Skip to main content
SpringerLink
Log in

A New Method for the Synthesis of Substituted 8,9,10,11-Tetrahydroindolo[1,2-a]Quinoxalin-6(5H)-Ones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 1-(cyclohexen-1-yl)pyrrolidines with 3-(α-chlorobenzyl)quinoxalin-2(1H)-ones resulted in the formation of 8,9,10,11-tetrahydroindolo[1,2-a]quinoxalin-6(5H)-ones via a tandem sequence of Stork enamine alkylation and intramolecular annulation. Oxidative dehydrogenation gave indolo[1,2-a]quinoxalin-6(5H)-one.

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

Figure 1
Figure 2
Figure 3

Similar content being viewed by others

Notes

  1. Signal of the minor isomer.

References

  1. (a) Mamedov, V. A. Quinoxalines. Synthesis, Reactions, Mechanisms and Structure; Springer International Publishing, 2016. (b) The Chemistry of Heterocyclic Сompounds: Condensed Pyrazines; Cheeseman, G. W. H.; Cookson, R. F., Eds.; John Wiley & Sons: New York, 1979, Vol. 35.

  2. (a) Alleca, S.; Corona, P.; Lorigo, M.; Paglietti, G.; Loddo, R.; Mascia, V.; Busonera, B.; La Colla, P. Farmaco 2003, 58, 639. (b) Patel, M.; Mc Hugh, R. J.; Cordova, B. C.; Klabe, R. M.; Erickson-Vitanen, S.; Trainor, G. L.; Rodgers, J. D. Bioorg. Med. Chem. Lett. 2000, 10, 1729. (c) Guillon, J.; Dallemagne, P.; Pfeiffer, B.; Renard, P.; Manechez, D.; Kervran, A.; Rault, S. Eur. J. Med. Chem. 1998, 33, 293. (d) Kim, K. S.; Qian, L.; Bird, J. E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. J. Med. Chem. 1993, 36, 2335.

  3. (a) Jacobsen, E. J.; Stelzer, L. S.; Belonga, K. L.; Carter, D. B.; Im, W. B.; Sethy, V. H.; Tang, A. H.; VonVoigtlander, P. F.; Petke, J. D. J. Med. Chem. 1996, 39, 3820. (b) Davey, D. D.; Erhardt, P. W.; Cantor, E. H.; Greenberg, S. S.; Ingebretsen, W. R.; Wiggins, J. J. Med. Chem. 1991, 34, 2671. (c) Colotta, V.; Cecchi, L.; Catarzi, D.; Filacchioini, G.; Martini, C.; Tacchi, P.; Lucacchini, A. Eur. J. Med. Chem. 1995, 30, 133.

  4. (a) Sakata, G.; Makino, K.; Kurasawa, Y. Heterocycles 1988, 27, 2481. (b) Seitz, L. E.; Suling, W. J.; Reynolds, R. C. J. Med. Chem. 2002, 45, 5604. (c) Gazit, A.; App, H.; McMahon, G.; Chen, J.; Levitzki, A.; Bohmer, F. D. J. Med. Chem. 1996, 39, 2170. (d) Ali, M. M.; Ismail, M. M. F.; El-Gaby, M. S. A.; Zahran, M. A.; Ammar, Y. A. Molecules 2000, 5, 864. (e) Campiani, G.; Nacci, V.; Corelli, F.; Anzini, M. Synth. Commun. 1991, 21, 1567. (f) Kher, S. S.; Penzo, M.; Fulle, S.; Ebejer, J. P.; Finn, P. W.; Blackman, M. J.; Jirgensons, A. Chem. Heterocycl. Compd. 2015, 50, 1457. [Khim. Geterotsikl. Soedin. 2014, 1583.]

  5. (a) Mamedov, V. A.; Kalinin, A. A. Chem. Heterocycl. Compd. 2010, 46, 641. [Khim. Geterotsikl. Soedin. 2010, 803.] (b) Kalinin, A. A.; Mamedov, V. A. Chem. Heterocycl. Compd. 2011, 46, 1423. [Khim. Geterotsikl. Soedin. 2010, 1763.]

