REACTIONS OF LUCIGENIN IN PROTIC SOLVENTS IN THE PRESENCE OF AMINES
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DIMOTIKALI, D
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PAPADOPOULOS, K
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NIKOKAVOURAS, J
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Lucigenin (NN'-dimethyl-9,9'-biacridinium nitrate) 1 on heating under reflux in protic solvents in the presence of amines gives rise to the NN'-dimethyl-9,9'-biacridylidene 2 (DBA) or protected hemiaminal N-methoxymethyl-9,9'-biacridylidene 3. On the other hand acid hydrolysis and synchronous oxidation of hemiaminal 3 followed by reaction of monomethyl-biacridinium nitrate 4 with sodium hydroxide in methanol or water leads to biacridine 5 (overall yield ca. 33%).
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