises to the spiro compound 11 and the bicyclo[4.3.1]decane derivative 12. Furthermore, the formation of 7 and the hydrogenated compound 13 is observed. A mechanism for the formation of
-emitting diodes, OLEDs) or light-harvesting properties (e.g. organic solar cells) are receiving more and more attention [1]. In this respect benzanthrone (1), with its luminescent and photosensitizing properties, is an interesting candidate for the construction of these systems. Recently, aminobenzanthrone
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Graphical Abstract
Scheme 1:
Behaviour of benzanthrone (1) towards phenylmagnesium chloride (a), phenyl lithium (b), and bipheny...