Skip to main content
SpringerLink
Log in

Microwave assisted synthesis of ring junction heterocyclic antioxidants

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

Abstract

A series of 6,7-dihydro-[1,2,4]triazolo[5,1-b]quinazolin-8(5H)-ones, 4a–o were synthesized via a one-pot, multicomponent reaction in the presence of water as a solvent under microwave irradiation using ceric ammonium nitrate as an oxidizing agent. This techno-chemical method provides a rapid construction of higher molecules in short duration with high yield. The adopted method was carried out in the presence of water without catalyst and yielded the compounds without any side products, and thus further purification of compounds by column chromatography was not required. All the synthesized compounds, 4a–o were screened for their 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity. All the compounds, 4a–o possessed moderate antioxidant activity when compared to their standard antioxidant (ascorbic acid).

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

Fig. 1
Fig. 2
Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. K. Hemalatha, G. Madhumitha, A. Kajbafvala, N. Anupama, R. Sompalle, S.M. Roopan, J. Nanomater. 2013(341015), 1 (2013)

    Article  Google Scholar 

  2. D.S. Bose, L. Fatima, H.B. Mereyala, J. Org. Chem. 68, 587 (2003)

    Article  CAS  Google Scholar 

  3. K. Hemalatha, G. Madhumitha, C.S. Vasavi, P. Munusami, J. Photoch. Photobiol. B. 143, 139 (2015)

    Article  CAS  Google Scholar 

  4. T.E. Nielsen, S.L. Screiber, Angew. Chem. Int. Ed. 47, 48 (2008)

    Article  CAS  Google Scholar 

  5. J. Palaniraja, S.M. Roopan, RSC Adv. 5, 37415 (2015)

    Article  CAS  Google Scholar 

  6. S. Makarem, A.A. Mohammadi, A.R. Fakhar, Tetrahedron Lett. 49, 7194 (2008)

    Article  CAS  Google Scholar 

  7. H. Hugel, Molecules 14, 4936 (2009)

    Article  CAS  Google Scholar 

  8. D. Bonne, Y. Coquerel, T. Constantieux, J. Rodriguez, Tetrahedron 21, 1085 (2010)

    Article  CAS  Google Scholar 

  9. A. Bharathi, S.M. Roopan, A. Kajbafvala, R.D. Padmaja, M.S. Darsana, G.N. Kumari, Chin. Chem. Lett. 25, 324–326 (2014)

    Article  CAS  Google Scholar 

  10. J. Palaniraja, S.M. Roopan, RSC Adv. 5, 8640 (2015)

    Article  CAS  Google Scholar 

  11. C. Hulme, V. Gore, Curr. Med. Chem. 10, 51 (2003)

    Article  CAS  Google Scholar 

  12. S.M. Roopan, A. Bharathi, J. Palaniraja, K. Anand, R.M. Gengan, RSC Adv. 5, 38640 (2015)

    Article  CAS  Google Scholar 

  13. S.M. Roopan, F.N. Khan, B.K. Mandal, Tetrahedron Lett. 51, 2309 (2010)

    Article  CAS  Google Scholar 

  14. A. Bharathi, S.M. Roopan, A.A. Rahuman, G. Rajkumar, Res. Chem. Intermed. 41, 2453 (2015)

    Article  CAS  Google Scholar 

  15. M.S. Mohamed, M.M. Kamel, E.M.M. Kassem, N. Abotaleb, S.M. Nofal, M.F. Ahmed, Acta Polon. Pharm Drug Res. 66, 487 (2009)

