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Ring-chain isomerization of 2-substituted 3-hydroxy-3-(4-dimethyl-aminophenyl)isoindolinones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

N-Unsubstituted and N-monosubstituted amides of 2-(4-dimethylaminobenzoyl)benzole acid exist in the chain form of 3-hydroxyisoindolinones in the crystalline state and in solutions in dioxane, whereas the tautomeric amide ⇄ hydroxyisoindolinone equilibrium occurs (except for the methyl derivative) in more polar solvents. The analogous N-(1-adamantanyl)amide exists in the open form and does not undergo cyclization under alkaline catalysis conditions; protonation of the dimethylamino group is accompanied in all cases by splitting out of water to give compounds with a quinoid structure; an equilibrium between the protonated and quinoid forms, which is shifted markedly to favor the latter, is observed for some compounds.

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Authors and Affiliations

  1. Riga Polytechnic Institute, 226355, Riga

    G. A. Karlivan, R. É. Valter, R. B. Kampare & V. P. Tsiekure

Authors
  1. G. A. Karlivan
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  2. R. É. Valter
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  3. R. B. Kampare
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  4. V. P. Tsiekure
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 780–785, June, 1979.

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Karlivan, G.A., Valter, R.É., Kampare, R.B. et al. Ring-chain isomerization of 2-substituted 3-hydroxy-3-(4-dimethyl-aminophenyl)isoindolinones. Chem Heterocycl Compd 15, 634–639 (1979). https://doi.org/10.1007/BF00539498

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  • DOI: https://doi.org/10.1007/BF00539498

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