  6. Mamedov, V. A.; Zhukova, N. A. In Progress in Heterocyclic Chemistry; Gribble, G. W.; Joule, J. A., Ed.; Elsevier: Oxford, 2012, Vol. 24, p. 55.

  7. Mamedov, V. A.; Zhukova, N. A. In Progress in Heterocyclic Chemistry; Gribble, G. W.; Joule, J. A., Ed.; Elsevier: Oxford, 2013, Vol. 25, p. 1.

  8. Corona, P.; Vitale, G.; Loriga, M.; Paglietti, G.; La Colla, P.; Collu, G.; Sanna, G.; Loddo, R. Eur. J. Med. Chem. 2006, 41, 1102.

    Article  CAS  Google Scholar 

  9. (а) Mamedov, V. A.; Kalinin, A. A. Russ. Chem. Rev. 2014, 83, 820. [Usp. Khim. 2014, 83, 820.] (b) Mamedov, V. A.; Kalinin, A. A., Balandina A. A., Rizvanov, I. Kh.; Latypov, Sh. K. Tetrahedron 2009, 65, 9412. (c) Kalinin, A. A.; Voloshina, A. D.; Kulik, N. V.; Zobov, V. V.; Mamedov, V. A. Eur. J. Med. Chem. 2013, 66, 345.

  10. (а) Somei, M.; Yamada, F. Nat. Prod. Rep. 2003, 20, 216. (b) Gupta, L.; Talwar, A.; Chauhan, P. M. S. Curr. Med. Chem. 2007, 14, 1789.

  11. (а) Xu, H.; Lv, M. Curr. Pharm. Des. 2009, 15, 2120. (b) Ran, J. Q.; Huang, N.; Xu, H.; Yang, L. M.; Lv, M.; Zheng, Y. T. Bioorg. Med. Chem. Lett. 2010, 20, 3534. (c) Williams, J. D.; Chen, J. J.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 2004, 47, 5753.

  12. (а) Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Landi, L.; Prata, C.; Berridge, M. V.; Grasso, C.; Fiebig, H. H.; Kelter, G.; Burger, A. M.; Kunkel, M. W. J. Med. Chem. 2008, 51, 4563. (b) Mahboobi, S.; Sellmer, A.; Eichhorn, E.; Beckers, T.; Fiebig, H. H.; Kelter, G. Eur. J. Med. Chem. 2005, 40, 85. (с) Girgis, A. S. Eur. J. Med. Chem. 2009, 44, 1257.

  13. Mathada, B. S. D.; Mathada, M. B. H. Chem. Pharm. Bull. 2009, 57, 557.

    Article  CAS  Google Scholar 

  14. (а) Bhati, S. K.; Kumar, A. Eur. J. Med. Chem. 2008, 43, 2323. (b) Fakhr, I. M. I.; Radwan, M. A. A.; El-Batran, S.; Abd El-Salam, O. M. E.; El-Shenawy, S. M. Eur. J. Med. Chem. 2009, 44, 1718.

  15. (а) Xu, H.; Fan, L. L. Eur. J. Med. Chem. 2011, 46, 1919. (b) Verma, A. K.; Jha, R. R.; Sankar, V. K.; Aggarwal, T.; Singh, R. P.; Chandra, R. Eur. J. Org. Chem. 2011, 6998. (c) Agarwal, P. K.; Sawant, D.; Sharma, S.; Kundu, B. Eur. J. Org. Chem. 2009, 292. (d) Lin, P. T; Salunke, D. B.; Chen, L. H.; Sun, C. M. Org. Biomol. Chem. 2011, 9, 2925. (e) Sokolova, E. A; Festa, A. A. Chem. Heterocycl. Compd. 2016, 52, 219. [Khim. Geterotsikl. Soedin. 2016, 52, 219.]

