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Synthesis of N-Arylquinone Diimine Derivatives of 2H-Benzimidazo[2,1-e]acridine and Their Reactions with Aromatic Amines

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Abstract

Oxidative coupling of 6,7,8,9,9a,10,11,12,13,14-decahydro-5H-benzimidazo[2,1-e]acridine with reagents containing a primary aromatic amino group forms p-quinone diimines of the 2H-benzimidazo[2,1-e]-acridine series. The subsequent acid-activated 1,4-nucleophilic addition reaction of the products with the same reagents followed by autooxidation gives rise to 3-arylamino-substituted quinone diimines of the specified series.

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References

  1. Vorozhtsov, N.N., Osnovy sinteza promezhutochnykh produktov i krasitelei (Basics of Synthesis of Intermediate Products and Dyes), Moscow: Goskhimizdat, 1955.

    Google Scholar 

  2. Clapp, R.C., Clark, J.H., English, J.P., Fellows, C.E., Grotz, R.E., and Shepherd, R.G., J. Am. Chem. Soc., 1952, vol.74, p.1989.

    Article  CAS  Google Scholar 

  3. Palling, D.J., Broun, K.C., and Corbett, J.F., J. Chem. Soc., Perkin Trans. 2, 1986, p.65.

    Google Scholar 

  4. Kubo, Y., Kuwana, M., Okamoto, K., and Yoshida, K., J. Chem. Soc., Perkin Trans. 1, 1990, p.1975.

    Google Scholar 

  5. Wei, Y., Yang, C., and Ding, T., Tetrahedron Lett., 1996, vol.37, p.731.

    Article  CAS  Google Scholar 

  6. Tawa, R. and Hirose, Sh., Chem. Pharm. Bull., 1980, vol.28, p.2136.

    Article  CAS  Google Scholar 

  7. Allan, L.T. and Swan, G.A., J. Chem. Soc., 1965, vol.III, p.3892.

    Google Scholar 

  8. Eremenko, I.L., Nefedov, S.E., Sidorov, A.A., Ponina, M.O., Danilov, P.V., Stromnova, T.A., Stolarov, I.P., Katser, S.B., Orlova, S.T., Vargaftik, M.N., Moiseev, I.I., and Ustynyuk, Yu.A., J. Organomet. Chem., 1998, vol.551, p.171.

    Article  CAS  Google Scholar 

  9. Kehrmann, F., Lieb. Ann., 1902, vol.322, p.1.

    Article  CAS  Google Scholar 

  10. Andreani, F., Bizzarri, P.C., Casa, C.D., Florini, M., and Salatelli, E., J. Heterocycl. Chem., 1991, vol.28, p.295.

    Article  CAS  Google Scholar 

  11. Slabko, O.Yu., Kaminskii, V.A., and Tilichenko, M.N., Chem. Heterocycl. Compd., 1989, vol.25, p.1254. doi https://doi.org/10.1007/BF00481519

    Article  Google Scholar 

  12. Slabko, O.Yu., Ageenko, N.V., and Kaminskii, V.A., Russ. J. Org. Chem., 2009, vol.45, p.266. doi https://doi.org/10.1134/S1070428009020195

    Article  CAS  Google Scholar 

  13. Babaev, E.V. and Tikhomirov, G.A., Chem. Heterocycl. Compd., 2005, vol.41, p.119. doi https://doi.org/10.1007/s10593-005-0117-4

    Article  CAS  Google Scholar 

  14. Kotovskaya, S.K., Baskakova, Z.M., Charushin, V.N., Chupakhin, O.N., Belanov, E.F., Bormotov, N.I., Balakhnin, S.M., and Serova, O.A., Pharm. Chem. J., 2005, vol.39, p.574. doi https://doi.org/10.1007/s11094-006-0023-9

    Article  CAS  Google Scholar 

  15. Takemura, M., Takashi, H., Kawakami, K., Takeshita, H., Kimura, Y., Watanabe, J., Sugimoto, Y., Kitamura, A., Nakajima, R., Kanai, K., and Fujisawa, T., Bioorg. Med. Chem. Lett., 2010, vol.20, p.3893.

    Article  CAS  PubMed  Google Scholar 

  16. Hammad, M., Mequid, A., Ananni, El-M., and Shafik, N., Egipt. J. Chem., 1987, vol.29, p.5401.

    Google Scholar 

  17. Ndakala, A.J., Gessner, R.K., Gitari, P.W., October, N., White, K.L., Hudson, A., Fakorede, F., Shackleford, D.M., Kaiser, M., Yeates, C., Charman, S.A., and Chibale, K., J. Med. Chem., 2011, vol.54, p.4581. doi https://doi.org/10.1021/jm200227r

    Article  CAS  PubMed  Google Scholar 

  18. Rida, S.M., Soliman, F.S.G., Badavey, El-S.A.M., Ghazzawi, El-E., Kader, O., and Kappe, T., J. Heterocycl. Chem., 1988, vol.25, p.1087.

