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Reaction of Β-oxonitrones — Imidazoline and pyrroline derivatives — With nucleophilic reagents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of Β-oxonitrones — imidazoline derivatives — with hydroxylamine, phenylhydrazine, and semicarbazide takes place at the carbonyl group with retention of the nitrone group. Stable nitroxyl radicals — spiroimidazoisoxazole derivatives — are formed in the oxidation of Β-hydroximinonitrones. The recyclization of the Β-oxonitrones, which takes place in an acidic medium, as well as by the action of hydrazine and thiosemicarbazide, leads, respectively, to pyrroline and pyrazole derivatives.

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Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, 630090, Novosibirsk

    V. A. Reznikov & L. B. Volodarskii

Authors
  1. V. A. Reznikov
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  2. L. B. Volodarskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 912–919, July, 1991.

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Reznikov, V.A., Volodarskii, L.B. Reaction of Β-oxonitrones — Imidazoline and pyrroline derivatives — With nucleophilic reagents. Chem Heterocycl Compd 27, 722–728 (1991). https://doi.org/10.1007/BF00476201

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  • DOI: https://doi.org/10.1007/BF00476201

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