  16. (а) Maiti, B.; Sun, C. M. New J. Chem. 2011, 35, 1385. (b) Lai, J. J.; Salunke, D. B.; Sun, C. M. Org. Lett. 2010, 12, 2174.

  17. Fan, Y. S.; Jiang, Y. J.; An, D.; Sha, D.; Antilla, J. C.; Zhang, S. Org. Lett. 2014, 16, 6112.

    Article  CAS  Google Scholar 

  18. Wang, L.; Guo, W.; Zhang, X. X.; Xia, X. D.; Xiao, W. D. Org. Lett. 2012, 14, 740.

    Article  CAS  Google Scholar 

  19. (а) Yi, C. S.; Yun, S. Y. J. Am. Chem. Soc. 2005, 127, 17000. (b) Patil, N. T.; Lakshmi, P. G. V. V.; Singh, V. Eur. J. Org. Chem. 2010, 4719.

  20. (а) Zhou, Y.; Ji, X.; Liu, G.; Zhang, D.; Zhao, L.; Jiang, H.; Liua, H. Adv. Synth. Catal. 2010, 352, 1711. (b) Patil, N. T.; Kavthe, R. D.; Shinde, V. S.; Sridhar, B. J. Org. Chem. 2010, 75, 3371.

  21. (а) Rustagi, V.; Tiwari, R.; Verma, A. K. Eur. J. Org. Chem. 2012, 4590. (b) Rustagi, V.; Aggarwal, T.; Verma, A. K. Green Chem. 2011, 13, 1640.

  22. (а) Luo, X.; Chenard, E.; Martens, P.; Cheng, Y. X.; Tomaszewski, M. J. Org. Lett. 2010, 12, 3574. (b) Abbiati, G.; Beccalli, E. M.; Broggini, G.; Paladino, G,; Rossia, E. Synthesis 2005, 2881.

  23. (а) Maddirala, S. J.; Basanagoudar, L. D. Synth. Commun. 2003, 33, 851. (b) Beach, M. J.; Hope, R.; Klaubert, D. H.; Russel R. K. Synth. Commun. 1995, 25, 2165. (с) Yuan, Q.; Ma, D. J. Org. Chem. 2008, 73, 5159.

  24. Huang, A.; Liu, F.; Zhan, C.; Liu Y.; Ma, C. Org. Biomol. Chem. 2011, 9, 7351.

    Article  CAS  Google Scholar 

  25. (a) Biswas, S.; Singh, V.; Batra, S. Tetrahedron 2010, 66, 7781. (b) Zhao, F.; Zhang, L.; Liu, H.; Zhou, S.; Liu, H. Beilstein J. Org. Chem. 2013, 9, 2463.

  26. Chicharro, R.; Castro, S.; Reino, J. L.; Arán, V. J. Eur. J. Org. Chem. 2003, 2314.

  27. Samala, S.; Arigela, R. K.; Kant, R.; Kundu, B. J. Org. Chem. 2014, 79, 2491.

    Article  CAS  Google Scholar 

  28. Shvedov, V. I.; Altukhova, L. B.; Alekseev, V. V.; Grinev, A. N. Chem. Heterocycl. Compd. 1970, 6, 1255. [Khim. Geterotsikl. Soedin. 1970, 1348.]

  29. Atfah, A.; Abu-Shuheil, M. Y.; Hill, J. Tetrahedron 1990, 46, 6483.

    Article  CAS  Google Scholar 

  30. (a) Mamedov, V. A.; Kalinin, A. A.; Gubaidullin, A. T.; Nurkhametova, I. Z.; Litvinov, I. A.; Levin, Ya. A. Chem. Heterocycl. Compd. 1999, 35, 1459. [Khim. Geterotsikl. Soedin. 1999, 1664.] (b) Mamedov, V. A.; Zhukova, N. A.; Balandina, A. А.; Kharlamov, S. V.; Beschastnova, T. N.; Rizvanov, I. Kh.; Latypov, Sh. K. Tetrahedron 2012, 68, 7363.