    Article  CAS  Google Scholar 

  19. Badawey, El-S.A.M. and Kappe, C., Eur. J. Med. Chem., 1955, vol.30, p.327.

    Article  Google Scholar 

  20. Badawey, El-S.A.M. and Kappe, T., Eur. J. Med. Chem., 1999, vol.34, p.663.

    CAS  PubMed  Google Scholar 

  21. El-Hawash, S.A.M., Badawey, El-S.A.M., and Kappe, T., Pharmazie, 1999, vol.54, p.341.

    CAS  PubMed  Google Scholar 

  22. Ryzvanovich, G.A., Begunov, R.S., Rachinskaya, O.A., Muravenko, O.V., and Sokolov, A.A., Pharm. Chem. J., 2011, vol.45, p.141. doi https://doi.org/10.1007/s11094-011-0577-z

    Article  CAS  Google Scholar 

  23. Kachanov, A.V., Slabko, O.Yu., Baranova, O.V., Shilova, E.V., and Kaminskii, V.A., Tetrahedron Lett., 2004, vol.45, p.4461.

    Article  CAS  Google Scholar 

  24. Ganther, H.E. and Lawrence, J.R., Tetrahedron, 1997, vol.53, p.12299.

    Article  CAS  Google Scholar 

  25. Rao, C.V., Simi, B., Hirose, Y., Upadhyaya, P., Bayonmy, K., and Reddy, B.S., Int. J. Oncol., 2000, vol.16, p.519.

    CAS  PubMed  Google Scholar 

  26. Mugesh, G., du Mont, W.-W., and Sies, H., Chem. Rev., 2001, vol.101, p.2125.

    Article  CAS  PubMed  Google Scholar 

  27. Alekseev, V.I., Kaminskii, V.A., and Tilichenko, M.N., Chem. Heterocycl. Compd., 1975, vol.11, p.203. doi https://doi.org/10.1007/BF00471399

    Article  Google Scholar 

  28. Kaminskii, V.A., Slabko, O.Yu., and Tilichenko, M.N., Chem. Heterocycl. Compd., 1988, vol.24, p.648. doi https://doi.org/10.1007/BF00475601

    Article  Google Scholar 

  29. Slabko, O.Yu., Ageenko, N.V., Verbitskii, G.A., and Kaminski, V.A., Chem. Heterocycl. Compd., 2002, vol.38, p.226. doi https://doi.org/10.1023/A:1015351628312

    Article  CAS  Google Scholar 

  30. Fatiady, A.J., Synthesis, 1996, p.65.

    Google Scholar 

  31. Davies, K.E., Domany, G.E., Farhat, M., Herbert, J.A.L., Jefferson, A. M., Guttierres, M., and Suschitzky, H., J. Chem. Soc., Perkin Trans. 1, 1984, p.2465.

    Google Scholar 

  32. The Chemistry of the Quinonoid Compounds. Patai, S. and Rappoport, Z., Eds., Chichester: Wiley, 1974.

    Google Scholar 

  33. Kutyrev, A.A., Tetrahedron, 1991, vol.47, p.8043.

    Article  CAS  Google Scholar 

  34. Boder, D.L. and Zarrinmayeh, H., J. Org. Chem., 1990, vol.55, p.1379.

    Article  Google Scholar 

  35. Titov, E.A., Burmistrov, S.I., and Podobuev, G.A., Zh. Org. Khim., 1972, vol.8, p.821.

    Google Scholar 

  36. Bezverkhii, N.P. and Protashchuk, S.I., Zh. Org. Khim., 1986, vol.22, p.461.

    CAS  Google Scholar 

  37. Slabko, O.Yu., Britsina, O.I., and Kaminskii, V.A., Chem. Heterocycl. Compd., 1991, vol.27, p.788. doi https://doi.org/10.1007/BF00476215

    Article  Google Scholar 

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Authors and Affiliations

  1. Far Eastern Federal University, Universitetskii pr., o. Russkii, Vladivostok, 690902, Russia

    O. Yu. Slabko & V. A. Kaminskii

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  1. O. Yu. Slabko
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  2. V. A. Kaminskii
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Correspondence to O. Yu. Slabko.

Additional information

Russian Text © O.Yu. Slabko, V.A. Kaminskii, 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 2, pp. 198–207.

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Slabko, O.Y., Kaminskii, V.A. Synthesis of N-Arylquinone Diimine Derivatives of 2H-Benzimidazo[2,1-e]acridine and Their Reactions with Aromatic Amines. Russ J Org Chem 55, 152–160 (2019). https://doi.org/10.1134/S1070428019020052

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