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Synthesis of new hexahydro-5H-indolo[3,2-c]acridines and indolylbutanoic acids by Fischer cyclization of arylhydrazones

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Chemistry of Heterocyclic Compounds Aims and scope

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Arylhydrazones of 2,3,5,6,7,8-hexahydroacridin-4(1H)-ones and 7-amino-6-(arylhydrazono)-7-oxoheptanoic acids were cyclized by Fischer reaction, providing previously unknown polysubstituted indole derivatives. The starting hydrazones were synthesized under Japp–Klingemann reaction conditions by using 1,2,3,4,5,6,7,8-octahydroacridine-4-carboxamide and 2-oxocyclohexanecarboxamide as starting materials. It was established from the spectral data that the obtained 7-amino-6-(arylhydrazono)-7-oxoheptanoic acids existed as mixtures of (Z)- and (E)-isomers, but were converted to an individual (Z)- or (E)-isomer in DMSO solution.

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Notes

  1. Signals in counterphase.

References

  1. Bhat, V.; Dave, A.; MacKay, J. A.; Rawal, V. H. In The Alkaloids: Chemistry and Biology; Elsevier, 2014, Vol. 73, p. 65.

  2. Heravi, M. M.; Rohani, S.; Zadsirjan, V.; Zahedi, N. RSC Adv. 2017, 7, 52852.

    Article  CAS  Google Scholar 

  3. Park, N. I.; Kim, J. K.; Park, W. T.; Cho, J. W.; Lim, Y. P.; Park, S. U. Mol. Biol. Rep. 2010, 38, 4947.

    Article  Google Scholar 

  4. Wang, F.-Q.; Yang, H.; He, B.; Jia, Y.-K.; Meng, S.-Y.; Zhang, C.; Liu, H.-M.; Liu, F.-W. Tetrahedron 2016, 72, 5769.

    Article  CAS  Google Scholar 

  5. Haase, A. F.; Greiner, H. E.; Seyfried, C. A. Naunyn-Schmiedeberg's Arch. Pharmacol. 1991, 343, 588.

    Article  CAS  Google Scholar 

  6. Bartoszyk, G. D.; Hegenbart, R.; Ziegler, H. Eur. J. Pharmacol. 1997, 322, 147.

    Article  CAS  Google Scholar 

  7. Teng, X.; Degterev, A.; Jagtap, P.; Xing, X.; Choi, S.; Denu, R.; Yuan, J.; Cuny, G. D. Bioorg. Med. Chem. Lett. 2005, 15, 5039.

    Article  CAS  Google Scholar 

  8. Sundberg, R. J. Indoles; Academic Press: London, 1996.

    Google Scholar 

  9. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.

    Article  Google Scholar 

  10. Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 2001, 2491.

    Article  Google Scholar 

  11. Tokuyama, H. J. Synth. Org. Chem., Jpn. 2015, 73, 1120.

    Article  CAS  Google Scholar 

  12. Kotha, S.; Aswar, V. R.; Singhal, G. Tetrahedron 2017, 73, 6436.

    Article  CAS  Google Scholar 

  13. Park, J.; Kim, D.-H.; Das, T.; Cho, C.-G. Org. Lett. 2016, 18, 5098.

    Article  CAS  Google Scholar 

  14. Smith, J. M.; Moreno, J.; Boal, B. W.; Garg, N. K. J. Org. Chem. 2015, 80, 8954.

    Article  CAS  Google Scholar 

  15. Zaliznaya, E. V.; Farat, O. K.; Gorobets, N. Yu.; Markov, V. I.; Zubatyuk, R. I.; Mazepa, A. V.; Vashchenko, E. V. Chem. Heterocycl. Compd. 2015, 51, 327. [Khim. Geterotsikl. Soedin. 2015 , 51, 327.]