    CAS  Google Scholar 

  16. P. Ilangovan, S. Ganguly, J. Pharm. Res. 3, 703 (2010)

    CAS  Google Scholar 

  17. S.M. Roopan, F.N. Khan, Chem. Pap. 5, 678 (2010)

    Google Scholar 

  18. M. Chaudhary, S. Bhattacharya, Y. Ahmad, Der Pharm. Lett. 4, 954 (2012)

    CAS  Google Scholar 

  19. X. Gao, X. Cai, K. Yan, B. Song, L. Gao, Z. Chen, Molecules 12, 2621 (2007)

    Article  CAS  Google Scholar 

  20. S.M. Mosaad, K.I. Mohammed, M.A. Ahmed, H.S.G. Abdel, Appl. Sci. 4, 302 (2004)

    Article  Google Scholar 

  21. T. Chandra, N. Garg, A. Kumar, World J. Chem. 4, 210 (2009)

    CAS  Google Scholar 

  22. V. Zyl, F. Etienne, For. Sci. Int. 121, 142 (2011)

    Google Scholar 

  23. B.V. Shetty, Ind. J. Pharm. 6, 40 (1974)

    Google Scholar 

  24. V. Alagarsamy, A. Thangathiruppathy, S.C. Mandal, S. Rajasekaran, S.V. Kumar, R. Revathi, J. Anburaj, S.A. Kumar, S. Rajesh, Ind. J. Pharm. Sci. 68, 108 (2006)

    Article  CAS  Google Scholar 

  25. S.F. Campbell, M.J. Davey, J.D. Hardstone, B.N. Lewis, M.J.J. Palmer, J. Med. Chem. 30, 57 (1987)

    Article  Google Scholar 

  26. S.M. Roopan, F.N. Khan, J.S. Jin, R.S. Kumar, Res. Chem. Intermed. 37, 919 (2011)

    Article  CAS  Google Scholar 

  27. M. Gund, S.M. Roopan, F.R.N. Khan, J.S. Jin, R. Kumar, A.S. Kumar, Res. Chem. Intermed. 38, 1111 (2012)

    Article  CAS  Google Scholar 

  28. F.H. Havaldar, A.R. Patil, Eur. J. Chem. 5, 347 (2008)

    CAS  Google Scholar 

  29. K. Siddappa, T. Reddy, M. Mallikarjun, C.V. Reddy, Eur. J. Chem. 5, 155 (2008)

    Google Scholar 

  30. S. Rajasekaran, G. Rao, Der Pharm. Lett. 4, 349 (2008)

    Google Scholar 

  31. S.M. Roopan, F.N. Khan, J.S. Jin, Chem. Pap. 65, 345 (2011)

    Article  CAS  Google Scholar 

  32. S.M. Roopan, F.N. Khan, J.S. Jin, Res. Chem. Intermed. 38, 443 (2012)

    Article  CAS  Google Scholar 

  33. B.D. Mistry, K.R. Desai, J.A. Patil, Eur. J. Chem. 3, 97 (2006)

    Google Scholar 

  34. P.J. Kothari, M.A. Mehlhoff, S.P. Singh, S.S. Parmar, V.I.J. Stenberg, J. Heterocycl. Chem. 17, 1369 (1980)

    Article  CAS  Google Scholar 

  35. S. Ueda, H.J. Nagasawa, Am. Chem. Soc. 131, 15080 (2009)

    Article  CAS  Google Scholar 

  36. G.P. Ravinder, K. Shuklachary, B. Rajashaker, K. Nagaiah, B.K. Sudhakar, N. Lingaiah, Tetrahedron Lett. 54, 2480 (2013)

    Article  Google Scholar 

  37. M.N. Nasr, M.M. Gineinah, E.R. El-Bendary, Arch. Pharm. 12, 560 (2003)

    Article  Google Scholar 

  38. K. Spirkova, S. Stankovsky, M. Zahradník, Chem. Pap. 51, 403 (1997)

    CAS  Google Scholar 

  39. M.N. Alam, N.J. Bristi, M. Rafiquzzaman, Sudai Pharm. J. 21, 143 (2013)

    Article  Google Scholar 

  40. S. Mandal, S. Yadav, S. Yadav, R.K. Nema, J. Chem. Pharm. Res. 1, 102 (2009)

    Google Scholar 

  41. A.V. Badrinath, K.M. Rao, C.M.S. Chetty, S. Ramakanth, T.V.S. Rajan, K. Gnanaprakash, Int. J. Pharmtech. Res. 2, 1276 (2010)

