INTERACTION OF 2-AMINO-(4-ARYL)-SUBSTITUTED THIA- AND OXAZOLES WITH 5-CYANO-1,2,4-TRIAZINES

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

An interaction of 6-aryl-1,2,4-triazine-5-carbonitriles with 2‑amino-substituted thiazoles and oxazoles has been studied. The difference in the reactivity of these aminoheterocycles depending on the presence of an oxygen or sulfur atom in their composition has been demonstrated. Previously, the 4-aryl-3-hydroxy-2,2'-bipyridines were obtained as products of aza-Diels–Alder reaction between 6-aryl-3-(2-pyridyl)-1,2,4-triazine-5-carbonitriles and 2-amino-4-aryloxazoles. In the present work we have shown that the reaction of 6-aryl-1,2,4-triazine-5-carbonitriles with 2-aminothiazoles led to the products of ipso-substitution of cyano-group. The aza-Diels–Alder reaction of these compounds with 2,5-norbornadiene allowed to obtain (2,2'-bi)pyridines with the thiazol-2-amine moiety at alpha-position.

作者简介

A. Krinochkin

Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620219, Yekaterinburg

A. Matern

Ural Federal University

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg

G. Zyryanov

Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620219, Yekaterinburg

O. Taniya

Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620219, Yekaterinburg

E. Sharafieva

Ural Federal University; Ural State Medical University, Ministry of Healthcare of the Russian Federation

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620028, Yekaterinburg

E. Ladin

Ural Federal University

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg

D. Kopchuk

Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620219, Yekaterinburg

Ya. Shtaitz

Ural Federal University

编辑信件的主要联系方式.
Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg

A. Rammohan

Ural Federal University

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg

O. Chupakhin

Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Email: iaroslav.shtaits@urfu.ru
Russian, 620002, Yekaterinburg; Russian, 620219, Yekaterinburg

