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Synthesis of Polysubstituted Pyridopyrimidines, Pyrimidines, and Pyrazoles Based on 1,1-Bis(1H-benzotriazol-1-yl)-and 1,1-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-3,4,4-trichloro-2-nitrobuta-1,3-dienes

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Abstract

The reaction of 3,4,4-trichloro-1,1-bis(3,5-dimethyl-1H-pyrazol-1-yl)-2-nitrobuta-1,3-diene with 2-aminopyridine gave a polysubstituted pyrido[1,2-a]pyrimidine derivative with an aminopyridine residue in the 2-position, whereas heterocyclization of 3,4,4-trichloro-1,1-bis(1H-benzotriazol-1-yl)-2-nitrobuta-1,3-diene with substituted 2-aminopyridines afforded 2-(1H-berrzotriazol-1-yl)pyrido[1,2-a]pyrimidines. 2-(Morpholin-4-yl), 2-amino, and 2-(2-hydroxyethylamino) derivatives of polysubstituted pyrido[1,2-a]pyrimidines were synthesized, and those containing a 2-hydroxyethylamino group were converted to the corresponding 4,5-dichloro-1,2-thiazole-1-carboxylates. Specific features of heterocyclizations of benzotriazolyl and dimethylpyrazolyl derivatives of trichloronitro-1,3-butadiene to pyrimidine and pyrazole systems were revealed.

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Acknowledgments

The authors thank Dr. A.P. Tyurin (Gauze Research Institute of New Antibiotics, Russian Academy of Sciences, Moscow, Russia) for biological testing of some of the synthesized compounds.

Funding

This study was performed under financial support by the Belarusian Republican Foundation for Basic Research (project no. X18M-023).

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk, 220072, Belarus

    I. A. Kolesnyk, S. K. Petkevich, A. D. Tsaryk & V. I. Potkin

  2. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Minsk, 220141, Belarus

    P. V. Kurman

Authors
  1. I. A. Kolesnyk
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  2. S. K. Petkevich
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  3. A. D. Tsaryk
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  5. V. I. Potkin
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Corresponding author

Correspondence to I. A. Kolesnyk.

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The authors declare the absence of conflict of interest.

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Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 1, pp. 31–40.

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Kolesnyk, I.A., Petkevich, S.K., Tsaryk, A.D. et al. Synthesis of Polysubstituted Pyridopyrimidines, Pyrimidines, and Pyrazoles Based on 1,1-Bis(1H-benzotriazol-1-yl)-and 1,1-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-3,4,4-trichloro-2-nitrobuta-1,3-dienes. Russ J Org Chem 56, 20–28 (2020). https://doi.org/10.1134/S1070428020010042

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  • DOI: https://doi.org/10.1134/S1070428020010042

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