JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 63 No 1 (2018): Journal of the Chilean Chemical Society
Original Research Papers

PHTHALIC ACID: A GREEN, BIODEGRADABLE AND ENVIRONMENTALLY BENIGN NATURE DIFUNCTIONAL BRØNSTED ACID CATALYST FOR THE ONE-POT SYNTHESIS OF 3, 4-DIHYDROPYRIMIDIN-2- (1H)-ONE DERIVATIVES AND SUBSTITUTED DIHYDRO-2-OXYPYRROLES

Farzaneh Mohamadpour
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan
Mojtaba Lashkari
Faculty of Science, Velayat University, Iranshahr
Malek Taher Maghsoodlou
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan
Reza Heydari
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan
Published April 25, 2018
Keywords
  • Phthalic acid,
  • 3,
  • 4-Dihydropyrimidinone,
  • Substituted dihydro-2-oxypyrrole,
  • Biodegradable green catalyst,
  • Multi-component reactions,
  • Green chemistry
  • ...More
    Less

Abstract

Phthalic acid as a green, biodegradable economical and environmentally benign nature catalyst for the one-pot three-component Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives via β-keto esters, aldehyde derivatives and urea/thiourea under thermal and solvent-free conditions and one-pot four-component domino condensation of substituted dihydro-2-oxypyrrole by reaction of dialkyl acetylenedicarboxylate, formaldehyde and amines (aromatic and aliphatic) under ambient temperature with short reaction times and excellent yields is reported. The most benefits this procedure are such as green, biodegradable, inexpensive and non-toxic catalyst, eco-friendly, high catalytic activity, efficient, easily separation with no column chromatographic separation, simple operational procedures, one-pot, excellent yields, environmentally benign nature.

References

  1. M.D. Nikam, P. Mahajan, A.V. Chate, S. Dabhade, C. Gill, J. Chil. Chem. Soc. 60, 2847, (2015).
  2. M. Nasr-esfahani, M. Montazerohori, M. Aghel-mirrezaee, H.Kashi, J. Chil. Chem. Soc. 2014, 59, 2311, (2014).
  3. P.S. Anikt, N. Jaiprakash, N.B. Sangshetti, A.P. Dharbale, P.S. Sarkate wakte, D.B. Shinde, J. Chil. Chem. Soc. 2013, 58, 2200, (2013).
  4. Z. Madanifar, M.T. Maghsoodlou, M. Kangani, N. Hazeri, Res. Chem. Intermed. DOI: 10.1007/s11164-015-1993-6 (2015).
  5. P. Biginelli Gazz Chim Ital. 23, 360, (1893).
  6. S. Wisen, J. Androsavich, C.G. Evans, L. Chang, J.E. Gestwicki , Bioorg. Med. Chem. Lett.18, 60, (2008).
  7. O. Prakash, R. Kumar, V. Parkash, Eur. J. Med. Chem. 43, 435, (2008).
  8. A.D. Borthwick, A.J. Crame, P.F. Ertl, A.M. Exall, T.M. Haley, G.J. Hart, A.M. Mason, M.K. Pennell, O.M.P. Singh, G.G. Weingarten, J.M. Weingarten, J. Med. Chem. 45, 1, (2002).
  9. R. Shiraki, A. Sumino, K. Tadano, S. Ogawa, Tetrahedron Lett. 36, 5551, (1995).
  10. Y. Chen, D.X. Zeng, N. Xie, Y.Z. Dang, J. Org. Chem. 70, 5001, (2005).
  11. B.B. Snider, B.J. Neubert, J. Org. Chem. 69, 8952, (2004).
  12. I.A. Khodja, R. Boulcina, A. Debache, J. Chem. Pharm. Res. 6,1040, (2014).
  13. Y. Zhang, B. Wang, X. Zhang, J. Huang, C. Liu, Molecules. 20, 3811, (2015).
  14. S.B. Singh, M.A. Goetz, E.T. Jones, G.F. Billes, R.A. Giacobbe, L. Herranz, S. Stevens Miles, D.L. Williams, J. Org. Chem. 60, 7040, (1995).
  15. S. Chitra, K. Pandiarajan, TetrahdronLett. 50, 2222, (2009).
  16. A. Kamal, T. Krishnaji, M.A. Azhar, J.Catal. Commun. 8, 1929, (2007).
  17. J. Lai, M. Sharma, S. Gupta, P. Parashar, P. Sahu, D.D. Agarwal, J. Mol. Catal. A. Chem. 352, 31, (2012).
  18. A. Kumar, R.A. Maurya, Tetrahedron Lett. 48, 4569, (2007).
  19. M. Litvic, I. Vecenaj, Z.M. Ladisic, M. Lovric, V. Vinkovic, M. Filipan- Litvic,Tetrahedron. 66, 3463, (2010).
  20. C.J. Liu, J.D. Wang, Molecules. 14, 763, (2009).
  21. A.T. Khan, A. Ghosh, M. Musawwer Khan, Tetrahedron Lett. 53, 2622, (2012).
  22. Q. Zhu, H. Jiang, J. Li, S. Liu, C. Xia, M. Zhang, J. Comb. Chem. 11, 685, (2009).
  23. S. S. Sajadikhah, N. Hazeri, J. Res. Chem. Intermed. 40, 737, (2014).
  24. S.S. Sajadikhah, N. Hazeri, M.T, Maghsoodlou, S.M. Habibi Khorasani, A. Beigbabaei, A. C. Willis., J. Iran. Chem. Soc. 10, 863, (2013).
  25. S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, J. Chem. Res. 37, 40, (2013).
  26. S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S. Mohamadian-Souri, Res. Chem. Intermed. DOI: 10.1007/s11164-015-2178-z (2015).
  27. S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, Chin. Chem. Lett. 25, 58, (2014).
  28. S. Sajjadifar, M.A. Zolfi gol, A. Ghorbani-Choghamarani, A.R. Banaei, S. Karimian, S. Miri Scientia. Iranica. 21, 2005, (2014).
  29. S. Sajjadifar, S. Miri, Int. J. Chem. Tech. Res. CODEN (USA): IJCRGG. 6, 5433 (2014).
  30. F.M. Danikuu, E.N.K. Sowley, J. Med & Biomed. Sci. 3, 9, (2014).

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