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Recyclization of Condensed Carbethoxypyrimidines Accompanied by Substitution of a Carbon Atom into the Heterocycle

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Condensation in ethanol of ethyl ethoxymethyleneacetoacetate with systems containing an amidine fragment (substituted 3-aminopyrazoles and 3-amino-1,2,4-triazole) gave 6-carbethoxy-7-methylpyrazolo[1,5-a]pyrimidines. Addition of base to solutions of the obtained bicyclic carbethoxy derivatives in the course of several minutes caused rearrangement to 6-acetyl-7-hydroxypyrazolo[1,5-a]pyrimidine and 6-acetyl-7-hydroxy-1,2,4-triazolo[1,5-a]pyrimidine respectively. A more prolonged refluxing in 15% aqueous alcohol solution of base caused 6-carbethoxy-7-methyl-2-phenylpyrazolo[1,5-a]pyrimidine and 6-acetyl-7-hydroxy-2-phenylpyrazolo[1,5-a]pyrimidine to recyclize to 7-methylpyrazolo[1,5-a]pyrimidine.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan, 375094, Armenia

    G. G. Danagulyan & A. D. Mkrtchyan

  2. Molecular Structure Research Center, National Academy of Sciences of the Republic of Armenia, Yerevan, 375014, Armenia

    G. A. Panosyan

Authors
  1. G. G. Danagulyan
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  2. A. D. Mkrtchyan
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  3. G. A. Panosyan
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 569–576, April, 2005.

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Danagulyan, G.G., Mkrtchyan, A.D. & Panosyan, G.A. Recyclization of Condensed Carbethoxypyrimidines Accompanied by Substitution of a Carbon Atom into the Heterocycle. Chem Heterocycl Compd 41, 485–491 (2005). https://doi.org/10.1007/s10593-005-0176-6

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  • DOI: https://doi.org/10.1007/s10593-005-0176-6

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