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Research on Chemical Intermediates

, Volume 43, Issue 11, pp 6233–6243 | Cite as

Microwave-irradiated one-pot synthesis of quinoline derivatives catalyzed by triethylamine

  • Sanele Moloi
  • Suresh Maddila
  • Sreekantha B. JonnalagaddaEmail author
Article

Abstract

An efficient and swift microwave (MW)-mediated procedure for synthesis of 11 quinoline derivatives has been designed based on reaction between aromatic aldehydes, malononitrile, 5,5-dimethylcyclohexane-1,3-dione, and ammonium acetate at room temperature in ethanol solvent. The main advantages of this method are operational simplicity, excellent yield (92–98 %), use of green solvent, short reaction time (<15 min), mild reaction condition, and no byproducts.

Graphical Abstract

Keywords

Green chemistry Quinoline One-pot synthesis Microwave Multicomponent reaction 

Notes

Acknowledgements

The authors are grateful to the National Research Foundation (NRF) of South Africa, and University of KwaZulu-Natal, Durban, for financial support and research facilities.

Supplementary material

11164_2017_2986_MOESM1_ESM.doc (2.7 mb)
Supplementary material 1 (DOC 2783 kb)

References

  1. 1.
    R.A. Sheldon, Green Chem. 9, 1273 (2007)CrossRefGoogle Scholar
  2. 2.
    I.T. Horvath, P.T. Anastas, Chem. Rev. 107, 2167 (2007)CrossRefGoogle Scholar
  3. 3.
    T. Collins, Science 291, 48 (2001)CrossRefGoogle Scholar
  4. 4.
    S. Shabalala, S. Maddila, W.E. Van Zyl, S.B. Jonnalagadda, Catal. Commun. 79, 21 (2016)CrossRefGoogle Scholar
  5. 5.
    N. Shabalala, S. Maddila, S.B. Jonnalagadda, New J. Chem. 40, 5107 (2016)CrossRefGoogle Scholar
  6. 6.
    S. Maddila, S. Rana, R. Pagadala, S. Kankala, S.N. Maddila, S.B. Jonnalagadda, Catal. Commun. 61, 26 (2015)CrossRefGoogle Scholar
  7. 7.
    N. Shabalala, S. Maddila, S.B. Jonnalagadda, Res. Chem. Intermed. 42, 8097 (2016)CrossRefGoogle Scholar
  8. 8.
    S. Maddila, K.K. Gangu, S.N. Maddila, S.B. Jonnalagadda, Mol. Divers. 21, 247 (2017)CrossRefGoogle Scholar
  9. 9.
    S.N. Maddila, S. Maddila, W.E. Van Zyl, S.B. Jonnalagadda, Res. Chem. Intermed. 42, 2553 (2016)CrossRefGoogle Scholar
  10. 10.
    S.N. Maddila, S. Maddila, W.E. Van Zyl, S.B. Jonnalagadda, Curr. Org. Chem. 20, 2125 (2016)CrossRefGoogle Scholar
  11. 11.
    J. Bo, S. Feng, T. Shu-Jiang, Curr. Org. Chem. 14, 357 (2010)CrossRefGoogle Scholar
  12. 12.
    E.S.H. El Ashry, E. Ramadan, A.A. Kassem, M. Hagar, Adv. Heterocyc. Chem. 88, 1 (2005)CrossRefGoogle Scholar
  13. 13.
    Y. Gu, Green Chem. 14, 2091 (2012)CrossRefGoogle Scholar
  14. 14.
    D.H. Antonio, A. Loupy (eds.), Microwaves in Organic Synthesis, vol. 2 (Wiley, New York, 2013)Google Scholar
  15. 15.
    I.J. Cutress, F. Marken, R.G. Compton, Electroanalysis 21, 113 (2009)CrossRefGoogle Scholar
  16. 16.
    P. Lidstrom, J. Tierney, B. Wathey, J. Westman, Tetrahedron 57, 9225 (2001)CrossRefGoogle Scholar
  17. 17.
    S. Gorle, S. Maddila, S.N. Maddila, K. Naicker, M. Singh, P. Singh, S.B. Jonnalagadda, Anti Cancer Agents Med. Chem. 17, 464 (2017)CrossRefGoogle Scholar
  18. 18.
    S. Maddila, R. Pagadala, S.B. Jonnalagadda, Lett. Org. Chem. 10, 693 (2013)CrossRefGoogle Scholar
  19. 19.
    V. Polshettiwar, R.S. Varma, Chem. Soc. Rev. 37, 1546 (2008)CrossRefGoogle Scholar
  20. 20.
    S. Maddila, S.B. Jonnalagadda, Lett. Org. Chem. 10, 374 (2013)CrossRefGoogle Scholar
  21. 21.
    S. Gorle, S. Maddila, S. Chokkakula, P. Lavanya, M. Singh, S.B. Jonnalagadda, J. Heterocyc. Chem. 53, 1852 (2016)CrossRefGoogle Scholar
