Non-Catalytic Synthesis of 5-(4-Cycloalkylamino)Phenyl(bi)pyridines

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

The possibility of non-catalytic ipso-substitution of the halogen atom in the para-position of the phenyl substituent in the C6 position of the 1,2,4-triazine ring by a cycloalkylamine group in the absence of a solvent was investigated. The possibility of transforming the obtained 1,2,4-triazines into the corresponding (bi)pyridines using the Bodger reaction with 2,5-norbornadiene under elevated pressure (using autoclave technology) was shown.

About the authors

S. E Vatolina

Ural Federal University

Yekaterinburg, Russia

A. P Krinochkin

Ural Federal University; Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Yekaterinburg, Russia; Yekaterinburg, Russia

T. A Tseytler

Ural Federal University; Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: t.a.tceytler@urfu.ru
Yekaterinburg, Russia

A. A Yurtaeva

Ural Federal University

Yekaterinburg, Russia

A. S Alekseeva

Ural Federal University

Yekaterinburg, Russia

A. S Markina

Ural Federal University

Yekaterinburg, Russia

V. S Gaviko

Ural Federal University; Institute of Physics of Metals, Ural Branch of the Russian Academy of Sciences

Yekaterinburg, Russia; Yekaterinburg, Russia

D. S Kopchuk

Ural Federal University; Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Yekaterinburg, Russia; Yekaterinburg, Russia

G. V Zyryanov

Ural Federal University; Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Yekaterinburg, Russia; Yekaterinburg, Russia

