Skip to main content
SpringerLink
Log in

Synthesis of 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed cyclization of indole-3-carbaldehyde oximes

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A new method for synthesizing 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed intramolecular electrophilic amination of 2-arylindole-3-carbaldehyde O-acetyl oximes was developed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A. Kumar, D. Kumar Ghosh, J. Ali, A. Ranjan, ACS Chem. Biol., 2019, 14, 901.

    Article  CAS  Google Scholar 

  2. M. van der Velden, A. Bilos, J. M. W. van den Heuvel, S. R. Rijpma, E. G. E. Hurkmans, R. W. Sauerwein, F. G. M. Russel, J. B. Koenderink, Malar. J., 2017, 16, 422.

    Article  Google Scholar 

  3. C. Borsari, R. Luciani, C. Pozzi, I. Poehner, S. Henrich, M. Trande, A. Cordeiro-da-Silva, N. Santarem, C. Baptista, A. Tait, F. Di Pisa, L. D. Iacono, G. Landi, S. Gul, M. Wolf, M. Kuzikov, B. Ellinger, J. Reinshagen, G. Witt, P. Gribbon, M. Kohler, O. Keminer, B. Behrens, L. Costantino, P. T. Nevado, E. Bifeld, J. Eick, J. Clos, J. Torrado, M. D. Jiménez-Antón, M. J. Corral, J. M Alunda, F. Pellati, R. C. Wade, S. Ferrari, S. Mangani, M. P. Costi, J. Med. Chem., 2016, 59, 7598.

