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Rearrangement in the systems ethyl bromopyruvate-1-(cyclohex-1-enyl)piperidine, -pyrrolidine, and -morpholine as an effi cient approach to 4,5,6,7-tetrahydroindoles

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Abstract

1-(Cyclohex-1-enyl)piperidine, -pyrrolidine, and -morpholine react with ethyl bromopyruvate in refluxing dioxane to afford the corresponding 4,5,6,7-tetrahydroindole derivatives. Possibility to convert the synthesized compounds into their aromatic counterparts was exemplified by one model compound.

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References

  1. C. F. Masaguer, E. Ravina, Tetrahedron Lett., 1996, 37, 5171.

    Article  CAS  Google Scholar 

  2. W. A. Remers, M. J. Weiss, J. Org. Chem., 1965, 30, 5232.

    Google Scholar 

  3. L. Chacon-Garcia, R. Martinez, Eur. J. Med. Chem., 2002, 37, 261.

    Article  CAS  PubMed  Google Scholar 

  4. L. Chunchatprasert, P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1996, 1787.

    Google Scholar 

  5. A. Fluxe, S. Wu, J. B. Shefer, J. M. Janusz, M. Murawsky, G. M. Fadayel, B. Fang, M. Hare, L. Djandjighian, Bioorg. Med. Chem. Lett., 2006, 16, 5855.

    Article  CAS  PubMed  Google Scholar 

  6. C. L. Sha. er, M. Gunduz, T.N. O’Connell, R. S. Obach, S. Yee, Drug Metab. Dispos., 2005, 33, 1688.

    Article  CAS  Google Scholar 

  7. L. Sun, N. Tran, C. Liang, S. Hubbard, F. Tang, K. Lipson, R. Schreck, Y. Zhou, G. McMahon, C. Tang, J. Med. Chem., 2000, 43, 2655.

    Article  CAS  PubMed  Google Scholar 

  8. S. Naruto, J. Sugano, Y. Ueda, T. Kaneko, Y. Kumagai, Jpn. Koka. Tokky. Koho, Jp.07133274A 19950523; Chem. Abstr., 1995, 123, 285770..

    Google Scholar 

  9. W. A. Remers, R. H. Roth, M. J. J. Weiss, Med. Chem., 1971, 14, 860.

    Article  CAS  Google Scholar 

  10. W. A. Remers, R. H. Roth, G. J. Gibs, M. J. Weiss, J. Org. Chem., 1971, 36, 1232.

    Article  CAS  Google Scholar 

  11. C. C. McComas, D. L. Va. Vranken, Tetrahedron Lett., 1999, 40, 8039.

    Article  CAS  Google Scholar 

  12. A. L. Sigan, D. V. Gusev, N. D. Chkanikov, E. Y. Shmidt, A. V. Ivanov, A. I. Mihaleva, Tetrahedron Lett., 2011, 52, 5025.

    Article  CAS  Google Scholar 

  13. M. L. Rosenberg, J. H. F. Aasheim, M. Trebbin, E. Uggerud, T. Hansen, Tetrahedron Lett., 2009, 50, 6506.

    Article  CAS  Google Scholar 

  14. E. D. Edstrom, Synlett, 1995, 49.

    Google Scholar 

  15. D. R. Hutchison, N. K. Nayyar, M. J. Martinelli, Tetrahedron Lett., 1996, 37, 2887.

    Article  CAS  Google Scholar 

  16. N. K. Nayyar, D. R. Hutchison, M. J. Martinelli, J. Org. Chem., 1997, 62, 982.

    Article  CAS  Google Scholar 

  17. Y. Aoyagi, T. Mizusaki, M. Shishikura, T. Komine, T. Yoshi-naga, H. Inaba, A. Ohta, K. Takeya, Tetrahedron, 2006, 62, 8533.

    Article  CAS  Google Scholar 

  18. E. Bellur, P. Langer, Tetrahedron Lett., 2006, 47, 2151.

    Article  CAS  Google Scholar 

  19. H. M. C. Ferraz, F. L. C. Pereira, F. S. Leite, Tetrahedron, 1999, 55, 10915.

    Article  CAS  Google Scholar 

  20. L. Piras, C. Ghiron, G. Minetto, M. Taddei, Tetrahedron Lett., 2008, 49, 459.

    Article  CAS  Google Scholar 

  21. M. Matsumoto, N. Watanabe, Heterocycles, 1984, 22, 2313.

    Article  CAS  Google Scholar 

  22. L. Xia, Y. R. Lee, Adv. Synth. Catal., 2013, 355, 2361.

    Article  CAS  Google Scholar 

  23. R. Martínez, J. G. Avila, M. T. Ramírez, A. Perez, A. Martínez, Bioorg. Med. Chem., 2006, 14, 4007.

    Article  CAS  PubMed  Google Scholar 

  24. I.-S. H. Lee, M. J. Kwon, C. K. Lee, Bull. Korean Chem. Soc., 2012, 33, 341.

    Article  CAS  Google Scholar 

  25. Y. Wang, X. Bi, D. Li, P. Liao, Y. Wang, J. Yang, Q. Zhang, Q. Liu, Chem. Commun., 2011, 809.

    Google Scholar 

  26. P. Barraja, P. Diana, A. Montalbano, A. Carbone, G. Cirrin-cione, G. Viola, A. Salvador, D. Vedaldi, F. Dall’Acqua, Bioorg. Med. Chem., 2008, 16, 9668.

