Skip to main content
SpringerLink
Log in

[C8dabco]Br: a mild and convenient catalyst for intramolecular cyclization of 2-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A new and convenient synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones has been described using the intramolecular cyclization of 2-aminochalcones catalyzed by 1-octyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide ([C8dabco]Br). Recyclability of the catalyst, high yields, simple isolation of the products, and high atom economy are the noteworthy aspects of the protocol.

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

Similar content being viewed by others

References

  1. (a) Shimokororiyama, M. In The Chemistry of Flavonoid Compounds; Geissaman, T. A., Ed.; Pergamon Press: NewYork, 1962, p. 286. (b) Harborne, J. B.; Williams, C. A. Nat. Prod. Rep. 1995, 12, 639.

  2. Kalinin, V. N.; Shostakovskii, M. V.; Ponomarev, A. B. Tetrahedron Lett. 1992, 33, 373.

    Article  CAS  Google Scholar 

  3. (a) The Flavonoids. Advances in Research Since 1980; Harborne, J. B., Ed.; Chapman and Hall: New York, 1988. (b) Flavonoids: Chemistry, Biochemistry and Applications; Andersen, Ø. M.; Markham, K. R., Eds.; Taylor & Francis Ltd.: London, 2006. (c) Chang, L. C.; Kinghorn, A. D. In Bioactive Compounds from Natural Sources: Isolation, Characterization and Biological Properties; Tringali, C., Ed.; Taylor & Francis Ltd.: London, 2001, p. 159.

  4. (a) Xia, Y.; Yang, Z.-Y.; Xia, P.; Bastow, K. F.; Tachibana, Y.; Kuo, S.-C.; Hamel, E.; Hackl, T.; Lee, K.-H. J. Med .Chem. 1998, 41, 1155. (b) Laliberte, R.; Campbell, D. J.; Bruderlein, F. Can. J. Pharm. Sci. 1967, 2, 37.

  5. Li, L.; Wang, H. K.; Kuo, S. C.; Wu, T. S.; Lednicer, D.; Lin, C.; Hamel, E.; Lee, K. H. J. Med. Chem. 1994, 37, 3400.

    Article  CAS  Google Scholar 

  6. Xia, Y.; Yang, Z.-Y.; Xia, P.; Bastow, K. F.; Nakanishi, Y.; Lee, K.-H. Bioorg. Med. Chem. Lett. 2000, 10, 699.

    Article  CAS  Google Scholar 

  7. Gao, F.; Johnson, K. F.; Schlenoff, J. B. J. Chem. Soc., Perkin Trans. 2 1996, 269.

  8. (a) Xia, Y.; Yang, Z. Y.; Xia, P.; Bastow, K. F.; Tachibana, Y.; Kuo, S. C.; Hamel, E.; Hackl, T.; Lee, K. H. J. Med. Chem. 1998, 41, 1155. (b) Huang, L. J.; Hsieh, M. C.; Teng, C. M.; Lee, K. H.; Kuo, S. C. Bioorg. Med. Chem. 1998, 6, 1657. (c) Ko, T. C.; Hour, M. J.; Lien, J. C.; Teng, C. M.; Lee, K. H.; Kuo, S. C.; Huang, L. J. Bioorg. Med. Chem. 2001, 11, 279. (d) Xia, Y.; Yang, Z. Y.; Xia, P.; Hackl, T.; Hamel, E.; Mauger, A.; Wu, J. H.; Lee, K. H. J. Med. Chem. 2001, 44, 3932. (e) Xia, Y.; Yang, Z. Y.; Xia, P.; Hackl, T.; Hamel, E.; Mauger, A.; Wu, J. H.; Lee, K. H. Bioorg. Med. Chem. Lett. 2003, 13, 2891. (f) Hadjeri, M.; Peiller, E. L.; Beney, C.; Deka, N.; Lawson, M. A.; Dumontet, C.; Boumendjel, A. J. Med. Chem. 2004, 47, 4964. (g) Lai, Y. Y.; Huang, L. J.; Lee, K. H.; Xiao, Z.; Bastow, K. F.; Yamori, T.; Kuo, S. C. Bioorg. Med. Chem. 2005, 13, 265.

