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Aromatic amino-claisen rearrangement in the synthesis of ellipticine

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Abstract

A convenient route is described for the preparation of 1,4-dimethylcarbazole — the key compound in the synthesis of the antitumoral alkaloid ellipticine. The interaction of 2,5-xylidine with 3-chlorocyclohexene led to N-(cyclohex-2-enyl)-2,5-xylidine (I), the two-hour heating of which at 140–150°C gave the product of an amino-Claisen rearrangement, 6-(cyclohex-2-enyl)-2,5-xylidine (II) with a yield of 82%. The intramolecular cyclization of compound (II) in polyphosphoric acid (130–140°C, 5 h) led to 5,6,7,8,12,13-hexahydro-1,4-dimethylcarbazole (III) in a yield of 75%. The dehydrogenation of substance (III) by boiling in trimethylbenzene in the presence of Pd/C gave 1,4-dimethylcarbazole (IV) with a yield of 87%. The conditions for performing the reactions and the physicochemical constants of the compounds obtained are given.

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Authors
  1. A. G. Mustafin
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  2. I. N. Khalilov
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  3. I. B. Abdakhmanov
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  4. G. A. Tolstikov
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Additional information

Institute of Chemistry, Bashkir Scientific Center, Urals Branch, USSR Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, Vol. 6, pp. 816–818, November–December, 1989.

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Mustafin, A.G., Khalilov, I.N., Abdakhmanov, I.B. et al. Aromatic amino-claisen rearrangement in the synthesis of ellipticine. Chem Nat Compd 25, 693–695 (1989). https://doi.org/10.1007/BF00598268

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  • DOI: https://doi.org/10.1007/BF00598268

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