Reactions of 5-(1,2-dicarbadodecaboran-1-yl)-3-(2-pyridyl)1,2,4-triazines with dienophiles

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Abstract

The reactions of 5-(1,2-dicarbadodecaboran-1-yl)-3-(2-pyridyl)-1,2,4-triazines with various dienophiles (2,5-norbornadiene, 1-morpholinocyclopentene, 1,2-dehydrobenzene, and 2-amino-4-phenyloxazole) were studied. It was shown that the presence of a carborane fragment in the 1,2,4-triazine ring causes an atypical reaction with dienophiles without the formation of the expected aza -Diels-Alder reaction products except for the reaction with 2,5-norbornadiene. The reaction of 5-(1,2-dicarbadodecaboran-1-yl)-3-(2-pyridyl)-1,2,4triazines with 2-amino-4-phenyloxazole unexpectedly led to the formation of the corresponding 4,5-dihydro1,2,4-triazines. One of the previously described procedures for the direct introduction of a carborane residue into the C5 position of 1,2,4-triazines was optimized.

About the authors

M. I Valieva

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

A. Rammohan

Ural Federal University

E. S Starnovskaya

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

E. A Kudryashova

Ural Federal University

A. P Krinochkin

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

D. S Kopchuk

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

G. V Zyryanov

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

Email: gvzyryanov@gmail.com

O. N Chupakhin

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

References

  1. Chen Y., Du F., Tang L., Xu J., Zhao Y., Wu X., Li M., Shen J., Wen Q., Cho C.H., Xiao Z. // Molecular Therapy - Oncolytics. 2022. Vol. 24. P. 400. doi: 10.1016/j.omto.2022.01.005
  2. Dymova M.A., Taskaev S.Y., Richter V.A., Kuligina E.V. // Cancer Commun. 2020. Vol. 40. N 9. P. 406. doi: 10.1002/cac2.12089
  3. Smyshliaeva L.A., Varaksin M.V., Charushin V.N., Chupakhin O.N. // Synthesis. 2020. Vol. 52. N 3. P. 337. doi: 10.1055/s-0039-1690733
  4. Scholz M., Blobaum A.L., Marnett L.J., Hey-Hawkins E. // Bioorg. Med. Chem. 2012. Vol. 20. P. 4830. doi: 10.1016/j.bmc.2012.05.063
  5. Agarwal H.K., McElroy C.A., Sjuvarsson E., Eriksson S., Darby M.V., Tjarks W. // Eur. J. Med. Chem. 2013. Vol. 60. P. 456. doi: 10.1016/j.ejmech.2012.11.041
  6. da Silva A.F., Seixas R.S., Silva A.M., Coimbra J., Fernandes A. C., Santos J. P., Matos A., Rino J., Santos I., Marques F. // Org. Biomol. Chem. 2014. Vol. 12. P. 5201. doi: 10.1039/C4OB00644E
  7. Ковалев И.С., Копчук Д.С., Зырянов Г.В., Русинов В.Л., Чупахин О.Н., Чарушин В.Н. // Усп. хим. 2015. Т. 84. Вып. 12. С. 1191
  8. Kovalev I.S., Kopchuk D.S, Zyryanov G.V, Rusinov V.L, Chupakhin O.N, Charushin V.N. // Russ. Chem. Rev. 2015. Vol. 84. N 12. P. 1191. doi: 10.1070/RCR4462
  9. Galliamova L.A., Varaksin M.V., Chupakhin O.N., Slepukhin P.A., Charushin V.N. // Organometallics. 2015. Vol. 34. N 21. P. 5285. doi: 10.1021/acs.organomet.5b00736.
  10. Чупахин О.Н., Прохоров А.М., Кожевников Д.Н., Русинов В.Л., Глухов И.А., Старикова З.А., Ольшевская В.А., Калинин В.Н., Антипин М.Ю. // Изв. АН. Сер. хим. 2004. № 6. С. 1175
  11. Chupakhin O.N., Prokhorov A.M., Kozhevnikov D.N., Rusinov V.L., Glukhov I.A., Starikova Z.A., Ol'shevskaya V.A., Kalinin V.N., Antipin M.Yu. // Russ. Chem. Bull. 2004. Vol. 53. N 6. P. 1223. doi: 10.1023/B:RUCB.0000042277.99035.a8