  22. 22.
    K. Suresh, B. Sandhya, G. Himanshu, Mini. Rev. Med. Chem. 9, 1648 (2009)CrossRefGoogle Scholar
  23. 23.
    D. Verbanac, R. Malik, M. Chand, K. Kushwaha, M. Vashist, M. Matijasic, V. Stepanic, M. Peric, H.C. Paljetak, L. Saso, S.C. Jain, J. Enzyme Inhib. Med. Chem. 19, 1 (2016)Google Scholar
  24. 24.
    S. Cretton, S. Dorsaz, A. Azzollini, Q. Favre-Godal, L. Marcourt, S.N. Ebrahimi, F. Voinesco, E. Michellod, D. Sanglard, K. Gindro, J.L. Wolfender, M. Cuendet, P. Christen, J. Nat. Prod. 79, 300 (2016)CrossRefGoogle Scholar
  25. 25.
    M.M. Ghorab, M.S. Alsaid, M.S. Al-Dosari, F.A. Ragab, A.A. Al-Mishari, A.N. Almoqbil, Acta Pharm. 66, 155 (2016)CrossRefGoogle Scholar
  26. 26.
    X.Q. Deng, M.X. Song, Y. Zheng, Z.S. Quan, Eur. J. Med. Chem. 73, 217 (2014)CrossRefGoogle Scholar
  27. 27.
    I. Briguglio, R. Loddo, E. Laurini, M. Fermeglia, S. Piras, P. Corona, P. Giunchedi, E. Gavini, G. Sanna, G. Giliberti, C. Ibba, P. Farci, P. La Colla, S. Pricl, A. Carta, Eur. J. Med. Chem. 105, 63 (2015)CrossRefGoogle Scholar
  28. 28.
    R. de Meneses Santos, P.R. Barros, J.H. Bortoluzzi, M.R. Meneghetti, Y.K. da Silva, A.E. da Silva, M.S. da Silva, M.S. Alexandre-Moreira, Bioorg. Med. Chem. 23, 4390 (2015)CrossRefGoogle Scholar
  29. 29.
    D.W. Wang, H.Y. Lin, R.J. Cao, T. Chen, F.X. Wu, G.F. Hao, Q. Chen, W.C. Yang, G.F. Yang, J. Agric. Food Chem. 63, 5587 (2015)CrossRefGoogle Scholar
  30. 30.
    M.R. Aly, M.M. Ibrahim, A.M. Okael, Y.A. Gherbawy, Bioorg. Khim. 40, 234 (2014)Google Scholar
  31. 31.
    A. Amoozadeh, S. Rahmani, M. Bitaraf, F.B. Abadi, E. Tabrizian, New J. Chem. 40, 770 (2016)CrossRefGoogle Scholar
  32. 32.
    M. Abaszadeh, M. Seifi, A. Asadipour, Res. Chem. Intermed. (2014). doi: 10.1007/s11164-014-1624-7 Google Scholar
  33. 33.
    B. Amirheidari, M. Seifi, M. Abaszadeh, Res. Chem. Intermed. (2015). doi: 10.1007/s11164-015-2220-1 Google Scholar
  34. 34.
    M. Suarez, Y. Verdecia, E. Ochoa, N. Martin, R. Martinez, M. Quinteiro, C. Seoane, J.L. Soto, H. Novoa, N. Blaton, O.M. Peeters, C. De Ranter, J. Heterocyc. Chem. 37, 735 (2000)CrossRefGoogle Scholar
  35. 35.
    A. Siddekha, S.H.S. Azzam, M.A. Pasha, Syn. Commun. 44, 424 (2014)CrossRefGoogle Scholar
  36. 36.
    S. Maddila, S.B. Jonnalagadda, J. Chil. Chem. Soc. 57, 1099 (2012)CrossRefGoogle Scholar
  37. 37.
    S. Maddila, S. Rana, R. Pagadala, S.B. Jonnalagadda, Res. Chem. Intermed. 41, 8269 (2015)CrossRefGoogle Scholar
  38. 38.
    S. Maddila, S.N. Maddila, S.B. Jonnalagadda, P. Lavanya, J. Heterocyc. Chem. 53, 658 (2016)CrossRefGoogle Scholar
  39. 39.
    S. Maddila, K. Naicker, S. Gorle, S. Rana, Y. Kotaiah, S.N. Maddila, M. Singh, P. Singh, S.B. Jonnalagadda, Anti Cancer Agents Med. Chem. 16, 1031 (2016)CrossRefGoogle Scholar
  40. 40.
    S. Maddila, K. Naicker, M. Momin, S. Rana, S. Gorle, S.N. Maddila, Y. Kotaiah, M.I. Singh, S.B. Jonnalagadda, Med. Chem. Res. 25, 283 (2016)CrossRefGoogle Scholar
  41. 41.
    S. Maddila, M. Momin, S. Gorle, P. Lavanya, S.B. Jonnalagadda, J. Chil. Chem. Soc. 60, 2774 (2015)CrossRefGoogle Scholar
  42. 42.
    S. Maddila, S. Gorle, N. Seshadri, P. Lavanya, S.B. Jonnalagadda, Arab. J. Chem. 9, 681 (2016)CrossRefGoogle Scholar
  43. 43.
    S. Maddila, S. Gorle, M. Singh, P. Lavanya, S.B. Jonnalagadda, Lett. Drug Des. Discov. 10, 977 (2013)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2017

Authors and Affiliations

  1. 1.School of Chemistry and PhysicsUniversity of KwaZulu-NatalDurbanSouth Africa

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