Skip to main content
SpringerLink
Log in

Facile one-pot synthesis of a novel series of 7-aryl-8H-benzo[h]indeno[1,2-b]quinoline-8-one derivatives catalyzed by tribromomelamine

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Tribromomelamine, has been used as an efficient, inexpensive, and green catalyst for one-pot, three-component synthesis of 7-aryl-8H-benzo[h]indeno[1,2-b]quinoline-8-ones by reaction of 1,3-indanedione, aromatic aldehydes, and 1-naphthylamine under solvent-free conditions. The several advantages of this reaction include high yields, short reaction time, and high catalyst efficiency.

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

Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. B. Adrom, N. Hazeri, M.T. Maghsoodlou, M. Mollamohammadi, Res. Chem. Intermed. (2014). doi:10.1007/s11164-014-1564-2

    Google Scholar 

  2. H. Kiyani, F. Ghorbani, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1508-2

    Google Scholar 

  3. K.A. Werbovetz, A.K. Bhattacharjee, J.J. Brendle, J.P. Scovill, Bioorg. Med. Chem. 8, 1741 (2000)

    Article  CAS  Google Scholar 

  4. C.H. Tseng, R.W. Lin, Y.L. Chen, G.J. Wang, M.L. Ho, C.C. Tzeng, J. Med. Chem. 54, 3103 (2011)

    Article  CAS  Google Scholar 

  5. Y.W. Chen, Y.L. Chen, C.H. Tseng, C.C. Liang, C.N. Yang, Y.C. Yao, P.J. Lu, C.C. Tzeng, J. Med. Chem. 54, 4446 (2011)

    Article  CAS  Google Scholar 

  6. C.H. Tseng, Y.L. Chen, K.Y. Chung, C.H. Wang, S.I. Peng, C.M. Cheng, C.C. Tzeng, Org. Biomol. Chem. 9, 3205 (2011)

    Article  CAS  Google Scholar 

  7. C.L. Yang, C.H. Tseng, Y.L. Chen, C.M. Lu, C.L. Kao, M.H. Wu, C.C. Tzeng, Eur. J. Med. Chem. 45, 602 (2010)

    Article  CAS  Google Scholar 

  8. S. Chakrabarty, M.S. Croft, M.G. Marko, G. Moyna, Bioorg. Med. Chem. 21, 1143 (2013)

    Article  CAS  Google Scholar 

  9. R.S. Upadhayaya, V. Jaya, Kishore, V. Nageswara Rao, V. Sharma, S. S. Dixit. J. Chattopadhyaya Bioorg. Med. Chem. 17, 2830 (2009)

    Article  CAS  Google Scholar 

  10. R.S. Upadhayaya, G.M. Kulkarni, V. Jaya Kishore, V. Nageswara Rao, V. Sharmat, S.S. Dixit, J. Chattopadhyaya, Bioorg. Med. Chem. 17, 4681 (2009)

    Article  CAS  Google Scholar 

  11. R.S. Upadhayaya, V. Jaya Kishore, R.A. Kardile, S.V. Lahore, S.S. Dixit, H.S. Deokar, P.D. Shinde, J. Chattopadhyaya, Eur. J. Med. Chem. 45, 1854 (2010)

    Article  CAS  Google Scholar 

  12. R.S. Upadhayaya, S.V. Lahore, A.Y. Sayyed, S.S. Dixit, P.D. Shinde, J. Chattopadhyaya, Org. Biomol. Chem. 8, 2180 (2010)

    Article  CAS  Google Scholar 

  13. R.S. Upadhayaya, P.D. Shinde, A.Y. Sayyed, S.A. Kadam, A.N. Bawane, A. Poddar, O. Plashkevych, A. Földesi, J. Chattopadhyaya, Org. Biomol. Chem. 8, 5661 (2010)

    Article  CAS  Google Scholar 

  14. R.S. Upadhayaya, P.D. Shinde, S.A. Kadam, A.N. Bawane, A.Y. Sayyed, R.A. Kardile, P.N. Gitay, S.V. Lahore, S.S. Dixit, A. Földesi, J. Chattopadhyaya, Euro. J. Med. Chem. 46, 1306 (2011)

