Abstract
The possibility of transformation of 3-cyano-1-p-nitrophenyl-δ-carbolin-2-one into 2-amino-3-cyano-1-p-nitrophenyl-1H-pyrido[3,2-b]indole derivatives and 2-imino-3-cyano-1-p-nitrophenyl-5H-pyrido[3,2-b]indole derivatives (δ-carbolines) is demonstrated. Methylation of 1-p-nitrophenyl-2-piperidino-1H-δ-carboline followed by treatment with acetone in an alkaline medium yields 4-acetonyl-5-methyl-1,4-dihydro-5H-pyrido[3,2-b]indole derivative. The rearrangement of 2-arylimino-3-cyano-1-p-nitrophenyl-5H-pyrido[3,2-b]indoles into 2-(aryl)nitrophenylamino-3-cyano-5H-pyrido[3,2-b]indoles was accomplished on heating above the melting point or on treatment with potassium tert-butoxide. The structures of the resulting compounds were proved by 1H and 13C NMR spectroscopy and X-ray diffraction analysis.
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Ryabova, S.Y., Alekseeva, L.M., Lisitza, E.A. et al. New approach to the functionalization of δ-carboline derivatives. Russian Chemical Bulletin 50, 1449–1456 (2001). https://doi.org/10.1023/A:1012749426699
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DOI: https://doi.org/10.1023/A:1012749426699