Synthesis of 2-alkyl-1,2,4-triazolo[3,4-a]isoquinolin-2-ium bromides and hexafluorophosphates

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Abstract

Alkylation of 1,2,4-triazolo[3,4-a]isoquinolines with 1-bromoalkanes was carried out under microwave synthesis conditions; the resulting 2-alkyl-1,2,4-triazolo[3,4-a]isoquinolin-2-ium bromides were converted into hexafluorophosphates and characterized by high-resolution mass spectrometry, 1H, 13C NMR spectroscopy and X-ray diffraction analysis.

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About the authors

L. S. Ermakova

Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences

Email: glusha55@gmail.com
ORCID iD: 0009-0008-1397-6631
Russian Federation, 614068, Perm

N. O. Leont’ev

Perm State National Research University

Email: glusha55@gmail.com
ORCID iD: 0009-0000-9777-0658
Russian Federation, 614099, Perm

M. S. Denisov

Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences

Email: glusha55@gmail.com
ORCID iD: 0000-0002-8817-0543
Russian Federation, 614068, Perm

I. А. Borisova

Perm State National Research University

Email: glusha55@gmail.com
ORCID iD: 0000-0002-2261-8122
Russian Federation, 614099, Perm

М. V. Dmitriev

Perm State National Research University

Email: glusha55@gmail.com
ORCID iD: 0000-0002-0731-3400
Russian Federation, 614099, Perm

V. A. Glushkov

Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences; Perm State National Research University

Author for correspondence.
Email: glusha55@gmail.com
ORCID iD: 0000-0001-6493-7351
Russian Federation, 614068, Perm; 614099, Perm

