- PII
- 10.31857/S0044460X2303006X-1
- DOI
- 10.31857/S0044460X2303006X
- Publication type
- Article
- Status
- Published
- Authors
- Volume/ Edition
- Volume 93 / Issue number 3
- Pages
- 379-384
- 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.
- Keywords
- 5-(1,2-дикарбадодекаборан-1-ил)-3-(2-пиридил)-1,2,4-триазины реакция аза-Дильса-Альдера диенофилы реакции без использования растворителей восстановление нуклеофильное замещение водорода
- Date of publication
- 17.09.2025
- Year of publication
- 2025
- Number of purchasers
- 0
- Views
- 13
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. doi10.1055/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).
