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Ring-chain isomerism and reactions of 2-(1-anthraquinonecarbonyl)-1,2,3,4-tetrahydrophthalazine

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The ring isomer of the corresponding acyl derivative — 5,9-dioxo-17a-hydroxy-9,10,11,16-17,17a-hexahydro-5H-dibenzo[d,e,h]phthalazino[2,3-a]cinnoline — was obtained by acylation of 1,2,3,4-tetrahydrophthalazine with anthraquinone-1-carboxylic acid chloride. Treatment of the product with thionyl chloride or hydrogen chloride gave the deeply colored 5,9-dioxo-9,10,11,16-tetrahydro-5H-dibenzo[d,e,h]phthalazino[2,3-a]cinnolinium chloride. The possibility of charge transfer between the chloride anion and the phthalazinium cation is examined as a reason for the deep coloration. This compound very readily undergoes hydrolytic oxidative cleavage at the C-N bond to give 2-(2-formylbenzyl)-3,7-dioxo-2,3-dihydro-7H-dibenzo[d,e,h]cinnoline.

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Authors and Affiliations

  1. Riga Polytechnic Institute, 226355, Riga

    Ya. R. Mednis, R. É. Valter, V. É. Kampar & O. Ya. Neiland

Authors
  1. Ya. R. Mednis
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  2. R. É. Valter
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  3. V. É. Kampar
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  4. O. Ya. Neiland
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1411–1415, October, 1977.

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Mednis, Y.R., Valter, R.É., Kampar, V.É. et al. Ring-chain isomerism and reactions of 2-(1-anthraquinonecarbonyl)-1,2,3,4-tetrahydrophthalazine. Chem Heterocycl Compd 13, 1133–1136 (1977). https://doi.org/10.1007/BF00480154

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  • DOI: https://doi.org/10.1007/BF00480154

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