  9. (a) Donnelly, J. A.; Farrell, D. F. Tetrahedron 1990, 46, 885. (b) Tokes, A. L.; Litkei, G. Synth. Commun. 1993, 23, 895. (d) Tokes, A. L.; Janzso, G. Synth. Commun. 1989, 19, 3159.

  10. Donnelly, J. A.; Farrell, D. F. J. Org. Chem. 1990, 55, 1757.

    Article  CAS  Google Scholar 

  11. Patonay, T.; Litkei, G.; Zsuga, M.; Kiss, A. Org. Prep. Proced. 1984, 16, 315.

    Article  CAS  Google Scholar 

  12. Saravanamurugan, S.; Palanichamy, M.; Arabindoo, B.; Murugesan, V. J. Mol. Catal. A: Chem. 2004, 218, 101.

    Article  CAS  Google Scholar 

  13. (a) Kloestra, K. R.; Bekkum, H. V. J. Chem. Soc. Chem. Commun. 1995, 1005. (b) Muthukrishnan, M.; Mujahid, M.; Punitharasu, V.; Dnyaneshwar, D. A. Synth. Commun. 2010, 40, 1391.

  14. Kumar, D.; Patel, G.; Mishra, B. G.; Varma, R. S. Tetrahedron Lett. 2007, 49, 6974.

    Article  Google Scholar 

  15. Kumar, D.; Patel, G.; Kumar, A.; Roy, R. K. J. Heterocycl. Chem. 2009, 46, 791.

    Article  CAS  Google Scholar 

  16. Dittmer, C.; Raabe, G.; Hintermann, L. Eur. J. Org. Chem. 2007, 5886.

  17. (a) Varma, R. S.; Saini, R. K. Synlett 1997, 857. (b) Kumar, K. H.; Perumal, P. T. Can. J. Chem. 2006, 84, 1079. (c) Tokes, A. L.; Litkei, G. Synth. Commun. 1993, 23, 895.

  18. Kumar, K. H.; Muralidharan, D.; Perumal, P. T. Synthesis 2004, 63.

  19. Ahmed, N.; Van Lier, J. E. Tetrahedron Lett. 2007, 48, 13.

    Article  CAS  Google Scholar 

  20. Ahmed, N.; Van Lier, J. E. Tetrahedron Lett. 2006, 47, 2725.

    Article  CAS  Google Scholar 

  21. (a) Simons, M.; Teague, R. M. J. Org. Chem. 1970, 35, 2286. (b) Tanaka, K.; Sugino, T. Green Chem. 2001, 3 133.

  22. (a) Harris, T. M.; Carney, R. L. J. Am. Chem. Soc. 1967, 89, 6734. (b) Hoshino, Y.; Takeno, N. Bull. Chem. Soc. Jpn. 1986, 59, 2903.

  23. Sanicanin, Z.; Tabakovic, I. Tetrahedron Lett. 1986, 27, 407.

    Article  CAS  Google Scholar 

  24. Stermitz, F. R.; Adamovics, J. A.; Geigert, J. Tetrahedron 1975, 31, 1593.

    Article  CAS  Google Scholar 

  25. Ali, S. M.; Iqbal, J.; Ilyas, M. J. Chem. Res., Synop. 1984, 236.

  26. Saravanamurugan, S.; Palanichamy, M.; Arabindoo, B.; Murugesan, V. Catal. Commun. 2005, 6, 399.

    Article  CAS  Google Scholar 

  27. (a) Tokes, A. L.; Szilagyi, L. Synth. Commun. 1987, 17, 1235. (b) Tokes, A. L.; Litkei, G.; Szilagyi, L. Synth. Commun. 1992, 22, 2433.

  28. (a) Varma, R. S.; Saini, R. K. Synlett 1997, 857. (b) Kumar, K. H.; Muralidharan, D.; Perumal, P. T. Synthesis 2004, 63.

  29. (a) Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S. M. S. Tetrahedron 2005, 61, 1015. (b) Song, C. E. Chem. Commun. 2004, 1033. (c) Binnemans, K. Chem. Rev. 2007, 107, 2592. (d) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3773. (e) Earle, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391. (f) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. (g) Welton, T. Chem. Rev. 1999, 99, 2071. (h) Ionic Liquids in Synthesis; Wasserscheid, P.; Welton, T., Eds.; Wiley-VCH: Weinheim, 2002. (i) Zhao, H. Malhotra, S. V. Aldrichim. Acta 2002, 35, 75.

