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Diazocarbonyl derivatives of heterocycles. 6. Intramolecular reactions of 2-carbomethoxy-3-diazoacetylquinoline

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Treatment of 2-carbomethoxy-3-diazoacetylquinoline with mineral acids results in an intramolecular reaction leading to the formation of 6H-2,5-dioxopyrano-[3,4-b]quinoline; in the presence of bases the intramolecular condensation product is 2-diazo-1,3-dioxocyclopenteno[4,5-b]-quinoline. Treatment of 2-carbomethoxy-3-diazoacetylquinoline with sodium methoxide results in a reversible intramolecular rearrangement via migration of the diazomethine fragment and formation of the isomeric 3-carbomethoxy-2-diazoacetylquinoline.

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Authors and Affiliations

  1. Branch of the Institute of Chemical Physics, Academy of Sciences of the USSR, 142432, Chernogolovka

    S. V. Chapishev & V. G. Kartsev

Authors
  1. S. V. Chapishev
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  2. V. G. Kartsev
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Additional information

For communication No. 5 see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 959–962, July, 1987.

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Chapishev, S.V., Kartsev, V.G. Diazocarbonyl derivatives of heterocycles. 6. Intramolecular reactions of 2-carbomethoxy-3-diazoacetylquinoline. Chem Heterocycl Compd 23, 787–789 (1987). https://doi.org/10.1007/BF00475652

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  • DOI: https://doi.org/10.1007/BF00475652

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