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Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts

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Chemistry of Heterocyclic Compounds Aims and scope

We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of N-azolyl- and С-pyrazolylsubstituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and formation of ethyl 2-(pyrazolylalkyl)- and 2-(azolylalkyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5-a]pyrimidine.

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This work was performed within the framework of Russian-Armenian grant 13RF-087 by the State Committee for Science at the Ministry of Education and Science, Republic of Armenia and the Russian Foundation for Basic Research, as well as with financial support from the State Committee for Science at the Ministry of Education and Science, Republic of Armenia (grant 13-1D334).

NMR spectra were acquired at the Molecular Structure Research Center, National Academy of Sciences of the Republic of Armenia (program US CRDF RESC 17–5).

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Authors and Affiliations

  1. Russian-Armenian (Slavonic) University, 123 Hovsep Emin St., Yerevan, 0051, Armenia

    Gevorg G. Danagulyan, Araksya K. Tumanyan & Anna G. Danagulyan

  2. Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan, 0014, Armenia

    Gevorg G. Danagulyan, Araksya K. Tumanyan, Oganes S. Attaryan & Anna G. Danagulyan

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

    Rafael A. Tamazyan & Armen G. Ayvazyan

Authors
  1. Gevorg G. Danagulyan
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  2. Araksya K. Tumanyan
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  3. Oganes S. Attaryan
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  4. Rafael A. Tamazyan
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  5. Anna G. Danagulyan
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  6. Armen G. Ayvazyan
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Correspondence to Gevorg G. Danagulyan.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(5), 483–490

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Danagulyan, G.G., Tumanyan, A.K., Attaryan, O.S. et al. Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts. Chem Heterocycl Comp 51, 483–490 (2015). https://doi.org/10.1007/s10593-015-1724-3

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  • DOI: https://doi.org/10.1007/s10593-015-1724-3

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