  30. (a) Chippe, C.; Melai, B.; Sanzone, A.; Valentini, G. Pure Appl. Chem. 2009, 81, 2035. (b) Yang, Z.-Z.; He, L.-N.; Dou, X.-Y.; Chanfreau, S. Tetrahedron Lett. 2010, 51, 2931. (c) Xu, D.-Z.; Liu, Y.; Shi, S.; Wang, Y. Tetrahedron: Asymmetry 2010, 21, 2530. (d) Wykes, A.; MacNeil, S. L. Synlett 2007, 107. (e) Dyson, P. J.; Grossel, M. C.; Welton, T. J. Chem. Soc., Dalton Trans. 1997, 3465. (f) Suarez, P. A. Z.; Dupont, J. Polyhedron 1996, 15, 1217. (g) Yang, Z. Z.; He, L. N.; Dou, X. Y.; Chanfreau, S. Tetrahedron Lett. 2010, 51, 2931. (h) Mulik, A.; Chandam, D.; Patil, P.; Patil, D. J. Mol. Liq. 2013, 179, 104. (i) Zare-Bidaki, A.; Davoodnia, A. Bull. Korean Chem. Soc. 2012, 33, 1154.

  31. Pretti, C.; Renzi, M.; Focardi, S. E.; Giovani, A.; Monni, G.; Melai, B.; Rajamani, S.; Chiappe, C. Ecotoxicol. Environ. Saf. 2011, 74, 748.

    Article  CAS  Google Scholar 

  32. (a) Kumar, D.; Patel, G.; Kumar, A; Roy, R. K. J. Heterocycl. Chem. 2009, 46, 791. (b) Rao, V. K.; Rao, M. S.; Kumar, A. J. Heterocycl. Chem. 2011, 48, 1356.

  33. (a) Zheng, X.; Jiang, H.; Xie, J.; Yin, Z.; Zhang, H. Synth. Commun. 2013, 43, 1023. (b) Kanagaraj, K.; Pitchumani, K. J. Org. Chem. 2013, 78, 744. (c) Bhattacharya, R. N.; Kundu, P.; Maiti, G. Synth. Commun. 2010, 40, 476. (d) Chandrasekhar, S.; Chatla, S.; Mukhopadhyay, D.; Ganganna, B.; Vijeender, S.; Srihari, P.; Bhadra, U. Bioorg. Med. Chem. Lett. 2012, 22, 645. (e) Xia, Y.; Yang, Z-Y.; Xia, P.; Bastow, K. F.; Tachibana, Y.; Kuo, S-Ch.; Hamel, E.; Hackl, T.; Lee, K-H. J. Med. Chem. 1998, 41, 1155.

  34. Hasaninejad, A.; Shekouhy, M.; Golzar, N.; Zare, A.; Doroodmand, M. M. Appl. Catal., A 2011, 402, 11.

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratory of Synthesis of Molecules with Biological Interest, University of Constantine 1, Constantine, 25000, Algeria

    Chamseddine Derabli, Sara Mahdjoub, Raouf Boulcina, Boudjemaa Boumoud & Abdelmadjid Debache

  2. Chemistry Research Unit in Environmental and Molecular Structure, University of Constantine 1, Constantine, 25000, Algeria

    Hocine Merazig

Authors
  1. Chamseddine Derabli
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sara Mahdjoub
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Raouf Boulcina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Boudjemaa Boumoud
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hocine Merazig
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Abdelmadjid Debache
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Raouf Boulcina.

Additional information

Supplementary information file to this article containing selected spectral and analytical data of the synthesized compounds is available online at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(2), 99–103

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 2599 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Derabli, C., Mahdjoub, S., Boulcina, R. et al. [C8dabco]Br: a mild and convenient catalyst for intramolecular cyclization of 2-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones. Chem Heterocycl Comp 52, 99–103 (2016). https://doi.org/10.1007/s10593-016-1840-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1840-8

Keywords

Search

Navigation