    Article  CAS  Google Scholar 

  15. C.H. Tseng, Y.L. Chen, P.J. Lu, C.N. Yangd, C.C. Tzeng, Bioorg. Med. Chem. 16, 3153 (2008)

    Article  CAS  Google Scholar 

  16. Y.L. Chen, H.M. Hung, C.M. Lu, K.C. Li, C.C. Tzeng, Bioorg. Med. Chem. 12, 6539 (2004)

    Article  CAS  Google Scholar 

  17. M. Mamaghani, T.H. Larghani, J. Chem. Res. 36, 235 (2012)

    Article  CAS  Google Scholar 

  18. X.S. Wang, M.M. Zhang, Z.S. Zeng, D.Q. Shi, S.J. Tu, X.Y. Wei, Z.M. Zong, J. Heterocycl. Chem. 43, 989 (2006)

    Article  CAS  Google Scholar 

  19. S.J. Tu, B. Jiang, R.H. Jia, J.Y. Zhang, Y. Zhang, C.S. Yao, F. Shi, J. Org. Biomol. Chem. 4, 3664 (2006)

    Article  CAS  Google Scholar 

  20. S.J. Tu, S.S. Wu, S. Yan, W.J. Hao, X.H. Zhang, X.D. Cao, Z.G. Han, B. Jiang, F. Shi, M. Xia, J.F. Zhou, J. Comb. Chem. 11, 239 (2009)

    Article  CAS  Google Scholar 

  21. M.M. Heravi, T. Hosseini, F. Derikvand, S.Y.S. Beheshtiha, F.F. Bamoharram, Synth. Commun. 40, 2402 (2010)

    Article  CAS  Google Scholar 

  22. S. Damavandi, R. Sandaroos, Heterocycl. Commun. 17, 121 (2011)

    CAS  Google Scholar 

  23. R. Ssndaroos, M. Vadi, S. Damavandi, J. Chem. Sci. 125, 1497 (2013)

    Article  Google Scholar 

  24. H. Eshghi, M.A. Nasseri, R. Sandaroos, H.R. Molaei, S. Damavandi, Synth. React. Inorg. Metal Org. Nano Metal. Chem. 42, 573 (2012)

    Article  CAS  Google Scholar 

  25. F. Shirini, S.S. Beigbaghlou, S.V. Atghia, S.A.R. Mousazadeh, Dyes Pigm. 97, 19 (2013)

    Article  CAS  Google Scholar 

  26. N.G. Khaligh, Chin. J. Catal. 35, 474 (2014)

    Article  CAS  Google Scholar 

  27. N. G. Khaligh, Res. Chem. Intermed. doi:10.1007/s11164-014-1642-5

  28. A. Ghorbani-Choghamarani, M.A. Zolfigol, M. Hajjami, S. Jafari, J. Chin. Chem. Soc. 55, 1208 (2008)

    Article  CAS  Google Scholar 

  29. L. Wu, E.-J. Nelson, Chem. 9, 1035 (2012)

    CAS  Google Scholar 

  30. A. Ghorbani-Choghamarani, S. Rashidimoghadam, Chin. J. Catal. 35, 1024 (2014)

    Article  CAS  Google Scholar 

  31. M. Hajjami, A. Ghorbani-Choghamarani, Z. Karamshahi, M. Norouzi, Chin. J. Catal. 35, 260 (2014)

    Article  CAS  Google Scholar 

  32. S.S. Mansoor, K. Aswin, K. Logaiya, P.N. Sudhan, S. Malik, Res. Chem. Intermed. 40, 357 (2014)

    Article  CAS  Google Scholar 

  33. M. Ghashang, S.S. Mansoor, K. Aswin, S.P.N. Sudhan, Res. Chem. Intermed. (2014). doi:10.1007/s11164-014-1625-6

    Google Scholar 

  34. S.S. Mansoor, K. Aswin, K. Logaiya, P.N. Sudhan, S. Malik, Res. Chem. Intermed. 40, 871 (2014)

    Article  CAS  Google Scholar 

  35. M. Ghashang, S.S. Mansoor, K. Aswin, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1419-2

    Google Scholar 

Download references

Acknowledgments

The author Mansoor is grateful to C. Abdul Hakeem College Management for facilities and support.

Author information

Authors and Affiliations

  1. Bioactive Organic Molecule Synthetic Unit, Research Department of Chemistry, C. Abdul Hakeem College, Melvisharam, 632 509, Tamil Nadu, India

    Syed Sheik Mansoor & Krishnamoorthy Aswin

  2. Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran

    Majid Ghashang

Authors
  1. Syed Sheik Mansoor
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Majid Ghashang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Krishnamoorthy Aswin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Syed Sheik Mansoor.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mansoor, S.S., Ghashang, M. & Aswin, K. Facile one-pot synthesis of a novel series of 7-aryl-8H-benzo[h]indeno[1,2-b]quinoline-8-one derivatives catalyzed by tribromomelamine. Res Chem Intermed 41, 6907–6926 (2015). https://doi.org/10.1007/s11164-014-1787-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-014-1787-2

Keywords

Search

Navigation