Isomeric ellipticines. Part 1. Synthesis of two linear isomers of the antitumour alkaloid ellipticine
| Autor: | Serge Fermandjian, Said El Antri, Adolfo Ricci, P. Jacquignon, Elie Lescot, Alain Deroussent, Pierluigi Orvietani, G. Alunni-Bistocchi, Olivier Mauffret |
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| Rok vydání: | 1992 |
| Předmět: | |
| Zdroj: | Journal of the Chemical Society, Perkin Transactions 1. :2935 |
| ISSN: | 1364-5463 0300-922X |
| DOI: | 10.1039/p19920002935 |
| Popis: | Two linear isomers of the parent 5,11-dimethyl-6H-pyrido[4,3-b]carbazole ellipticine 1a, belonging to the 6H- and 10H-pyridocarbazoles series and their methoxylated derivatives, have been synthesized by three different methods using the Skraup reaction and the Fischer–Borsche cyclization. One of these (method A) afforded an angular monomethyl-7H-pyridocarbazole 9 instead of the expected linear 6H-isomer 8a on cyclisation of 5,8-dimethyl-6-hydrazinoquinoline 21 with cyclo-hexanone via the Fischer–Borsche indole synthesis. The two other methods (B and C) afforded the desired linear isomers 7 and 8 when the Skraup reaction was performed with aminocarbazoles 26 or with tetrahydroaminocarbazoles 17 and 27 respectively, followed by aromatization of the A ring. Oxidized species were isolated after the aromatization step in method C and were tentatively assigned structures 30–33. |
| Databáze: | OpenAIRE |
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