  12. Prokhorov A.M., Kozhevnikov D.N., Rusinov V.L., Chupakhin O.N., Glukhov I.V., Antipin M.Yu., Kazheva O.N., Chekhlov A.N., Dyachenko O.A. // Organometallics. 2006. Vol. 25. N 12. P. 2972. doi: 10.1021/om051058v
  13. Prokhorov A.M., Hofbeck T., Czerwieniec R., Suleymanova A.F., Kozhevnikov D.N., Yersin H. // J. Am. Chem. Soc. 2014. Vol. 136 N 27. P. 9637. doi: 10.1021/ja503220w
  14. Varaksin M.V., Smyshliaeva L.A., Rusinov V.L., Makeev O.G., Melekhin V.V., Baldanshirieva A.D., Gubina O.G., Charushin V.N., Chupakhin O.N. // Tetrahedron. 2021. Vol. 102. P. 132525. doi: 10.1016/j.tet.2021.132525
  15. Прохоров А.М., Кожевников Д.Н. // ХГС. 2012. Т. 48. № 8. С. 1237
  16. Prokhorov A.M., Kozhevnikov D.N. // Chem. Heterocycl. Compd. 2012. Vol. 48. N 8. P. 1153. doi: 10.1007/s10593-012-1117-9
  17. Foster R.A.A., Willis M.C. // Chem. Soc. Rev. 2013. Vol. 42. P. 63. doi: 10.1039/C2CS35316D
  18. Kopchuk D.S., Nikonov I.L., Khasanov A.F., Giri K., Santra S., Kovalev I.S., Nosova E.V., Gundala S., Venkatapuram P., Zyryanov G.V., Majee A., Chupakhin O.N. // Org. Biomol. Chem. 2018. Vol. 16. P. 5119. doi: 10.1039/C8OB00847G
  19. Kopchuk D.S., Chepchugov N.V., Khasanov A.F., Kovalev I.S., Santra S., Nosova E.V., Zyryanov G.V., Majee A., Rusinov V.L., Chupakhin O.N. // Tetrahedron Lett. 2016. Vol. 57. N 34. P. 3862. doi: 10.1016/j.tetlet.2016.07.052
  20. Kozhevnikov V.N., Shabunina O.V., Kopchuk D.S., Ustinova M.M., König B., Kozhevnikov D.N. // Tetrahedron. 2008. Vol. 64. P. 8963. doi: 10.1016/j.tet.2008.06.040
  21. Kopchuk D.S., Krinochkin A.P., Kozhevnikov D.N., Slepukhin P.A. // Polyhedron. 2016. Vol. 118. P. 30. doi: 10.1016/j.poly.2016.07.025
  22. Kozhevnikov V.N., Kozhevnikov D.N., Nikitina T.V., Rusinov V.L., Chupakhin O.N., Zabel M., König B. // J. Org. Chem. 2003. Vol. 68. N 7. P. 2882. doi: 10.1021/jo0267955
  23. Kopchuk D.S., Khasanov A.F., Kovalev I.S., Zyryanov G.V., Rusinov V.L., Chupakhin O.N. // Mendeleev Commun. 2013. Vol. 23. N 4. P. 209. doi: 10.1016/j.mencom.2013.07.010
  24. Chepchugov N.V., Kopchuk D.S., Kovalev I.S., Zyryanov G.V., Rusinov V.L., Chupakhin O.N. // Mendeleev Commun. 2016. Vol. 26. N 3. P. 220. doi: 10.1016/j.mencom.2016.04.014
  25. Sainz Y.F., Raw S.A., Taylor R.J.K. // J. Org. Chem. 2005. Vol. 70. N 24. P. 10086. doi: 10.1021/jo051830
  26. Krinochkin A.P., Reddy G.M., Kopchuk D.S., Slepukhin P.A., Shtaitz Y.K., Khalymbadzha I.A., Kovalev I.S., Kim G.A., Ganebnykh I.N., Zyryanov G.V., Chupakhin O.N., Charushin V.N. // Mendeleev Commun. 2021. Vol. 31. P. 542. doi: 10.1016/j.mencom.2021.07.035
  27. Кондратьева Г.Я., Айтжaнова M.А., Богданов B.C., Сташина Г.А., Седишев И.П. // ХГС. 2000. Т. 36. № 8. С. 1128
  28. Kondrat'eva G.Ya., Aitzhanova M.A., Bogdanov V.S., Stashina G.A., Sedishev I.P. // Chem. Heterocycl. Compd. 2000. Vol. 36. N 8. P. 989. doi: 10.1007/BF02256987
  29. Kozhevnikov V.N., Kozhevnikov D.N., Shabunina O.V., Rusinov V.L., Chupakhin O.N. // Tetrahedron Lett. 2005. Vol. 46. P. 1791. doi: 10.1016/j.tetlet.2005.01.135
  30. Turner W.W., Arnold L.D., Maag H., Zlotnick A. Pat. WO 20150138895A1 (2015).

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