References

  1. Pan Y., Tian R., Chen Y., Wang L., Qin H., Wang J. // Tetrahedron. 2023. Vol. 148. P. 133688. doi 10.1016/ j.tet.2023.133688
  2. Zhang W., Jiang R., Mu Y., Hong Y., Man Y., Yang Z., Tang D. // Tetrahedron Lett. 2023. Vol. 114. P. 154256. doi: 10.1016/j.tetlet.2022.154256
  3. Глушков В.А., Шкляев Ю.В., Майорова О.А., Постаногова Г.А., Фешина Е.В. // ХГС. 2000. Т. 36. С. 380; Glushkov V.A., Shklyaev Yu.V., Maiorova O.A., Postanogova G.A., Feshina E.V. // Chem. Heterocycl. Compd. 2000. Vol. 36. P. 319. doi: 10.1007/BF02256870
  4. Deady L.W., Devine S.M. // J. Heterocycl. Chem. 2004. Vol. 41. P. 549. doi: 10.1002/jhet.5570410411
  5. Chen Z., Chen S., Qui Z., Lin B., Yao Y., Weng Z. // J. Org. Chem. 2024. Vol. 89. P. 7163. doi 10/1021/acs.joc.4c00557
  6. Yount J., Morris M., Henson N., Zeller M., Byrd E.F.C., Piercey D.G. // Chem. Eur. J. 2024. Vol. 30. P. e202400661. doi: 10.1002/chem.202400661
  7. Badr S.M.I., Barwa R.M. // Bioorg. Med. Chem. 2011. Vol. 19. P. 4506. doi: 10.1016/j.bmc.2011.06.024
  8. Zhao P.-L., Duan A.-N., Zou M., Yang H.-K., You W.-W., Wu S.-G. // Bioorg. Med. Chem. Lett. 2012. Vol. 22. P. 4471. doi: 10.1016/j.bmcl.2012.03.023
  9. Yan X., Zhang C., Gao L.-X., Liu M.-M., Yang Y.-T., Yu L.-J., Zhou Y.-B., Milaneh S., Zhu Y.-L., Li J., Wang W.-L. // Eur. J. Med. Chem. 2024. Vol. 265. P. 116027. doi: 10.1016/j.ejmech.2023.116027
  10. Feitosa L.M., Franca R.R.F., Ferreira M. de L.G., Aguiar A.C.C., de Souza G.E., Maluf S.E.C., de Souza J.O., Zapata L., Duarte D., Morais I., Nogueira F., Nonato M.C., Pinheiro L.C.S., Guido R.V.C., Boechat N. // Eur. J. Med. Chem. 2024. Vol. 267. P. 116163. doi 10.1016/ j.ejmech.2024.116163; Ali I., Cha H.J., Lim B., Chae C.H., Youm J., Park W.J., Lee S.H., Kim J.H., Jeong D., Lim J.K., Hwang Y.-H., Roe J.-S., Woo J.-S., Lee K., Choi G. // Eur. J. Med. Chem. 2024. Vol. 265. 116052. doi 10.1016/ j.ejmech.2023.116052
  11. Ali I., Cha H.J., Lim B., Chae C.H., Youm J., Park W.J., Lee S.H., Kim J.H., Jeong D., Lim J.K., Hwang Y.-H., Roe J.-S., Woo J.-S., Lee K., Choi G. // Eur. J. Med. Chem. 2024. Vol. 265. 116052. doi 10.1016/ j.ejmech.2023.116052
  12. Носова Э.В., Копотилова А.Е., Иванькина М.А., Мошкина Т.Н., Копчук Д.С. // Изв. АН. Сер. хим. 2022. Т. 71. № 7. С. 1483; Nosova E.V., Kopotilova A.E., Ivan’kina M.A., Moshkina T.N., Kopchuk D.S. // Russ. Chem. Bull. 2022. Vol. 71. N 7. P. 1483. doi: 10.1007/s11172-022-3554-7
  13. Shtaitz Ya.K., Ladin E.D., Kopchuk D.S., Khalymbadzha I.A., Gaviko V.S., Zyryanov G.V., Antonenko D.V., Ostrovskii V.A., Rusinov V.L. // Russ. J. Gen. Chem. 2024. Vol. 94. P. 749. doi: 10.1134/S1070363224040029
  14. Русинов В.Л., Чарушин В.Н., Чупахин О.Н. // Изв. АН. Сер. хим. 2018. № 4. С. 573; Rusinov V.L., Charushin V.N., Chupakhin O.N. // Russ. Chem. Bull. 2018. Vol. 67. N 4. P. 573. doi: 10.1007/s11172-018-2113-8
  15. Машковский М.Д. Лекарственные средства. М.: Новая волна, 2019. С. 30, 83, 84.
  16. Ермакова Л.С., Грачева В.С., Майорова О.А., Дмитриев М.В., Белоглазова Ю.А., Глушков В.А. // Изв. АН. Сер. хим. 2024. Т. 73. С. 1072; Ermakova L.S., Gracheva V.S., Maiorova O.A., Dmitriev M.V., Beloglazova Yu.A., Glushkov V.A. // Russ. Chem. Bull. 2024. Vol. 73. P. 1072. doi: 10.1007/s11172-024-4222-x
  17. CrysAlisPro, Rigaku Oxford Diffraction, 2022. Version 1.171.42.74a.
  18. Sheldrick G.M. // Acta Crystallogr. (A). 2015. Vol. 71. P. 3. doi: 10.1107/S2053273314026370
  19. Sheldrick G.M. // Acta Crystallogr. (C). 2015. Vol 71. P. 3. doi: 10.1107/S2053229614024218
  20. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H.J. // Appl. Cryst. 2009. Vol 42. P. 339. doi: 10.1107/S0021889808042726

Supplementary files

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2. Scheme 1.

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3. Fig. 1. General view of the bromide molecule 2b according to X-ray diffraction data, represented by thermal ellipsoids of 30% probability.

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4. Fig. 2. General view of the bromide molecule 4a according to X-ray diffraction data, represented by thermal ellipsoids of 30% probability.

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