    Article  CAS  Google Scholar 

  4. Z. H. Skraup, Ber. Dtsch. Chem. Ges., 1880, 13, 2086.

    Google Scholar 

  5. R. G. Gould, W.A. Jacobs, J. Am. Chem. Soc, 1939, 61, 2890.

    Article  CAS  Google Scholar 

  6. O. Doebner, Justus Liebigs Ann. Chem., 1887, 265.

  7. M. Conrad, L. Limpach, Ber. Dtsch. Chem. Ges., 1887, 20, 944.

    Article  Google Scholar 

  8. Q. Zhang, L. Zhang, C. Tang, H. Luo, X. Cai, Y. Chai, Tetrahedron, 2016, 72, 6935.

    Article  CAS  Google Scholar 

  9. H. Jiang, X. An, K. Tong, T. Zheng, Y. Zhang, S. Yu, Angew. Chem., Int. Ed., 2015, 54, 4055.

    Article  CAS  Google Scholar 

  10. R. J. Olsen, Tetrahedron Lett., 1991, 32, 5235.

    Article  CAS  Google Scholar 

  11. S. Buscemi, G. Cusmano, M. Gruttadauria, J. Heterocycl. Chem., 1990, 27, 861.

    Article  CAS  Google Scholar 

  12. W Verboom, P. J. S. S. Van Eijk, P. O. M. Conti, D. N. Reinhoudt, Tetrahedron, 1989, 45, 3131.

    Article  CAS  Google Scholar 

  13. J. Panteleev, R. Y. Huang, E. K. J. Lui, M. Lautens, Org. Lett., 2011, 13, 5314.

    Article  CAS  Google Scholar 

  14. T. Patra, S. Mukherjee, J. Ma, F Strieth-Kalthoff, F Glorius, Angew. Chem., Int. Ed., 2019, 58, 10514.

    Article  CAS  Google Scholar 

  15. X. Liu, Z. Qing, P. Cheng, X. Zheng, J. Zeng, H. Xie, Molecules, 2016, 21, 1690.

    Article  Google Scholar 

  16. R. T. McBurney, A. M. Z. Slawin, L. A. Smart, Y. Yua, J. C. Walton, Chem. Commun., 2011, 47, 7974.

    Article  CAS  Google Scholar 

  17. H. B. Zhao, P. Xu, J. Song, H. C. Xu, Angew. Chem., Lnt. Ed., 2018, 57, 15153.

    Article  CAS  Google Scholar 

  18. F Portela-Cubillo, J. S. Scott, J. C. Walton, J. Org. Chem., 2008, 73, 5558.

    Article  CAS  Google Scholar 

  19. K. Uchiyama, Y. Hayashi, K. Narasaka, Synlett, 1997, 445.

  20. T. D. Wahyuningsih, N. Kumar, D. StC Black, Tetrahedron, 2007, 63, 6713.

    Article  CAS  Google Scholar 

  21. K. A. Clayton, D. StC. Black, J. B. Harper, Tetrahedron, 2007, 63, 10615.

    Article  CAS  Google Scholar 

  22. L. He, H.-X. Chang, T.-C. Chou, N. Savaraj, C. C. Cheng, Eur. J. Med. Chem., 2003, 38, 101.

    Article  CAS  Google Scholar 

  23. L. N. Tumey, D. H. Boschelli, N. Bhagirath, J. Shim, E. A. Murphy, D. Goodwin, E. M. Bennett, M. Wang, L.-L. Lin, B. Press, M. Shen, R. K. Frisbie, P. Morgan, S. Mohan, Ju. Shin, V. R. Rao, Bioorg. Med. Chem. Lett., 2014, 24, 2066.

    Article  CAS  Google Scholar 

  24. O. N. Nadein, D. A. Aksenov, G. M. Abakarov, N. A. Aksenov, L. G. Voskressensky, A. V. Aksenov, Chem. Hetero cycl. Compd., 2019, 55, 905.

    CAS  Google Scholar 

  25. I. S. Antipin, M. A. Kazymova, M. A. Kuznetsov, A. V. Vasilyev, M. A. Ishchenko, A. A. Kiryushkin, L. M. Kuzne-tsova, S. V. Makarenko, V. A. Ostrovskii, M. L. Petrov, O. V. Solod, Yu. G. Trishin, I. P. Yakovlev, V. G. Nenaidenko, E. K. Beloglazkina, I. P. Beletskaya, Yu. A. Ustynyuk, P. A. Solov'ev, I. V. Ivanov, E. V. Malina, N. V. Sivova, V. V. Negrebetskii, Yu. I. Baukov, N. A. Pozharskaya, V. F. Traven', A. E. Shekotikhin, A. V. Varlamov, T. N. Borisova, Yu. A. Lesina, E. A. Krasnokutskaya, S. I. Rogozhnikov, S. N. Shurov, T. P. Kustova, M. V. Klyuev, O. G. Khelevina, P. A. Stuzhin, A. Yu. Fedorov, A. V. Gushchin, V. A. Dodonov, A. V. Kolobov, V. V. Plakhtinskii, Yu. V. Orlov, A. P. Kriven'ko, O. V. Fedotova, N. V. Pchelintseva, V. N. Charushin, O. N. Chupakhin, Yu. N. Klimochkin, A. Yu. Klimochkina, V. N. Kuryatnikov, Yu. A. Malinovskaya, A. S. Levina, O. E. Zhu-ravlev, L. I. Voronchikhina, A. S. Fisyuk, A. V. Aksenov, N. A. Aksenov, I. V. Aksenova, Russ. J. Org. Chem., 2017, 53, 1275.

    Article  Google Scholar 

  26. 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. Shmigol', 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. Maslennikova, 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 

  27. A. V. Aksenov, D. A. Aksenov, N. A. Orazova, N. A. Aksenov, G. D. Griaznov, A. De Carvalho, R. Kiss, V. Mathieu, A. Kornienko, M. Rubin, J. Org. Chem., 2017, 82, 3011.

    Article  CAS  Google Scholar 

  28. N. A. Aksenov, A. V. Aksenov, A. Kornienko, A. De Carvalho, V. Mathieu, D. A. Aksenov, S.N. Ovcharov, G. D. Griaznov, M. Rubin, RSC Adv., 2018, 8, 36980.