    Google Scholar 

  42. M.M. Heravi, L. Ranjbar, F. Derikvand, B. Alimadadi, H.A. Oskooie, F.F. Bamoharram, Mol. Divers. 12, 181 (2008)

    Article  CAS  Google Scholar 

  43. P.K. Sahu, P.K. Sahu, S.K. Gupta, D.D. Agarwal, Ind. Eng. Chem. Res. 53, 2085 (2014)

    Article  CAS  Google Scholar 

  44. R.G. Puligoundla, S. Karnakanti, R. Bantu, N. Kommu, S.B. Kondra, L. Nagarapu, Tetrahedron Lett. 54, 2480 (2013)

    Article  CAS  Google Scholar 

  45. M.M. Heravi, F. Derikvand, L. Ranjbar, Synth. Commun. 40, 677 (2010)

    Article  CAS  Google Scholar 

  46. A.F.E. Mourad, A.A. Aly, H.H. Farag, E.A. Beshr, Bilstein J. Org. Chem. 3, 11 (2007)

    Article  Google Scholar 

  47. K.A. Shaikh, S.R. Kande, C.B. Khillare, IOSR J. Applied Chem. 7, 54 (2014)

    Article  Google Scholar 

  48. G. Krishnamurthy, K.V. Jagannath, J. Chem. Sci. 125, 807 (2013)

    Article  CAS  Google Scholar 

  49. K. Kumari, D.S. Raghuvanshi, K.N. Singh, Org. Prep. Proced. Int. 44, 460 (2012)

    Article  CAS  Google Scholar 

  50. M. Kidwai, R. Chauhan, J. Mol. Catal. A Chem. 377, 1 (2013)

    Article  CAS  Google Scholar 

  51. A. Danida, R. Singh, A.K. Jain, D. Singh, Synth. Commun. 38, 3543 (2008)

    Article  Google Scholar 

  52. M.S. Singh, S. Chowdhury, RSC Adv. 2, 4547 (2012)

    Article  CAS  Google Scholar 

  53. S.M. Roopan, F.N. Khan, Ind. J. Heterocycl. Chem. 18, 183 (2008)

    CAS  Google Scholar 

  54. B. Xu, Y. Yu, P. Wan, C. Wan, S. Cao, Res. Chem. Intermed. 40, 3095 (2014)

    Article  CAS  Google Scholar 

  55. S.M. Roopan, F.N. Khan, Arkivoc 2009, 161 (2009)

    Google Scholar 

Download references

Acknowledgments

One of the authors, Dr. S. Mohana Roopan, thanks DST-FTYS Fast Track (No. SB/FT/CS-126/2012), Government of India, New Delhi, for providing the research grants. The authors wish to express their gratitude to SIF, VIT University, for NMR support. The other author, Mr. Rajesh Sompalle, wishes to thank the VIT University Management for providing RA fellowship and the infrastructure. Finally, we also thank Dr. G. Madhumitha, Assistant Professor, School of Advanced Sciences, VIT University, for granting access to the microwave instrumentation.

Author information

Authors and Affiliations

  1. Chemistry of Heterocycles and Natural Product Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore, Tamilnadu, 632 014, India

    Rajesh Sompalle & Selvaraj Mohana Roopan

Authors
  1. Rajesh Sompalle
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Selvaraj Mohana Roopan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Selvaraj Mohana Roopan.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 27014 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sompalle, R., Roopan, S.M. Microwave assisted synthesis of ring junction heterocyclic antioxidants. Res Chem Intermed 42, 5353–5366 (2016). https://doi.org/10.1007/s11164-015-2371-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2371-0

Keywords

Search

Navigation