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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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