References

  1. Constable E.C., Housecroft C.E. Molecules. 2019, 24, art. 3951. https://doi.org/10.3390/molecules24213951
  2. Hancock R.D. Chem. Soc. Rev. 2013, 42, 1500–1524. https://doi.org/10.1039/C2CS35224A
  3. Зырянов Г.В., Липунова Г.Н., Носова Э.В., Тания О.С., Копчук Д.С. Пуш-пульные флуорофоры азинового ряда. В 2 частях. Ч. 1. Производные моноазинов и их аннелированные аналоги. Екатеринбург: Издательство АМБ, 2022. 240 с.
  4. Sharma A.N., Verma R. Chem. Biodiversity. 2023, 20, art. e202300764. https://doi.org/10.1002/cbdv.202300764
  5. Kozhevnikov V.N., Shabunina O.V., Kopchuk D.S., Ustinova M.M., König B., Kozhevnikov D.N. Tetrahedron. 2008, 64, 8963–8973. https://doi.org/10.1016/j.tet.2008.06.040
  6. Shabunina O.V., Kapustina D.Yu., Krinochkin A.P., Kim G.A., Kopchuk D.S., Zyryanov G.V., Fi L., Chupakhin O.N. Mendeleev Commun. 2017, 27, 602–604. https://doi.org/10.1016/j.mencom.2017.11.021
  7. Younes A.H., Zhang L., Clark R.J., Zhu L. J. Org. Chem. 2009, 74, 8761–8772. https://doi.org/10.1021/jo901889y
  8. Loren J.C., Siegel J.S. Angew. Chem., Int. Ed. 2001, 40, 754–757. https://doi.org/10.1002/1521-3773(20010216)40:4<754::AID-ANIE7540>3.0.CO;2-T
  9. Heravi M., Kheilkordi Z., Zadsirjan V., Heydari M., Malmir M. J. Organomet. Chem. 2018, 861, 17–104. https://doi.org/10.1016/j.jorganchem.2018.02.023
  10. Fallahpour R.-A. Synthesis. 2008, 1514–1516. https://doi.org/10.1055/s-2008-1072574
  11. Kohl T.M., Hornung C.H., Tsanaktsidis J. Molecules. 2015, 20, 17860. https://doi.org/10.3390/molecules201017860
  12. Desroy N., Denis A., Gerusz V., Oliveira C., Vongsouthi V., Moreau F., Escaich S. Пат. WO2010001220A1 (2010); C.A. 2010, 152, 144718.
  13. Zhang F.-G., Chen Z., Tang X., Ma J.-A. Chem. Rev. 2021, 121, 14555–14593. https://doi.org/10.1021/acs.chemrev.1c00611
  14. Штайц Я.К., Савчук М.И., Копчук Д.С., Тания О.С., Сантра С., Зырянов Г.В., Суворова А.И., Русинов В.Л., Чупахин О.Н. ЖОрХ. 2020, 56, 479–483.
  15. Shtaitz Ya.K., Savchuk M.I., Kopchuk D.S., Taniya O.S., Santra S., Zyryanov G.V., Suvorova A.I., Rusinov V.L., Chupakhin O.N. Russ. J. Org. Chem. 2020, 56, 548–551. https://doi.org/10.1134/S1070428020030306
  16. Kopchuk D.S., Krinochkin A.P., Starnovskaya E.S., Shtaitz Y.K., Khasanov A.F., Taniya O.S., Santra S., Zyryanov G.V., Majee A., Rusinov V.L., Chupakhin O.N. ChemistrySelect. 2018, 3, 4141–4146. https://doi.org/10.1002/slct.201800220
  17. Савчук М.И., Хасанов А.Ф., Копчук Д.С., Криночкин А.П., Никонов И.Л., Старновская Е.С., Штайц Я.К., Ковалев И.С., Зырянов Г.В., Чупахин О.Н. ХГС. 2019, 55, 554–559.
  18. Savchuk M.I., Khasanov A.F., Kopchuk D.S., Krinochkin A.P., Nikonov I.L., Starnovskaya E.S., Shtaitz Y.K., Kovalev I.S., Zyryanov G.V., Chupakhin O.N. Chem. Heterocycl. Compds. 2019, 55, 554–559. https://doi.org/10.1007/s10593-019-02495-5
  19. Шабунина О.В., Штайц Я.К., Копчук Д.С., Криночкин А.П., Сантра С., Зырянов Г.В., Ванг Ж., Русинов В.Л., Чупахин О.Н. ХГС. 2021, 57, 462–466.
  20. Shabunina O.V., Shtaitz Y.K., Kopchuk D.S., Krinochkin A.P., Santra S., Zyryanov G.V., Wang Zh., Rusinov V.L., Chupakhin O.N. Synthesis of novel 3-(pyridin-4-yl)-1,2,4-triazines, their analogs and study of the activity against vaccinia virus. Chem. Heterocycl. Compd. 2021, 57, 462–466. https://doi.org/10.1007/s10593-021-02924-4
  21. Kozhevnikov V.N., Kozhevnikov D.N., Shabunina O.V., Rusinov V.L., Chupakhin O.N. Tetrahedron Lett. 2005, 46, 1791–1793. https://doi.org/10.1016/j.tetlet.2005.01.135
  22. CrysAlisPro, version 1.171.39.38a, Data Collection, Reduction and Correction Program, Rigaku Oxford Diffraction, 2017.
  23. Sheldrick G.M. Acta Crystallogr. A. 2015, A71, 3–8. https://doi.org/10.1107/S2053273314026370
  24. Sheldrick G.M. Acta Crystallogr. С. 2015, C71, 3–8. https://doi.org/10.1107/S2053229614024218
  25. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H. J. Appl. Cryst. 2009, 42, 339–341. https://doi.org/10.1107/S0021889808042726

Supplementary files

Supplementary Files
Action
1. JATS XML

Copyright (c) 2025 Russian Academy of Sciences

Согласие на обработку персональных данных

 

Используя сайт https://journals.rcsi.science, я (далее – «Пользователь» или «Субъект персональных данных») даю согласие на обработку персональных данных на этом сайте (текст Согласия) и на обработку персональных данных с помощью сервиса «Яндекс.Метрика» (текст Согласия).