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Reinvestigation of the Synthesis of Hydroxy‐Functionalized Diazapentacene: Unexpected Formation of a Phenoxazinone
Author(s) -
Müller Lisa,
Hübner Eike G.,
Burzlaff Nicolai
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701115
Subject(s) - phenoxazine , chemistry , reagent , derivative (finance) , fluorescence , stereochemistry , single crystal , combinatorial chemistry , medicinal chemistry , organic chemistry , crystallography , medicine , physics , quantum mechanics , phenothiazine , financial economics , economics , pharmacology
In 1982, Buckley et al. reported on the hydroxy‐functionalized derivative of 6,13‐diazapentacene (DAP), namely 5,12‐dihydroxo‐6,13‐diazapentacene. In an attempt to reproduce the synthetic procedure, 1 H NMR and 13 C{ 1 H} NMR spectroscopic data revealed the formation of a constitutional isomer of the supposed compound. A single‐crystal X‐ray structure determination revealed that the actual structure of the dark‐violet product was 6‐amino‐5 H ‐dibenzo[ a , h ]phenoxazin‐5‐one ( 2 ), a benzo[ a ]phenoxazine derivative. These kinds of compounds are, along with a wide range of pharmacological applications, known for their specific fluorescent properties, which were analyzed for compound 2 . Furthermore, it was shown that 2 can be utilized as reagent for the synthesis of other benzo[ a ]phenoxazine derivatives, herein 6‐(dimethylamino)‐5 H ‐dibenzo[ a , h ]phenoxazin‐5‐one ( 3 ).