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Synthesis of 3-tert-Butyl-4-hydroxy-1,4-dihydropyrazolo[5,1-c][1,2,4]triazines

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Abstract

Two new approaches have been proposed for the synthesis of 4-hydroxy-1,4-dihydropyrazolo[5,1-c]-[1,2,4]triazines via (1) borohydride reduction of 1-R-4-oxo-1,4-dihydro derivatives and (2) Vilsmeier formylation of 3-tert-butyl-8-methylpyrazolo[5,1-c][1,2,4]triazine. 3-tert-Butylpyrazolo[5,1-c][1,2,4]triazin-1(5)-ium cation has been generated for the first time by treatment of 7-amino-1-benzyl-3-tert-butyl-4-hydroxy-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carbonitrile with trifluoroacetic acid in CDCl3. The hydrolysis of 4-alkoxy-1,4-dihydropyrazolo[5,1-c][1,2,4]triazines was monitored by 1H and 13C NMR spectroscopy. The structure of the synthesized compounds was confirmed by spectral and X-ray diffraction data.

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REFERENCES

  1. Bodzioch, A., Pomikło, D., Celeda, M., Pietrzak, A., and Kaszynski, P., J. Org. Chem., 2019, vol. 84, p. 6377. https://doi.org/10.1021/acs.joc.9b00716

    Article  CAS  PubMed  Google Scholar 

  2. Obijalska, E. and Kowalski, M.K., Chem. Heterocycl. Compd., 2017, vol. 53, p. 846. https://doi.org/10.1007/s10593-017-2134-5

    Article  CAS  Google Scholar 

  3. Mirallai, S.I., Koutentis, P.A., and Aldabbagh, F., Molecules, 2019, vol. 24, article no. 282. https://doi.org/10.3390/molecules24020282

    Article  Google Scholar 

  4. Ott, G.R. and Favor, D.A., Bioorg. Med. Chem. Lett., 2017, vol. 27, p. 4238. https://doi.org/10.1016/j.bmcl.2017.07.073

    Article  CAS  PubMed  Google Scholar 

  5. Song, Y., Zhan, P., Zhang, Q., and Liu, X., Curr. Pharm. Des., 2013, vol. 19, p. 1528. https://doi.org/10.2174/1381612811319080020

    Article  CAS  PubMed  Google Scholar 

  6. Piercey, D.G., Chavez, D.E., Scott, B.L., Imler, G.H., and Parrish, D.A., Angew. Chem., Int. Ed., 2016, vol. 55, p. 15315. https://doi.org/10.1002/anie.201608723

    Article  CAS  Google Scholar 

  7. Su, C., Yan, Y., Guo, X., Luo, J., Liu, C., Zhang, Z., Xiang, W.-S., and Huang, S.-X., Org. Biomol. Chem., 2019, vol. 17, p. 477. https://doi.org/10.1039/C8OB02847H

    Article  CAS  PubMed  Google Scholar 

  8. Rusinov, V.L., Charushin, V.N., and Chupakhin, O.N., Russ. Chem. Bull., Int. Ed., 2018, vol. 67, p. 573. https://doi.org/10.1007/s11172-018-2113-8

    Article  CAS  Google Scholar 

  9. Hamama, W.S., El–Bana, G.G., Mostafa, M.El–H., and Zoorob, H.H.,J. Heterocycl. Chem., 2019, vol. 56, p. 239. https://doi.org/10.1002/jhet.3401

    Article  CAS  Google Scholar 

  10. Klug, C. and Sudowe, R., Sep. Sci. Technol., 2013, vol. 48, p. 2567. https://doi.org/10.1080/01496395.2013.805783

    Article  CAS  Google Scholar 

  11. Singh, B., Pandey, A., and Singh, S.K., Mol. Cryst. Liq. Cryst., 2010, vol. 517, p. 127. https://doi.org/10.1080/15421400903483957

    Article  CAS  Google Scholar 

  12. Kozhevnikov, V.N., Cowling, S.J., Karadakov, P.B., and Bruce, D.W.,J. Mater. Chem., 2008, vol. 18, p. 1703. https://doi.org/10.1039/B718432H

    Article  CAS  Google Scholar 

  13. Tang, Y., He, C., Imler, G.H., Parrish, D.A., and Shreeve, J.M.,Chem. Commun., 2018, vol. 54, p. 10566. https://doi.org/10.1039/C8CC05987J

