Abstract
The reaction of naphtho[2,3-a]phenazine-8,13-dlone (I) with hydrogen chloride leads, depending on the solvent, to 2- or 6-ehlorodihydroazines, which are converted to 2,6-dichloro derivatives after oxidation and retreatment with hydrogen chloride; the corresponding 6-amino-substituted naphthophenazinediones are formed by reaction with amines. The direction of nucleophilic attack in these reactions is caused by the coordinated electron-acceptor effect of the peri-oriented oxygen atoms of the quinone grouping and the heterocyclic nitrogen and by intensified protonation with the closing of an intramolecular hydrogen bond.
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Literature cited
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See [7] for communication XXIV.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1139–1144, August, 1971.