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Pyrroles from ketoximes and acetylene. 22. Dihaloethanes in place of acetylene in reactions with cyclohexanone oxime

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

4,5,6,7-Tetrahydroindole and its 1-vinyl derivative were obtained in overall yields of 30–60% by the reaction of cyclohexanone oxime with 1,2-dichloro- and 1,2-dibromoethane in the MOH-dimethyl sulfoxide (DMSO) superbase system (M = K, Na, Li). Nucleophilic substitution of the halogen in the dihaloethanes by the oximate anion to give the corresponding ethylene glycol bis (imido ether) is a side reaction. The effect of the reaction conditions on the yields of products and the selectivity of the process was examined.

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, 664033, Irkutsk

    A. I. Mikhaleva, B. A. Trofimov, A. N. Vasil'ev, G. A. Komarova & V. I. Skorobogatova

Authors
  1. A. I. Mikhaleva
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  2. B. A. Trofimov
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  3. A. N. Vasil'ev
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  4. G. A. Komarova
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  5. V. I. Skorobogatova
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Additional information

See [1] for communication 21.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1202–1204, September, 1982.

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Mikhaleva, A.I., Trofimov, B.A., Vasil'ev, A.N. et al. Pyrroles from ketoximes and acetylene. 22. Dihaloethanes in place of acetylene in reactions with cyclohexanone oxime. Chem Heterocycl Compd 18, 920–923 (1982). https://doi.org/10.1007/BF00513432

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  • DOI: https://doi.org/10.1007/BF00513432

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