参考

  1. Atwood J.L., Davies J.E.D., MacNicol D.D., Vögtle F., Lehn J.-M. Comprehensive Supramolecular Chemistry. Oxford: Pergamon, 1996.
  2. Kaes C., Katz A., Hosseini M.W. // Chem. Rev. 2000. V. 100. P. 3553–3590. https://doi.org/10.1021/cr990376z
  3. Hancock R.D. // Chem. Soc. Rev. 2013. V. 42. P. 1500–1524. https://doi.org/10.1039/C2CS35224A
  4. Constable E.C., Housecroft C.E. // Molecules. 2019. V. 24. P. 3951. https://doi.org/10.3390/molecules24213951
  5. Prokhorov A.M., Kozhevnikov D.N. // Chem. Heterocycl. Compd. 2012. V. 48. P. 1153–1176. https://doi.org/10.1007/s10593-012-1117-9
  6. Anderson E.D., Boger D.L. // J. Am. Chem. Soc. 2011. V. 133. P. 12285–12292. https://doi.org/10.1021/ja204856a
  7. Charushin V.N., Chupakhin O.N. Metal Free C–H Functionalization of Aromatics, Nucleophilic Displacement of Hydrogen, in Topics in Heterocyclic Chemistry. Maes B.U.W., Cossy J., Polanc S. (Eds.). Springer, 2014. V. 37. P. 1–50.
  8. Kozhevnikov D.N., Rusinov V.L., Chupakhin O.N. // Adv. Heterocycl. Chem. 2002. V. 82. P. 261–305. https://doi.org/10.1016/S0065-2725(02)82029-3
  9. Huang J.J. // J. Org. Chem. 1985. V. 50. P. 2293–2298. https://doi.org/10.1021/jo00213a019
  10. Kozhevnikov D.N., Kozhevnikov V.N., Kovalev I.S., Rusinov V.L., Chupakhin O.N., Aleksandrov G.G. // Russ. J. Org. Chem. 2002. V. 38. P. 744–750. https://doi.org/10.1023/A:1019631610505
  11. Rykowski A., Branowska D., Makosza M., Van Ly P. // J. Heterocycl. Chem. 1996. V. 33. P. 1567–1571. https://doi.org/10.1002/jhet.5570330603
  12. Savchuk M.I., Starnovskaya E.S., Shtaitz Y.K., Kop-chuk D.S., Nosova E.V., Zyryanov G.V., Rusinov V.L., Chupakhin O.N. // Russ. J. Gen. Chem. 2018. V. 88. P. 2213–2215. https://doi.org/10.1134/S1070363218100316
  13. Ohba S., Konno S., Yamanaka H. // Chem. Pharm. Bull. 1991. V. 39. P. 486–488. https://doi.org/10.1248/cpb.39.486
  14. Kopchuk D.S., Chepchugov N.V., Kovalev I.S., Santra S., Rahman M., Giri K., Zyryanov G.V., Majee A., Charu-shin V.N., Chupakhin O.N. // RSC Adv. 2017. V. 7. P. 9610–9619. https://doi.org/10.1039/c6ra26305d
  15. 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. V. 3. P. 4141–4146. https://doi.org/10.1002/slct.201800220
  16. Krinochkin A.P., Guda M.R., Kopchuk D.S., Sloves-nova N.V., Kovalev I.S., Savchuk M.I., Shtaitz Ya.K., Starnovskaya E.S., Zyryanov G.V., Chupakhin O.N. // Russ. J. Org. Chem. 2021. V. 57. P. 1753–1756. https://doi.org/10.1134/S1070428021100262
  17. Krinochkin A.P., Guda M.R., Kopchuk D.S., Shtaitz Ya.K., Savateev K.V., Ulomsky E.N., Zyryanov G.V., Rusinov V.L., Chupakhin O.N. // Russ. J. Org. Chem. 2022. V. 58. P. 188–191. https://doi.org/10.1134/S1070428022020051
  18. Krinochkin A.P., Reddy G.M., Kopchuk D.S., Slepu-khin P.A., Shtaitz Ya.K., Khalymbadzha I.A., Kovalev I.S., Kim G.A., Ganebnykh I.N., Zyryanov G.V., Chupa-khin O.N., Charushin V.N. // Mendeleev Commun. 2021. V. 31. P. 542–544. https://doi.org/10.1016/j.mencom.2021.07.035
  19. Rammohan A., Krinochkin A.P., Kopchuk D.S., Shtaitz Ya.K., Savchuk M.I., Starnovskaya E.S., Zyrya-nov G.V., Rusinov V.L., Chupakhin O.N. // Russ. J. Org. Chem. 2022. V. 58. P. 180–183. https://doi.org/10.1134/S1070428022020038
  20. Kozhevnikov V.N., Kozhevnikov D.N., Nikitina T.V., Rusinov V.L., Chupakhin O.N., Zabel M., König B. // J. Org. Chem. 2003. V. 68. P. 2882–2888. https://doi.org/10.1021/jo0267955
  21. Krayushkin M.M., Sedishev I.P., Yarovenko V.N., Zavarzin I.V., Kotovskaya S.K., Kozhevnikov D.N., Charu-shin V.N. // Russ. J. Org. Chem. 2008. V. 44. P. 407–411. https://doi.org/10.1134/S1070428008030160
  22. Shafikov M.Z., Kozhevnikov D.N., Bodensteiner M., Brandl F., Czerwieniec R. // Inorg. Chem. 2016. V. 55. P. 7457–7466. https://doi.org/10.1021/acs.inorgchem.6b00704
  23. Krinochkin A.P., Shtaitz Y.K., Rammohan A., Butorin I.I., Savchuk M.I., Khalymbadzha I.A., Kopchuk D.S., Slepukhin P.A., Melekhin V.V., Shcheglova A.V., Zyrya-nov G.V., Chupakhin O.N. // Eur. J. Org. Chem. 2022. e202200227. https://doi.org/10.1002/ejoc.202200227
  24. Kozhevnikov D.N., Kozhevnikov V.N., Prokhorov A.M., Ustinova M.M., Rusinov V.L., Chupakhin O.N., Aleksandrov G.G., König B. // Tetrahedron Lett. 2006. V. 47. P. 869–872. https://doi.org/10.1016/j.tetlet.2005.12.006
  25. Krinochkin A.P., Kopchuk D.S., Kozhevnikov D.N. // Polyhedron. 2015. V. 102. P. 556–561. https://doi.org/10.1016/j.poly.2015.09.055
  26. Kopchuk D.S., Krinochkin A.P., Khasanov A.F., Kova-lev I.S., Slepukhin P.A., Starnovskaya E.S., Mukherjee A., Rahman M., Zyryanov G.V., Majee A., Rusinov V.L., Chupakhin O.N., Santra S. // Synlett. 2018. V. 29. P. 483–488. https://doi.org/10.1055/s-0036-1590961

补充文件

附件文件
动作
1. JATS XML
下载
2.

下载 (91KB)
索引源数据

版权所有 © А.П. Криночкин, А. Раммохан, Я.К. Штайц, Д.С. Копчук, Е.Д. Ладин, Э.Р. Шарафиева, О.С. Тания, Г.В. Зырянов, А.И. Матерн, О.Н. Чупахин, 2023