Advertisement

Imin-based synthesis of polyfunctionalized dihydro-2-oxypyrroles catalyzed by glycine amino acid via tandem Michael–Mannich cyclocondensation reaction under ambient temperature

  • Farzaneh MohamadpourEmail author
Article
  • 15 Downloads

Abstract

An efficient and mild synthetic route to the convenient one-pot preparation of polyfunctionalized dihydro-2-oxypyrroles has been developed and catalyzed via glycine amino acid as a natural bio-based and biodegradable catalyst using imin-based four condensation domino reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde via tandem Michael–Mannich cyclocondensation reaction under ambient temperature. The reactions complete in less time, but the products are obtained in outstanding yields. This environmentally friendly method includes the noticeable properties such as bio-based and green catalyst, direct workup without column chromatographic separation, cost-effective, mild and simple synthesis, one-pot procedure and high atom economy.

Keywords

Polyfunctionalized dihydro-2-oxypyrroles Glycine amino acid Naturally bio-based and biodegradable catalyst High atom economy Imin-based synthesis 

Notes

Acknowledgements

We gratefully acknowledge financial support from the Research council of the Apadana Institute of Higher Education.

Supplementary material

11164_2019_4072_MOESM1_ESM.pdf (884 kb)
Supplementary material 1 (PDF 885 kb)

References

  1. 1.
    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. Woolven, J. Med. Chem. 45, 1 (2002)CrossRefGoogle Scholar
  2. 2.
    C. Alp, D. Ekinci, M.S. Gultekin, M. Senturk, E. Sahin, O. Kufrevioglu, Bioorg. Med. Chem. 18, 4468 (2010)CrossRefGoogle Scholar
  3. 3.
    R. Shiraki, A. Sumino, K. Tadano, S. Ogawa, Tetrahedron Lett. 36, 5551 (1995)CrossRefGoogle Scholar
  4. 4.
    Y.L. Lampe, R.G. Chou, R.G. Hanna, S.V. DiMeo, P.W. Erhardt, A.A. Hagedorn, W.R. Ingebretsen, E. Cantor, J. Med. Chem. 36, 10410 (1993)CrossRefGoogle Scholar
  5. 5.
    Y. Chen, D.X. Zeng, N. Xie, Y.Z. Dang, J. Org. Chem. 70, 5001 (2005)CrossRefGoogle Scholar
  6. 6.
    S.B. Singh, M.A. Goetz, E.T. Jones, G.F. Billes, R.A. Giacobbe, L. Herranz, J. Org. Chem. 60, 7040 (1995)CrossRefGoogle Scholar
  7. 7.
    A.T. Khan, A. Ghosh, M. Musawwer Khan, Tetrahedron Lett. 53, 2622 (2012)CrossRefGoogle Scholar
  8. 8.
    S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, Chin. Chem. Lett. 25, 58 (2014)CrossRefGoogle Scholar
  9. 9.
    S.S. Sajadikhah, N. Hazeri, Res. Chem. Intermed. 40, 737 (2014)CrossRefGoogle Scholar
  10. 10.
    S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, A.C. Willis, J. Iran. Chem. Soc. 10, 863 (2013)CrossRefGoogle Scholar
  11. 11.
    Q. Zhu, H. Jiang, J. Li, S. Liu, C. Xia, M. Zhang, J. Comb. Chem. 11, 685 (2009)CrossRefGoogle Scholar
  12. 12.
    L. Lv, S. Zheng, X. Cai, Z. Chen, Q. Zhu, S. Liu, J. Acs. Comb. Sci. 15, 183 (2013)CrossRefGoogle Scholar
  13. 13.
    S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, J. Chem. Res. 37, 40 (2013)CrossRefGoogle Scholar
  14. 14.
    S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S. Mohamadian-Souri, Res. Chem. Intermed. 42, 2805 (2016)CrossRefGoogle Scholar
  15. 15.
    N. Salehi, B.B.F. Mirjalili, RSC Adv. 7, 30303 (2017)CrossRefGoogle Scholar
  16. 16.
    M. Zarei, S.S. Sajadikhah, Res. Chem. Intermed. 42, 7005 (2016)CrossRefGoogle Scholar
  17. 17.
    N. Hazeri, S.S. Sajadikhah, M.T. Maghsoodlou, M. Norouzi, M. Moein, S. Mohamadian-Souri, J. Chem. Res. 37, 550 (2013)CrossRefGoogle Scholar
  18. 18.
    H. Singh, J.K. Rajput, J. Mater. Sci. 53, 3163 (2018)CrossRefGoogle Scholar
  19. 19.
    B.B.F. Mirjalilia, R. Araqia, S.A. Mohajeri, Iran J. Catal. 9, 11 (2019)Google Scholar
  20. 20.
    M. Bavadi, K. Niknam, Mol. Divers. 22, 561 (2018)CrossRefGoogle Scholar
  21. 21.
    J.N. Zhang, X.H. Yang, W.J. Guo, B. Wang, Z.H. Zhang, Synlett 28, 734 (2017)CrossRefGoogle Scholar
  22. 22.
    F. Mohamadpour, Polycycl. Aromat. Comp. (2019)Google Scholar
  23. 23.
    F. Mohamadpour, M. Lashkari, J. Serb. Chem. Soc. 83, 673 (2018)CrossRefGoogle Scholar
  24. 24.
    F. Mohamadpour, Org. Prep. Proced. Int. (2019)Google Scholar

Copyright information

© Springer Nature B.V. 2020

Authors and Affiliations

  1. 1.School of EngineeringApadana Institute of Higher EducationShirazIran

Personalised recommendations