Bimolecular reduction of 9-alkyl-3-nitrocarbazoles |
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Authors: | J B Kyzioł |
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Institution: | (1) Institute of Chemistry, University of Opole, ul. Oleska 48, PL-45 040 Opole, Poland |
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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-dialkyldiindolo3,2-a,d]phenazines (IIIa–IIId) were obtained. Parent compounds, viz. 3,3′-azocarbazole (IIf) and diindolo3,2-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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Keywords: | nitro-to-azo reduction benzidine rearrangement auotoxidation |
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