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Condensation of 1,2-hydroxylaminooximes with acetylacetone. Conversion of tetrahydroimidazo[1,2-b]isoxazoles into derivatives of 2H-imidazole, 1-hydroxypyrrole, and 4-oxotetrahydropyridine

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Abstract

Reaction of 1,2-hydroxylaminooximes with acetylacetone gives tetrahydroimidazo[1,2-b]isoxazoles. 4-Phenyltetrahydroimidazo[1,2-b]isoxazole in methanolic HCl forms the corresponding 2-acetonyl-2H-imidazole. Both tetrahydroimidazo[1,2-b]isoxazoles and 2-acetonyl-2H-imidazole on heating in aqueous KOH convert into 4-oxo-1,2,3,4-tetrahydropyridines along with 3-acetyl-1-hydroxypyrroles.

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Authors and Affiliations

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

    L. N. Grigor'eva, A. Ya. Tikhonov, V. V. Martin & L. B. Volodarskii

  2. Lenin Komsomol Novosibirsk State University, 630090, Novosibirsk

    L. N. Grigor'eva, A. Ya. Tikhonov, V. V. Martin & L. B. Volodarskii

Authors
  1. L. N. Grigor'eva
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  2. A. Ya. Tikhonov
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  3. V. V. Martin
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  4. L. B. Volodarskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 765–771, June, 1990.

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Grigor'eva, L.N., Tikhonov, A.Y., Martin, V.V. et al. Condensation of 1,2-hydroxylaminooximes with acetylacetone. Conversion of tetrahydroimidazo[1,2-b]isoxazoles into derivatives of 2H-imidazole, 1-hydroxypyrrole, and 4-oxotetrahydropyridine. Chem Heterocycl Compd 26, 637–642 (1990). https://doi.org/10.1007/BF00756414

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  • DOI: https://doi.org/10.1007/BF00756414

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