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C–C recyclizations of some 2,7-disubstituted 6-ethoxycarbonylpyrazolo[1,5-a]pyrimidines

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Chemistry of Heterocyclic Compounds Aims and scope

Condensation of ethyl ethoxymethyleneacetoacetate and ethyl ethoxymethylenecyanoacetate in ethanol with 3-substituted 3-aminopyrazoles and 5-amino-1,2,4-triazole gave the 2-substituted 6-ethoxy- carbonyl-7-methyl- and 7-amino-6-ethoxycarbonylpyrazolo[1,5-a]pyrimidines as well as 7-amino-6-ethoxycarbonyl-1,2,4-triazolo[1,5-a]pyrimidine. In the presence of alkali these rearranged to 2-substituted 6-acetyl-7-hydroxy- and 6-carbamoyl-7-hydroxypyrazolo[1,5-a]pyrimidines respectively and also to 6-carbamoyl-7-hydroxy-1,2,4-triazolo[1,5-a]pyrimidine. According to 1H (including NOESY) NMR spectroscopic data there were formed, along with the cyclization products, noncyclic condensation adducts (as cyano derivatives) from ethyl ethoxymethylenecyanoacetate with 5-aminopyrazoles. In the presence of alcoholic alkaline solution these were also transformed in high yield to 6-carbamoyl-7-hydroxypyrazolopyrimidines. When refluxed for a longer time in 12% aqueous alcoholic alkaline solution the 6-ethoxycarbonyl-2,7-dimethylpyrazolo[1,5-a]pyrimidine and 6-acetyl-7-hydroxy-2-methylpyrazolo[1,5-a]pyrimidine recyclize to give 6-carboxy-2,7-dimethyl- and 2,7-di- methylpyrazolo[1,5-a]pyrimidines.

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Authors and Affiliations

  1. Russian-Armenian (Slavonic) State University, 123 Hovsep Emin St., Yerevan, 0091, Republic of Armenia

    G. G. Danagulyan

  2. Institute of Organic Chemistry, Scientific-Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 167-A Zakariya Kanakertsi St., Yerevan, 0094, Republic of Armenia

    G. G. Danagulyan, A. P. Boyakhchyan & A. G. Danagulyan

  3. Molecular Structure Research Center, Scientific-Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatunyan Ave, Yerevan, 0014, Republic of Armenia

    H. A. Panosyan

Authors
  1. G. G. Danagulyan
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  2. A. P. Boyakhchyan
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  3. A. G. Danagulyan
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  4. H. A. Panosyan
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Correspondence to G. G. Danagulyan.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 393–405, March, 2011.

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Danagulyan, G.G., Boyakhchyan, A.P., Danagulyan, A.G. et al. C–C recyclizations of some 2,7-disubstituted 6-ethoxycarbonylpyrazolo[1,5-a]pyrimidines. Chem Heterocycl Comp 47, 321–331 (2011). https://doi.org/10.1007/s10593-011-0760-x

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  • DOI: https://doi.org/10.1007/s10593-011-0760-x

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