Bimolecular reduction of 9-alkyl-3-nitrocarbazoles

  • 1 Institute of Chemistry, University of Opole, ul. Oleska 48, PL-45 040, Opole, Poland

Abstract

Reduction of 9-alkyl-3-nitrocarbazoles (Ia–Ie) with lithium aluminium hydride gave corresponding 9,9′-dialkyl-3,3′-azocarbazoles (IIa–IIe) in moderate yield. By the action of zinc dust in alcohol and aqueous alkali on I or II, 5,13-dialkyldiindolo[3,2-a,d]phenazines (IIIa–IIId) were obtained. Parent compounds, viz. 3,3′-azocarbazole (IIf) and diindolo[3,2-a,d]phenazine (IIIf) could not be obtained in these ways. Compound IIf was obtained in Vorländer reaction and IIIf by thermal decomposition of 3-azidocarbazole. Formation of IIIa–IIId is explained as a result of ortho-benzidine rearrangement of hypothetical 9,9′-dialkyl-3,3′-hydrazocarbazoles.

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