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Regioselectivity of Alkylation of Azolo[1,5-a]pyrimidines

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Abstract

The reactions of substituted 5-aminopyrazoles and 5-amino-1,2,4-triazole with 3-(ethoxymethylidene)acetylacetone, as well as with ethyl acetylpyruvate sodium salt, were employed to synthesize a number of substituted pyrazolo[1,5-a]- and 1,2,4-triazolo[1,5-a]pyrimidines. The alkylation of the synthesized pyrazolo[1,5-a]- and 1,2,4-triazolo[1,5-a]pyrimidines with methyl iodide and ethyl iodide was studied. Evidence was obtained from the NMR (NOESY) spectra that pyrazolo[1,5-a]pyrimidines are alkylated at the nitrogen atom of the pyrimidine ring, while the alkylation of 1,2,4-triazolo[1,5-a]pyrimidines involves the triazole N3 atom.

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REFERENCES

  1. Khudina, O.G., Burgart, Ya.V., and Saloutin, V.I., Russ. J. Org. Chem., 2017, vol. 53, p. 1556. https://doi.org/10.1134/S1070428017100116

    Article  CAS  Google Scholar 

  2. Kobayashi, R., Shibutani, S., Nagao, K., Ikeda, Z., Wang, J., Ibáñez, J., Reynolds, M., Sasaki, Y., and Ohmiya, H., Org. Lett., 2021, vol. 23, p. 5415. https://doi.org/10.1039/D1DT03652A

    Article  CAS  Google Scholar 

  3. Pozharskii, A.F., Teoreticheskie osnovy khimii geterotsiklov (Theoretical Foundations of the Chemistry of Heterocycles), Moscow: Khimiya, 1985.

  4. Danagulyan, G.G., Boyakhchyan, A.P., Danagulyan, A.G., and Panosyan, H.A., Chem. Heterocycl. Compd., 2011, vol. 47, p. 321. https://doi.org/10.1007/s10593-011-0760-x

    Article  CAS  Google Scholar 

  5. Danagulyan, G.G., Boyakhchyan, A.P., Tumanyan, A.K., Danagulyan, A.G., and Araqelyan, M.R., Chem. J. Armenia, 2020, vol. 73, p. 349.

    CAS  Google Scholar 

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Funding

The study was carried out at the Russian-Armenian University (RAU) for funds allocated by the Russian Ministry of Education and Science for research at the RAU, as well as with the financial support of the State Committee for Science of the Republic of Armenia and the Russian Foundation for Basic Research (project no. 20RF-138/20-53-05010 Arm_a/).

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Authors and Affiliations

  1. Russian-Armenian University, 0051, Yerevan, Armenia

    G. G. Danagulyan & V. K. Gharibyan

  2. Scientific and Technological Center for Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, Armenia

    G. G. Danagulyan

  3. St. Petersburg State Institute of Technology, 190013, St. Petersburg, Russia

    V. A. Ostrovskii

Authors
  1. G. G. Danagulyan
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  2. V. A. Ostrovskii
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  3. V. K. Gharibyan
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Corresponding authors

Correspondence to G. G. Danagulyan or V. A. Ostrovskii.

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The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 11, pp. 1229–1233 https://doi.org/10.31857/S051474922211012X.

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Danagulyan, G.G., Ostrovskii, V.A. & Gharibyan, V.K. Regioselectivity of Alkylation of Azolo[1,5-a]pyrimidines. Russ J Org Chem 58, 1648–1651 (2022). https://doi.org/10.1134/S1070428022110136

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  • DOI: https://doi.org/10.1134/S1070428022110136

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