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Russian Journal of General Chemistry

, Volume 88, Issue 4, pp 836–838 | Cite as

Arylation of Pyridine with 9,10-Dioxoanthracenyl-1(2)-diazonium Hydrosulfates

  • M. V. Stasevych
  • V. I. Zvarych
  • V. V. Lunin
  • N. A. Kopak
  • V. P. Novikov
  • I. I. Chernobaev
  • M. V. Vovk
Letters to the Editor
  • 14 Downloads

Abstract

9,10-Dioxoanthracenyl-1(2)-diazonium hydrosulfates reacted with pyridine under both the modified Gomberg–Bachmann reaction conditions and in the presence of catalytic amounts of CuCl2 to form a mixture of isomeric 2-, 3-, and 4-pyridylanthraquinones, of which 2-pyridyl derivatives were isolated in an analytically pure form.

Keywords

9,10-dioxoanthracenyldiazonium salts pyridine arylation Gomberg–Bachmann reaction pyridylanthraquinones 

References

  1. 1.
    Hari, D.P., Scholl, P., and Konig, B., J. Am. Chem. Soc., 2012, vol. 134, p. 2958. doi 10.1021/ja212099rCrossRefGoogle Scholar
  2. 2.
    Singh, P.P., Aithagani, S.K., Yadav, M., Singh, V.P., and Vishmakarma, R.A., J. Org. Chem., 2013, vol. 78, p. 2639. doi 10.1021/jo302797rCrossRefGoogle Scholar
  3. 3.
    Hassan, J., Sevignon, M., Gozzi, C., Schulz, E., and Lemaire, M., Chem. Rev., 2002, vol. 102, p. 1359. doi 10.1021/cr000664rCrossRefGoogle Scholar
  4. 4.
    Sun, C.-L., Li, H., Yu, D.-G., Yu, M., Zhou, X., Lu, X., Huang, K., Zheng, S.-F., Li, B.-J., and Shi, Z.-J., Nat. Chem., 2010, vol. 2, p. 1044. doi 10.1038/nchem.862CrossRefGoogle Scholar
  5. 5.
    Galli, C., Chem. Rev., 1988, vol. 88, p. 765. doi 10.1021/cr00087a004CrossRefGoogle Scholar
  6. 6.
    Thiemann, T., Tanaka, Y., and Iniesta, J., Molecules, 2009, vol. 14, p. 1013. doi 10.3390/molecules14031013CrossRefGoogle Scholar
  7. 7.
    Akashi, H. and Oda, R., J. Chem. Soc. Japan, 1950, vol. 53, p. 202.Google Scholar
  8. 8.
    Obushak, N.D., Lesyuk, A.I., Ganushchak, N.I., Mel’nik, G.M., and Zavalii, P.Yu., Zh. Org. Khim., 1986, vol. 22, p. 2331.Google Scholar
  9. 9.
    Crisostomo, F.P., Martin, T., and Carrillo, R., Angew. Chem. Int. Ed., 2014, vol. 53, p. 2181. doi 10.1002/anie.201309761CrossRefGoogle Scholar
  10. 10.
    Perretti, M.D., Monzon, D.M., Crisostomo, F.P., Martin, V.S., and Carrillo, R., Chem. Commun., 2016, vol. 52, p. 9036. doi 10.1039/C5CC09911KCrossRefGoogle Scholar
  11. 11.
    Hata, D., Moriuchi, T., Hirao, T., and Amaya, T., Chem. Eur. J., 2017, vol. 23, p. 7703. doi 10.1002/chem.201700630CrossRefGoogle Scholar
  12. 12.
    Honraedt, A., Roux, M.-A., Le Grognec, E., Jacquemin, D., and Felpin, F.-X., Chem. Commun., 2014, vol. 50, p. 5236. doi 10.1039/c3cc45240aCrossRefGoogle Scholar
  13. 13.
    Klimenko, L.S., Mainagashev, I.Ya., and Fokin, E.P., Russ. Chem. Bull., 1992, vol. 41, p. 789. doi 10.1007/BF01150908CrossRefGoogle Scholar
  14. 14.
    Loskutov, V.A., Lukonina, S.M., Konstantinova, A.V., and Fokin, E.P., Zh. Org. Khim., 1981, vol. 17, p. 584.Google Scholar
  15. 15.
    Zvarych, V.I., Stasevych, M.V., Lunin, V.V., Vovk, M.V., and Novikov, V.P., Russ. J. Gen. Chem., 2016, vol. 86, p. 2699. doi 10.1134/S1070363216120227CrossRefGoogle Scholar
  16. 16.
    Gomberg, M. and Bachmann, W.E., J. Am. Chem. Soc., 1924, vol. 21, p. 3297. doi 10.1021/ja01675a026Google Scholar
  17. 17.
    Abramovitch, R.A. and Saha, J.G., Tetrahedron, 1965, vol. 21, p. 3297. doi 10.1016/S0040-4020(01)96951-0CrossRefGoogle Scholar
  18. 18.
    Chen, X., Zhou, L., Li, Y., Xie, T., and Zhou, S., J. Org. Chem., 2014, vol. 79, p. 230. doi 10.1021/j04024123CrossRefGoogle Scholar
  19. 19.
    Xi, L.-Y., Zhang, R.-Y., Liang, S., Chen, S.-Y., and Yu, X.-Q., Org. Lett., 2014, vol. 16, p. 5269. doi 10.1021/ol5023596CrossRefGoogle Scholar
  20. 20.
    Colombe, J.R., Bernhardt, S., Stathakis, C., Buchwald, S.L., and Knochel, P., Org. Lett., 2013, vol. 15, p. 5754. doi 10.1021/ol402798zCrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • M. V. Stasevych
    • 1
  • V. I. Zvarych
    • 1
  • V. V. Lunin
    • 1
  • N. A. Kopak
    • 1
  • V. P. Novikov
    • 1
  • I. I. Chernobaev
    • 2
  • M. V. Vovk
    • 2
  1. 1.Lviv Polytechnic National UniversityLvivUkraine
  2. 2.Institute of Organic Chemistry of the National Academy of Sciences of UkraineKievUkraine

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