JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 63 No 4 (2018): Journal of the Chilean Chemical Society
Original Research Papers

SALICYLIC ACID AS AN EFFICIENT CATALYST FOR THE DIASTEREOSELECTIVE SYNTHESIS OF DISPIROHYDROQUINOLINES VIA A ONE-POT DOMINO EIGHT-COMPONENT REACTION

Sajjad Salahi
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan
Nourallah Hazeri
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan
Malek Taher Maghsoodlou
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan
Mojtaba Lashkari
Faculty of Science, Velayat University
Niloufar Akbarzadeh Torbati
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan
Santiago García-Granda
Department of Physical and Analytical Chemistry, University of Oviedo-CINN
Laura Torre-Fernández
Department of Physical and Analytical Chemistry, University of Oviedo-CINN
Published January 9, 2019
Keywords
  • Aromatic aldehydes,
  • Aromatic amines,
  • Meldrum’s acid,
  • Dispiro compounds
How to Cite
Salahi, S., Hazeri, N., Taher Maghsoodlou, M., Lashkari, M., Akbarzadeh Torbati, N., García-Granda, S., & Torre-Fernández, L. (2019). SALICYLIC ACID AS AN EFFICIENT CATALYST FOR THE DIASTEREOSELECTIVE SYNTHESIS OF DISPIROHYDROQUINOLINES VIA A ONE-POT DOMINO EIGHT-COMPONENT REACTION. Journal of the Chilean Chemical Society, 63(4). Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/908

Abstract

Salicylic acid was used as an efficient catalyst for the diastereoselective synthesis of dispirohydroquinoline-bis (Meldrim’s acid) derivatives via a one-pot domino eight-component reaction of arylamines, aromatic aldehydes and Meldrum’s acid in CH3CN at room temperature. The remarkable advantages offered by this method are inexpensive catalyst, good yields, simple and easy work-up procedure. The characterization of products was done by IR, mass, 1H NMR, 13C NMR spectroscopy, and elemental analyses. The stereoselectivity of compounds was confirmed with crystallography and NMR spectroscopy.