    Article  CAS  PubMed  Google Scholar 

  27. V. A. Mamedov, T. N. Beschastnova, N. A. Zhukova, A. T. Gubaidullin, R. A. Isanov, I. Kh. Rizvanov, Tetrahedron Lett., 2008, 49, 4658.

    Article  CAS  Google Scholar 

  28. V. A. Mamedov, E. A. Haf. zova, A. I. Zamaletdinova, I. Kh. Rizvanov, A. B. Mirgorodskaya, L. Ya. Zakharova, Sh. K. Latypov, O. G. Sinyashin, Tetrahedron, 2015, 71, 9143.

    Article  CAS  Google Scholar 

  29. A. I. Konovalov, I. S. Antipin, V. A. Burilov, T. I. Madzhidov, A. R. Kurbangalieva, A. V. Nemtarev, S. E. Solovieva, I. I. Stoikov, V. A. Mamedov, L. Ya. Zakharova, E. L. Gavrilova, O. G. Sinyashin, I. A. Balova, A. V. Vasilyev, I. G. Zenkevich, M. Yu. Krasavin, M. A. Kuznetsov, A. P. Molchanov, M. S. Novikov, V. A. Nikolaev, L. L. Rodina, A. F. Khlebnikov, I. P. Beletskaya, S. Z. Vatsadze, S. P. Gromov, N. V. Zyk, A. T. Lebedev, D. A. Lemenovskii, V. S. Petrosyan, V. G. Nenaidenko, V. V. Negrebetskii, Yu. I. Baukov, T. A. Shmi-gol’, A. A. Korlyukov, A. S. Tikhomirov, A. E. Shchekotikhin, V. F. Traven’, L. G. Voskresenskii, F. I. Zubkov, O. A. Golubchikov, A. S. Semeikin, D. B. Berezin, P. A. Stuzhin, V. D. Filimonov, E. A. Krasnokutskaya, A. Yu. Fedorov, A. V. Nyuchev, V. Yu. Orlov, R. S. Begunov, A. I. Rusakov, A. V. Kolobov, E. R. Kofanov, O. V. Fedotova, A. Yu. Egorova, V. N. Charushin, O. N. Chupakhin, Yu. N. Klimochkin, V. A. Osyanin, A. N. Reznikov, A. S. Fisyuk, G. P. Sagitullina, A. V. Aksenov, N. A. Aksenov, M. K. Grachev, V. I. Maslen-nikova, M. P. Koroteev, A. K. Brel’, S. V. Lisina, S. M. Medvedeva, Kh. S. Shikhaliev, G. A. Suboch, M. S. Tovbis, L. M. Mironovich, S. M. Ivanov, S. V. Kurbatov, M. E. Kletskii, O. N. Burov, K.I. Kobrakov, D. N. Kuznetsov, Russ. J. Org. Chem., 2018, 54, 157.

    Article  CAS  Google Scholar 

  30. V. A. Mamedov, E. A. Khafizova, A. I. Zamaletdinova, J. K. Voronina, S. F. Kadyrova, E. V. Mironova, D. B. Krivolapov, I. Kh. Rizvanov, O. G. Sinyashin, Chem. Heterocycl. Compd., 2017, 53, 560.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences,”, 8 ul. Arbuzova, 420088, Kazan, Russian Federation

    V. A. Mamedov, A. I. Zamaletdinova, V. V. Syakaev, E. A. Khafizova, Sh. K. Latypov & O. G. Sinyashin

  2. Kazan National Research Technological University, 68 ul. Karl Marx, 420015, Kazan, Russian Federation

    V. A. Mamedov, A. I. Zamaletdinova & O. G. Sinyashin

Authors
  1. V. A. Mamedov
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  2. A. I. Zamaletdinova
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  3. V. V. Syakaev
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  4. E. A. Khafizova
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  5. Sh. K. Latypov
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  6. O. G. Sinyashin
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Correspondence to V. A. Mamedov.

Additional information

Based on the materials of the Conference “Modern Trends in Chemistry, Biology, and Medicine: from Molecule to Drug” (November 26–28, 2018, Kazan, Russia)

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1014–1019, May, 2019.

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Mamedov, V.A., Zamaletdinova, A.I., Syakaev, V.V. et al. Rearrangement in the systems ethyl bromopyruvate-1-(cyclohex-1-enyl)piperidine, -pyrrolidine, and -morpholine as an effi cient approach to 4,5,6,7-tetrahydroindoles. Russ Chem Bull 68, 1014–1019 (2019). https://doi.org/10.1007/s11172-019-2512-5

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  • DOI: https://doi.org/10.1007/s11172-019-2512-5

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