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Catalytic claisen amino rearrangement of N-(cyclo)alkenylarylamines and intramolecular cyclization of ortho-alkenylarylamines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Aromatic Claisenamino rearrangements of N-alkenyl-2-methylindoline under the action of Lewis acids leads to 7-alkenyl-2-methylindolines in high yield. Cyclization of ortho-alkenyl compounds was effected in polyphosphoric acid (PPA) and by UV irradiation. Heating 7-(1-methyl-2-butenyl)-2-methylindoline in PPA is accompanied by 1,3-methyl shift in the alkenyl substituent with subsequent cyclization at the aromatic nucleus.

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Authors and Affiliations

  1. Institute of Chemistry of the Bashkir Science Center, Urals Branch, Russian Academy of Sciences, 450054, Ufa

    A. G. Mustafin, I. N. Khalilov, E. V. Tal'vinskii, I. B. Abdrakhmanov & G. A. Tolstikov

  2. Bashkir Agricultural Institute, 450000, Ufa

    A. G. Mustafin, I. N. Khalilov, E. V. Tal'vinskii, I. B. Abdrakhmanov & G. A. Tolstikov

Authors
  1. A. G. Mustafin
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  2. I. N. Khalilov
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  3. E. V. Tal'vinskii
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  4. I. B. Abdrakhmanov
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  5. G. A. Tolstikov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1342–1346, October, 1992.

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Mustafin, A.G., Khalilov, I.N., Tal'vinskii, E.V. et al. Catalytic claisen amino rearrangement of N-(cyclo)alkenylarylamines and intramolecular cyclization of ortho-alkenylarylamines. Chem Heterocycl Compd 28, 1141–1144 (1992). https://doi.org/10.1007/BF00529575

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  • DOI: https://doi.org/10.1007/BF00529575

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