  16. Bouveault, L. Bull. Soc. Chim. Fr. 1893, 9, 368.

    Google Scholar 

  17. Kezdy F. J.; Jaz, J.; Bruylants, A. Bull. Soc. Chim. Belg. 1958, 67, 687.

    Article  CAS  Google Scholar 

  18. Wade, L. G., Jr.; Silvey, W. B. Org. Prep. Proced. Int. 1982, 14, 357.

    Article  CAS  Google Scholar 

  19. Sundberg, R. J. Indoles; Academic Press: London, 1996, p. 54.

    Google Scholar 

  20. Thummel, R. P.; Hegde, V. J. Org. Chem. 1989, 54, 1720.

    Article  CAS  Google Scholar 

  21. Pete, B.; Parlagh, G. Tetrahedron 2004, 60, 8829.

    Article  CAS  Google Scholar 

  22. Pete, B.; Tőke, L. Tetrahedron Lett. 2001, 42, 3373.

    Article  CAS  Google Scholar 

  23. Pete, B.; Parlagh, G. A. Tetrahedron Lett. 2003, 44, 2537.

    Article  CAS  Google Scholar 

  24. Heinrich, T.; Böttcher, H. Bioorg. Med. Chem. Lett. 2004, 14, 2681.

    Article  CAS  Google Scholar 

  25. Maas, G. In Encyclopedia of Reagents for Organic Synthesis; John Wiley and Sons, Inc., 2001, p. 1–4.

  26. Murphyt, W. H.; Jenkins, G. L. J. Am. Pharm. Assoc. 1943, 32, 83.

    Article  Google Scholar 

  27. Pete, B.; Varga, F.; Kovács, J. A. J. Heterocycl. Chem. 2004, 42, 615.

    Article  Google Scholar 

  28. Phillips, R.; Adams, R. Organic Reactions [Russian translation]; IL: Moscow, 1963, Vol. 10, p. 148.

  29. Ponticello, G. S.; Baldwin, J. J.; Lumma, P. K.; McClure, D. E. J. Org. Chem. 1980, 45, 4236.

    Article  CAS  Google Scholar 

  30. Bischoff, C.; Herma, H. J. Рrakt. Chem. 1976, 318, 773.

    Article  CAS  Google Scholar 

  31. Markov, V. I.; Farat, O. K. Chem. Heterocycl. Compd. 2012, 48, 925. [Khim. Geterotsikl. Soedin. 2012, 995.]

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The authors would like to express their gratitude to Candidate of Chemical Sciences N. E. Borisova for performing NMR experiments. NMR spectra were acquired at the Laboratory of Magnetic Tomography and Spectroscopy, Department of Chemistry, Moscow State University.

This work received financial support from the Ministry of Education and Science of Ukraine within the framework of the State budget item No. 0115U003159 “New synthetic methods for the design of nitrogen- and sulfur-containing biologically active compounds”.

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Authors and Affiliations

  1. Ukrainian State University of Chemical Technology, 8 Gagarina Ave., Dnipro, 49005, Ukraine

    Ekaterina V. Zaliznaya, Nikolai V. Smetanin, Svetlana A. Varenichenko & Victor I. Markov

  2. A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, 86 Lyustdorfska Road, Odessa, 65080, Ukraine

    Alexandr V. Mazepa

  3. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Oleg K. Farat

Authors
  1. Ekaterina V. Zaliznaya
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  2. Nikolai V. Smetanin
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  3. Svetlana A. Varenichenko
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  4. Alexandr V. Mazepa
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  5. Oleg K. Farat
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  6. Victor I. Markov
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Corresponding author

Correspondence to Ekaterina V. Zaliznaya.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(2), 138–145

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Zaliznaya, E.V., Smetanin, N.V., Varenichenko, S.A. et al. Synthesis of new hexahydro-5H-indolo[3,2-c]acridines and indolylbutanoic acids by Fischer cyclization of arylhydrazones. Chem Heterocycl Comp 54, 138–145 (2018). https://doi.org/10.1007/s10593-018-2245-7

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  • DOI: https://doi.org/10.1007/s10593-018-2245-7

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