    Article  CAS  Google Scholar 

  29. A. V. Aksenov, D. A. Aksenov, G. D. Griaznov, N. A. Aksenov, L. G. Voskressensky, M. Rubin, Org. Biomol. Chem., 2018, 16, 4325.

    Article  CAS  Google Scholar 

  30. N. A. Aksenov, A. Z. Gasanova, G. M. Abakarov, I. V. Aksenova, A. V. Aksenov, Russ. Chem. Bull., 2019, 68, 836.

    Article  CAS  Google Scholar 

  31. R. Alonso, A. Caballero, P. J. Campos, M. A. Rodriguez, Tetrahedron, 66, 2010, 8828.

    Article  CAS  Google Scholar 

  32. M. G. Uchuskin, A. S. Pilipenko, O. V. Serdyuk, I. V. Trushkov, A. V. Butin, Org. Biomol. Chem., 2012, 10, 7262.

    Article  CAS  Google Scholar 

  33. Z. Bakherad, M. Safavi, A. Fassihi, H. Sadeghi-Aliabadi, M. Bakherad, H. Rastegar, J. B. Ghasemi, S. Sepehri, L. Saghaie, M. Mahdavi, Res. Chem. Intermed., 2019, 45, 2827.

    Article  CAS  Google Scholar 

  34. Y. Bazile, P. De Cointet, C. Pigerol, J. Heterocycl. Chem., 1978, 15, 859.

    Article  CAS  Google Scholar 

  35. A. R. Saundane, V. Tukaram Katkar, A. V. Vaijinath, J. Chem., 2013, 1.

  36. J. A. Weisbach, E. Macko, N. J. De Sanctis, M. P. Cava, B. Douglas, J. Med. Chem., 1964, 7, 735.

    Article  CAS  Google Scholar 

  37. B. Corbel, F. Michaud, L. Meijer, G. Simon, H. Couthon-Gourves, J. Haelters, N. Kervarec, J. Heterocycl. Chem., 2007, 44, 793.

    Article  Google Scholar 

  38. K. C. Coffman, T. A. Palazzo, T. P. Hartley, J. C. Fettinger, D. J. Tantillo, M. J. Kurth, Org. Lett., 2013, 15, 2062.

    Article  CAS  Google Scholar 

  39. V. N. Pathak, M. Jain, A. Tiwari, Org. Prep. Proc. Int., 2008, 40, 493.

    Article  CAS  Google Scholar 

  40. J. Qu, N. Kumar, M. Alamgir, D. StC. Black, Tetrahedron Lett, 2009, 50, 5628.

    Article  CAS  Google Scholar 

  41. L. R. Whittell, K. T. Batty, R. P. M. Wong, E. M. Bolitho, S. A. Fox, T. M. E. Davis, P. E. Murray, Bioorg. Med. Chem., 2011, 19, 7519.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. North Caucasus Federal University, 1 A ul. Pushkina, 355017, Stavropol, Russian Federation

    N. A. Aksenov, A. Z. Gasanova, F. Yu. Prokonov, D. A. Aksenov & A. V. Aksenov

  2. Dagestan State Fechnical University, 70 prosp. Imam Shamil, 367010, Makhachkala, Russian Federation

    G. M. Abakarov

Authors
  1. N. A. Aksenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Z. Gasanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. F. Yu. Prokonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. A. Aksenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. M. Abakarov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. V. Aksenov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. A. Aksenov.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 17-73-10301) and the Council on Grants at the President of the Russian Federation (Program for the State Support of Young Russian Scientists, Grant MK-3089.2018.3).

Based on the materials of the 4th Russian Conference on Medicinal Chemistry with International participation (June 9–14, 2019, Ekaterinburg, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2262–2270, December, 2019.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Aksenov, N.A., Gasanova, A.Z., Prokonov, F.Y. et al. Synthesis of 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed cyclization of indole-3-carbaldehyde oximes. Russ Chem Bull 68, 2262–2270 (2019). https://doi.org/10.1007/s11172-019-2697-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-019-2697-7

Key words

Search

Navigation