    Article  CAS  Google Scholar 

  14. Wu, J.-T., Zhang, J.-G., Li, T., Li, Z.-M., and Zhang, T.-L.,RSC Adv., 2015, vol. 5, p. 28354. https://doi.org/10.1039/C5RA01124H

    Article  CAS  Google Scholar 

  15. Gorbunov, E.B., Ulomsky, E.N., Voinkov, E.K., Drokin, R.A., Lyapustin, D.N., Rusinov, G.L., Rusinov, V.L., Charushin, V.N., and Chupakhin, O.N., Synthesis, 2018, vol. 50, p. 4889. https://doi.org/10.1055/s-0037-1610244

    Article  CAS  Google Scholar 

  16. Dalinger, I.L., Vatsadze, I.A., Shkineva, T.K., Popova, G.P., Ugrak, B.I., and Shevelev, S.A., Russ. Chem. Bull., Int. Ed., 2010, vol. 59, p. 1631. https://doi.org/10.1007/s11172-010-0287-9

    Article  CAS  Google Scholar 

  17. Shchegol’kov, E.V., Ivanova, A.E., Burgart, Y.V., and Saloutin, V.I., J. Heterocycl. Chem., 2013, vol. 50, p. E80. https://doi.org/10.1002/jhet.1068

    Article  CAS  Google Scholar 

  18. Ivanov, S.M., Mironovich, L.M., Rodinovskaya, L.A., and Shestopalov, A.M., Russ. Chem. Bull., Int. Ed., 2018, vol. 67, p. 1487. https://doi.org/10.1007/s11172-018-2244-y

    Article  CAS  Google Scholar 

  19. Mironovich, L.M., Ivanov, S.M., and Daeva, E.D., Russ. J. Org. Chem., 2019, vol. 55, p. 958. https://doi.org/10.1134/S1070428019070066

    Article  CAS  Google Scholar 

  20. Ivanov, S.M., Lyssenko, K.A., Mironovich, L.M., and Shestopalov, A.M., Russ. Chem. Bull., Int. Ed., 2019, vol. 68, p. 1714. https://doi.org/10.1007/s11172-019-2615-z

    Article  CAS  Google Scholar 

  21. Ivanov, S.M., Mironovich, L.M., Kolotyrkina, N.G., and Shestopalov, A.M., Russ. Chem. Bull., Int. Ed., 2019, vol. 68, p. 614. https://doi.org/10.1007/s11172-019-2464-9

    Article  CAS  Google Scholar 

  22. Ivanov, S.M. and Shestopalov, A.M., J. Heterocycl. Chem., 2018, vol. 55, p. 1966. https://doi.org/10.1002/jhet.3236

    Article  CAS  Google Scholar 

  23. Ivanov, S.M., Dmitrienko, A.O., Medvedev, M.G., and Mironovich, L.M., J. Organomet. Chem., 2019, vol. 896, p. 168. https://doi.org/10.1016/j.jorganchem.2019.06.009

    Article  CAS  Google Scholar 

  24. Ivanov, S.M., Mironovich, L.M., Rodinovskaya, L.A., and Shestopalov, A.M., Tetrahedron Lett., 2017, vol. 58, p. 1851. https://doi.org/10.1016/j.tetlet.2017.03.083

    Article  CAS  Google Scholar 

  25. Ivanov, S.M., Dmitrenok, A.S., and Lyssenko, K.A., Tetrahedron Lett., 2019, vol. 60, article no. 151109. https://doi.org/10.1016/j.tetlet.2019.151109

    Article  Google Scholar 

  26. Ivanov, S.M. and Shestopalov, A.M., J. Heterocycl. Chem., 2018, vol. 55, p. 2427. https://doi.org/10.1002/jhet.3275

    Article  CAS  Google Scholar 

  27. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053273314026370

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Southwest State University, 305040, Kursk, Russia

    L. M. Mironovich

  2. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    S. M. Ivanov & N. G. Kolotyrkina

  3. Mendeleev University of Chemical Technology of Russia, 125047, Moscow, Russia

    S. M. Ivanov

Authors
  1. L. M. Mironovich
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  2. S. M. Ivanov
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  3. N. G. Kolotyrkina
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Correspondence to L. M. Mironovich.

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Mironovich, L.M., Ivanov, S.M. & Kolotyrkina, N.G. Synthesis of 3-tert-Butyl-4-hydroxy-1,4-dihydropyrazolo[5,1-c][1,2,4]triazines. Russ J Org Chem 56, 596–603 (2020). https://doi.org/10.1134/S1070428020040065

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