References

  1. Dömling, Chem. Rev. 106, 17 (2006).
  2. R.V.A. Orru, M. de Greef, Synthesis 10, 1471 (2003).
  3. Hulme, V. Gore, Curr. Med. Chem. 10, 51 (2003).
  4. Montagne, J.J Shiers, M. Shipman, Tetrahedron Lett. 47, 9207 (2006).
  5. R.W. Carling, P.D. Leeson, A.M. Moseley, R. Baker, A.C. Forster, S. Grimwood, J.A. Kemp, G.R. Marshall, J. Med. Chem. 35, 1942 (1992).
  6. S. X. Cai, Z-L. Zhou, J-C. Huang, E.R. Whittermore, Z.O. Egbuwoku, J.E. Hawkinson, R.M. Woodward, J.F. Keana, J. Med. Chem. 39, 3248 (1996).
  7. I. Jacquemond-Collet, F. Benoit-Vical, A. Valentin, E. Stanislas, M. Mallie, I. Fouraste, Planta Med. 68, 68 (2002).
  8. O.B. Wallace, K.S. Lauwers, S.A. Jones, J.A. Dodge, Bioorg. Med. Chem. Lett. 13, 1907 (2003).
  9. Jacobs, M. Frotscher, G. Dannhardt, R.W. Hartmann, J. Med. Chem. 43, 1841 (2000).
  10. G. Dorey, B. Lockhart, P. Lestage, P. Casara, Bioorg. Med. Chem. Lett. 10, 935 (2000).
  11. T.T. Nishiyama, Y.Y. Hashiguchi, S.T. Sakata, T.T. Sakaguchi, Polym. Degrad. Stab.79, 225 (2003).
  12. W. Calhoun, R.P. Carlson, R. Crossley, L.J. Datko, S. Dietrich, K. Heatherington, L.A. Marshall, P.J. Meade, A. Opalko, R.G. Shepherd, J. Med. Chem. 38, 1473 (1995).
  13. Schmittel, M. Strittmatter, K. Vollmann, S. Kiau, Tetrahedron Lett. 37, 999 (1996).
  14. H.A. Etman, M.A. Sofan, M.A. Metwally, Boll. Chim. Farm. 134, 249 (1995).
  15. Hazeri, M. T. Maghsoodlou, S. M. Habibi-Khorassani, G. Marandi, K. Khandan-Barani, M. Ziyaadini, A. Aminkhani, ARKIVOC i, 173 (2007).
  16. M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Moradi, N. Hazeri, A. Davodi, S. S. Sajadikhah, Tetrahedron 67, 8492 (2011).
  17. M.T. Maghsoodlou, S.M. Habibi-Khorassani, R. Heydari, F. Rostami- Charati, N. Hazeri, M. Lashkari, M. Rostamizadeh, G. Marandi, A. Sobolev, M. Makha, Tetrahedron Lett. 50, 4439 (2009).
  18. N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, M. Ziyaadini, G. Marandi, K. Khandan-Barani, H.R. Bijanzadeh, ARKIVOC xiii, 34 (2007).
  19. Salahi, M. T. Maghsoodlou, N. Hazeri, M. Lashkari, N. Akbarzadeh Torbati, M.A. Kazemian, S. García-Granda, L. Torre-Fernández J. Saudi Chem. Soc. 20, 349 (2016).
  20. Salahi, M. T. Maghsoodlou, N. Hazeri, M. Lashkari, S. Garcia-Granda, L. Torre-Fernandez Chin. J. Catal. 36, 1023 (2015).
  21. M. Lashkari, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, N. Akbarzadeh-Torbati, S. García-Granda, L. Torre-Fernández, J. Heterocyclic Chem., 52, 873 (2015).
  22. S. Salahi, N. Hazeri, M.T. Maghsoodlou, S. García-Granda, L. Torre- Fernández, J. Chem. Res. 38, 383 (2014).
  23. N. Hazeri, M. Lashkari, S. García-Granda, L. Torre-Fernández, Aust. J. Chem. 67, 1656 (2014).
  24. D.B. Ramachary, N.S. Chowdari, C.F. Barbas III, Angew. Chem. Int. Ed. 42, 4233 (2003).
  25. D.B. Ramachary, K. Anebousely, N.S. Chowdari, C.F. Barbas III, J. Org. Chem. 69, 5838 (2004).
  26. D.B. Ramachary, N.S. Chowdari, C.F. Barbas III, Synlett 12, 1910 (2003).
  27. B. Jiang, W.-J. Hao, J.-P. Zhang, S.-J. Tu, F. Shi, Org. Biomol. Chem. 7, 2195 (2009).
  28. E.S. Shults, E.A. Semenov, A.A. Johnson, S.P. Bondarenko, I.Y. Bagryanskaya, Y.V. Gatilov, G.A. Tolstikov, Y. Pommier, Bioorg. Med. Chem. Lett. 17, 1362 (2007).
  29. J. Shi, Y. Liu, M. Wang, L. Lin, X. Liu, X. Feng, Tetrahedron 67, 1781 (2011).
  30. Pizzirani, M. Roberti, M. Recanatini, Tetrahedron Lett. 48, 7120 (2007).
  31. W.-J. Hao, B. Bo Jiang, S.-J. Tu, S.-S. Wu, Z.-G. Han, X.-D. Cao, X.-H. Zhang, S. Yan, F. Shi, J. Comb. Chem. 11, 310 (2009).
  32. D. Pizzirani, M. Roberti, S. Grimaudo, A. Di Cristina, R.M. Pipitone, M. Tolomeo, M. Recanatini, J. Med. Chem. 52, 6936 (2009).
  33. P. Wang, L. Song, H. Yi, M. Zhang, S. Zhu, H. Deng, M. Shao, Tetrahedron Lett. 51, 3975 (2010).
  34. S.-J. Tu, X. Zhu, J. Zhang, J. Xu, Y. Zhang, Q. Wang, R. Jia, B. Jiang, J. Zhang, C. Yao, Bioorg. Med. Chem. Lett. 16, 2925 (2006).
  35. X.-S. Wang, M.-M. Zhang, H. Jiang, C.-S. Yao, S.-J. Tu, Tetrahedron. 21, 4439 (2007).
  36. J. Sun, E.-Y. Xia, Q. Wu, C.-G. Yan, ACS Comb. Sci. 13, 421 (2011).
  37. Agilent (2013). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.
  38. M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, M. Mallamo, A. Mazzone, G. Polidori, R. Spagna, J. Appl. Cryst. 45, 357 ( 2012).
  39. G.M. Sheldrick, Acta Cryst. 64, 112 (2008).
  40. L.J. Farrugia, J. Appl. Cryst. 30, 565 (1997).
  41. L.J. Farrugia, J. Appl. Cryst. 32, 837 (1999).

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP