Direct cross-dehydrogenative С–N-coupling of phenanthridine with 1H-benzotriazole

Мұқаба

Дәйексөз келтіру

Толық мәтін

Аннотация

An approach was developed for the direct C( sp 2)-H-functionalization of phenanthridine with a 1 H -benzotriazole residue, carried out in the presence of Selectfluor® reagent and leading to the formation of a C( sp 2)-N bond. The procedure described in this communication makes it possible to obtain α-(1 H -benzotriazol-1-yl)phenanthridine, which is a valuable synthon for further chemical transformations, in one step and using commercially available substrates and reagents.

Авторлар туралы

A. Akulov

Ural Federal University named after the first President of Russia B.N. Yeltsin

A. Pershin

Ural Federal University named after the first President of Russia B.N. Yeltsin

D. Kopchuk

Ural Federal University named after the first President of Russia B.N. Yeltsin;I.Ya. Postovsky Institute of Organic Synthesis, Russian Academy of Sciences, Ural Branch of the Russian Academy of Sciences

M. Varaksin

Ural Federal University named after the first President of Russia B.N. Yeltsin;I.Ya. Postovsky Institute of Organic Synthesis, Russian Academy of Sciences, Ural Branch of the Russian Academy of Sciences

G. Zyryanov

Ural Federal University named after the first President of Russia B.N. Yeltsin;I.Ya. Postovsky Institute of Organic Synthesis, Russian Academy of Sciences, Ural Branch of the Russian Academy of Sciences

Email: gvzyryanov@gmail.com

O. Chupakhin

Ural Federal University named after the first President of Russia B.N. Yeltsin;I.Ya. Postovsky Institute of Organic Synthesis, Russian Academy of Sciences, Ural Branch of the Russian Academy of Sciences

Әдебиет тізімі

  1. Taniya O.S., Kopchuk D.S., Khasanov A.F., Kovalev S.I., Santra S., Zyryanov G.V., Majee A., Charushin V.N., Chupakhin O.N. Coord. Chem. Rev. 2021, 442, 213980. doi: 10.1016/j.ccr.2021.213980
  2. Tumir L.M., Radić Stojković M., Piantanida I. Beilstein J. Org. Chem. 2014, 10, 2930-2954. doi: 10.3762/bjoc.10.312
  3. Pipe D.F., Rees C.W. J. Chem. Soc., Chem. Commun. 1982, 9, 520-521. doi: 10.1039/C39820000520
  4. Houghton P.G., Pipe D.F., Rees C.W., J. Chem. Soc., Perkin Trans. 1. 1985, 1471-1479. doi: 10.1039/P19850001471
  5. Murakami K., Yamada S., Kaneda T., Itami K., Chem. Rev. 2017, 117, 9302-9332. doi: 10.1021/acs.chemrev.7b00021
  6. Mukherjee A., Akulov A.A., Santra S., Varaksin M.V., Kim G.A., Kopchuk D.S., Taniya O.S., Zyryanov G.V., Chupakhin O.N. RSC Adv. 2022, 12, 9323-9341. doi: 10.1039/d2ra00260d
  7. Taniya O.S., Khasanov A.F., Varaksin M.V., Starnovskaya E.S., Krinochkin A.P., Savchuk M.I., Kopchuk D.S., Kovalev I.S., Kim G.A., Nosova E.V., Zyryanov G.V., Chupakhin O.N. New J. Chem. 2021, 45, 20955-20971. doi: 10.1039/d1nj03531b
  8. Santra S., Khasanov A.F., Mukherjee A., Rahman M., Kovalev I.S., Kopchuk D.S., Zyryanov G.V., Majee A., Chupakhin O.N., Charushin V.N. Eur. J. Org. Chem. 2018, 2018, 4351-4375. doi: 10.1002/ejoc.201800635
  9. Taniya O.S., Kopchuk D.S., Khasanov A.F., Kovalev I.S., Santra S., Rahman M., Zyryanov G.V., Majee A., Charushin V.N., Chupakhin O.N. New J. Chem. 2019, 43, 11382-11390. doi: 10.1039/c9nj01813a
  10. Akulov A.A., Varaksin M.V., Tsmokalyuk A.N., Charushin V.N., Chupakhin O.N. Green Chem. 2021, 23, 2049-2057. doi: 10.1039/D1GC00175B
  11. Акулов А.А., Вараксин М.В., Чарушин В.Н., Чупахин О.Н. ХГС. 2019, 55, 783-787.
  12. Akulov A.A., Varaksin M.V., Charushin V.N., Chupakhin O.N. Chem. Heterocycl. Compd. 2019, 55, 783-787. doi: 10.1039/D1GC00175B
  13. Xie L.Y., Qu J., Peng S., Liu K.J., Wang Z., Ding M.H., Wang Y., Cao Z., He W.M. Green Chem. 2018, 20, 760-764. doi: 10.1039/c7gc03106h
  14. Morgan G.T., Walls L.P. J. Chem. Soc. 1932, 2225-2231. doi: 10.1039/JR9320002225
  15. Parenty A.D.C., Smith L.V., Pickering A.L., Long D.-L., Cronin L. J. Org. Chem. 2004, 69, 5934-5946. doi: 10.1021/jo0495440
  16. Couturier M., Caron L., Tumidajski S., Jones K., White T.D. Org. Lett. 2006, 8, 1929-1932. doi: 10.1021/ol060473w
  17. Kim D., Ghosh P., Kwon N.Y., Han S.H., Han S., Mishra N.K., Kim S., Kim I.S. J. Org. Chem. 2020, 85, 2476-2485. doi: 10.1021/acs.joc.9b03173
  18. Yan L., Zhao D., Lan J., Cheng Y., Guo Q., Li X., Wu N., You J. Org. Biomol. Chem. 2013, 11, 7966-7977. doi: 10.1039/C3OB41760C

Қосымша файлдар

Қосымша файлдар
Әрекет
1. JATS XML
Жүктеу

© Russian Academy of Sciences, 2023

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).