  31. (a) Mamedov, V. A.; Nuretdinov, I. A.; Sibgatullina, F. G. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1989, 38, 1292. [Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 1412.] (b) Saifina, D. F.; Ganieva, V. R.; Mamedov, V. A. Russ. J. Org. Chem. 2009, 45, 1244. [Zh. Org. Khim. 2009, 45, 1252.] (c) Kalinin, A. A.; Mamedov, V. A. Chem. Heterocycl. Compd. 2004, 40, 129. [Khim. Geterotsikl. Soedin. 2004, 133.] (d) Mamedov, V. A.; Kalinin, A. A.; Azancheev, N. M.; Levin, Ya. A. Russ. J. Org. Chem. 2003, 39, 125. [Zh. Org. Khim. 2003, 39, 135.]

  32. (a) Bagal, S. K.; Adlington, R. M.; Baldwin, J. E.; Marquez, R. J. Org. Chem. 2004, 69, 9100. (b) Maiti, S.; Achari, B.; Mukhopadhyay, R.; Banerjee, A. K. J. Chem. Soc., Perkin Trans. 1 2002, 1769. (c) McNally, J. J.; Youngman, M. A.; Lovenberg, T. W.; Nepomuceno, D. H.; Wilson, S. J.; Dax, S. L. Bioorg. Med. Chem. Lett. 2000, 10, 213.

  33. (a) Overman, L. E.; Wolfe, J. P. J. Org. Chem. 2002, 67, 6421. (b) Mitschke, U.; Osteritz, E. M.; Debaerdemaeker, T.; Sokolowski, M.; Bauerle, P. Chem.–Eur. J. 1998, 4, 2211. (c) Ma, Li-J., Inokuchi, T. Chem. Commun. 2010, 46, 7037.

  34. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

  35. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32(4), 837.

  36. APEX (Version 2.1). SAINTPlus. Data Reduction and Correction Program. Version 7.31A. Bruker Advansed X-Ray Solutions; BrukerXS Inc.: Madison, 2006.

    Google Scholar 

  37. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7.

    Article  CAS  Google Scholar 

Download references

This work received financial support from the Russian Science Foundation (project No. 14-23-00073-p).

Author information

Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 Akademika Arbuzova St, Kazan, 420088, Republic of Tatarstan, Russia

    Vakhid A. Mamedov, Elena A. Khafizova, Anastasiya I. Zamaletdinova, Julia K. Voronina, Saniya F. Kadyrova, Ekaterina V. Mironova, Dmitry B. Krivolapov, Ildar Kh. Rizvanov & Oleg G. Sinyashin

  2. Kazan National Research Technological University, 68 Karla Marksa St, Kazan, 420015, Republic of Tatarstan, Russia

    Vakhid A. Mamedov, Elena A. Khafizova, Anastasiya I. Zamaletdinova & Oleg G. Sinyashin

Authors
  1. Vakhid A. Mamedov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elena A. Khafizova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Anastasiya I. Zamaletdinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Julia K. Voronina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Saniya F. Kadyrova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ekaterina V. Mironova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Dmitry B. Krivolapov
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Ildar Kh. Rizvanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Oleg G. Sinyashin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vakhid A. Mamedov.

Additional information

Supplementary information file containing X-ray crystallography data for compounds 3a,d–f,h,i is available from the journal website at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, Submitted December 20, 2016 2017, 53(5), 560–567

Electronic supplementary material

ESM 1

(PDF 404 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mamedov, V.A., Khafizova, E.A., Zamaletdinova, A.I. et al. A New Method for the Synthesis of Substituted 8,9,10,11-Tetrahydroindolo[1,2-a]Quinoxalin-6(5H)-Ones. Chem Heterocycl Comp 53, 560–567 (2017). https://doi.org/10.1007/s10593-017-2090-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2090-0

Keywords

Search

Navigation