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

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Resumo

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.

Sobre autores

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

Bibliografia

  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

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