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Transformations of 1-amino-2-(3-hydroxyalk-1-ynyl)-9,10-anthraquinones in the presence of amines



When heated in piperidine, 1-amino-2-(3-hydroxyalk-1-ynyl)-9,10-anthraquinones undergo cyclization into 2-(1-hydroxyalkyl)naphtho(2,3- g )indole-6,11-diones. In contrast, 1-amino-2-(3-hydroxy-3-phenylpropynyl)-9,10-anthraquinone reacts with primary and secondary amines to give the corresponding 1-amino-2-(1-amino-2-benzoylvinyl)-9,10-anthraquinones, which undergo cyclization into 4-dialkylamino- or 4-alkylamino-2-phenylnaphtho(2,3- h )quinoline-7,12-diones. Heating of the starting phenylpropynol with Et 3 N causes its dehydrogenation and isomerization.



Russian Chemical BulletinSpringer Journals

Published: Sep 1, 2001

DOI: 10.1023/A:1013055106499

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