Russian Journal of Organic Chemistry

, Volume 55, Issue 1, pp 87–92 | Cite as

Trifluoroacetylation of N-Substituted 1H-1,2-Diazaphenalenes of the Naphthalene and Acenaphthene Series

  • N. I. OmelichkinEmail author
  • L. G. Minyaeva
  • M. S. Korobov
  • G. S. Borodkin
  • L. G. Kuz’mina
  • V. V. Mezheritskii


The acylation of N-substituted 3-methyl-1H-1,2-diazaphenalenes of the naphthalene and acenaphthene series with trifluoroacetic anhydride gave mono- and diacylated products. Despite the presence of a bulky substituent on the pyrrole type nitrogen atom, the trifluoroacetyl group entered the peri position with respect to that substituent. The product structure was confirmed by X-ray analysis.


1,2-diazaphenalenes electrophilic substitution trifluoroacetylation X-ray analysis 


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  1. 1.
    Elisevich, D.M., Okolelova, M.S. Kazakov, A.L., Drogovoz, S.M., and Luk’yanchikov, M.S., USSR Inventor’s Certificate no. 1394671, 1987.Google Scholar
  2. 2.
    Elisevich, D.M., Okolelova, M.S., Slyshkov, V.V., Kazakov, A.L., and Pokhil’ko, E.A., USSR Inventor’s Certificate no. 1487412.Google Scholar
  3. 3.
    Elisevich, D.M., Ivashev, M.N., Okolelova, M.S., and Lysenko, T.A., RU Patent no. 2049090, 1995.Google Scholar
  4. 4.
    Mezheritskii, V.V., Pikus, A.L., Spasov, A.A., Ostrovskii, O.V., Dudchenko, G.P., and Kosolapov, V.A., Pharm. Chem. J., 1998, vol. 32, no. 1, p. 13.CrossRefGoogle Scholar
  5. 5.
    Yarmoliuk, D.V., Arkhipov, V.V., Stambirskiy, M.V., Dmytriv, Yu.V., Shishkin, O.V., Tolmachev, A.A., and Mykhailiuk, P.K., Synthesis, 2014, vol. 46, p. 1254.CrossRefGoogle Scholar
  6. 6.
    Böhm, H-J., Banner, D., Bendeks, S., Kansy, M., Kuhn, B., Müller, K., Obst-Sander, U., and Stahl, M., ChemBioChem., 2004, vol. 5, p. 637.CrossRefGoogle Scholar
  7. 7.
    Elisevich, D.M., Mezheritskii, V.V., and Dorofeenko, G.N., Zh. Org. Khim., 1981, vol. 17, p. 1751.Google Scholar
  8. 8.
    Elisevich, D.M., Cand. Sci. (Chem.) Dissertation, Rostov-on-Don, 1982.Google Scholar
  9. 9.
    Yurchuk, G.G. and Pozharskii, A.F., Chem. Heterocycl. Compd., 1981, vol. 17, no. 8, p. 825.CrossRefGoogle Scholar
  10. 10.
    Pozharskii, A.F., Borovlev, I.V., and Kashparov, I.S., Chem. Heterocycl. Compd., 1975, vol. 11, no. 4, p. 480.CrossRefGoogle Scholar
  11. 11.
    Pozharskii, A.F. and Koroleva, V.N., Chem. Heterocycl. Compd., 1975, vol. 11, no. 4, p. 486.CrossRefGoogle Scholar
  12. 12.
    Omelichkin, N.I., Minyaeva, L.G., and Mezheritskii, V.V., Russ. J. Org. Chem., 2016, vol. 52, p. 562.CrossRefGoogle Scholar
  13. 13.
    Omelichkin, N.I., Kuz’mina, L.G., Minyaeva, L.G., and Mezheritskii, V.V., Russ. J. Org. Chem., 2017, vol. 53, p. 477.CrossRefGoogle Scholar
  14. 14.
    Mezheritskii, V.V., Minyaeva, L.G., Omelichkin, N.I., Borodkin, G.S., and Korobov, M.S., Russ. J. Org. Chem., 2015, vol. 51, p. 670.CrossRefGoogle Scholar
  15. 15.
    APEX2, SADABS and SAINT, Madison, Wiskonsin, USA: Bruker AXS.Google Scholar
  16. 16.
    Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, A.J.K., and Pushman, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • N. I. Omelichkin
    • 1
    Email author
  • L. G. Minyaeva
    • 1
  • M. S. Korobov
    • 1
  • G. S. Borodkin
    • 1
  • L. G. Kuz’mina
    • 2
  • V. V. Mezheritskii
    • 1
  1. 1.Research Institute of Physical and Organic ChemistrySouthern Federal UniversityRostov-on-DonRussia
  2. 2.Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussia

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