Skip to main content
SpringerLink
Log in

A novel one-pot synthesis of symmetric dialkyl 2,5-bis((2,6-dimethylphenyl)imino)-2,5-dihydrofuran-3,4-dicarboxylate derivatives

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

Abstract

An efficient one-pot, three-component synthesis of symmetric dialkyl 2,5-bis((2,6-dimethylphenyl)imino)-2,5-dihydrofuran-3,4-dicarboxylate derivatives is described. The advantages of the method are high bond-forming efficiency, simple operation, and high yield.

Graphical Abstract

 

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

Scheme 1
Fig. 1
Scheme 2

Similar content being viewed by others

References

  1. L. el Kaïm, L. Grimaud, Mol. Divers. 14, 855 (2010)

    Article  Google Scholar 

  2. M. Passerini, Gazz. Chim. Ital. 51(II), 126 (1921)

    CAS  Google Scholar 

  3. I. Ugi, R. Meyer, U. Fitzer, C. Steinbrucker, Angew. Chem. 71, 386 (1959)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  5. B. Du, G. Cai, B. Zhao, X. Meng, X. Wang, Y. Li, Res. Chem. Intermed. (2012). doi:10.1007/s11164-012-0688-5

  6. X.M. Wang, H.L. Ye, Z.J. Qaun, X.C. Wang, Res. Chem. Intermed. (2012). doi:10.1007/s11164-012-0762-z

  7. M.A.P. Martins, C.P. Frizzo, D.N. Moreira, L. Buriol, O. Machado, Chem. Rev. 109, 4140 (2009)

    Article  CAS  Google Scholar 

  8. B.H. Lipshutz, Chem. Rev. 86, 795 (1986)

    Article  CAS  Google Scholar 

  9. K. Nakanish, Natural Products Chemistry (Kodansha, Tokyo, 1974)

    Google Scholar 

  10. V. Dider, L. Liang, Synth. Commun. 33, 1575 (2003)

    Article  Google Scholar 

  11. Y. Tany, C. Li, Tetrahedron Lett. 47, 3823 (2006)

    Article  Google Scholar 

  12. B. Beck, M. Magnin-Lachaux, E. Herdtweck, A. Domling, Org. Lett. 3, 2875 (2001)

    Article  CAS  Google Scholar 

  13. Y.S. Roa, Chem. Rev. 76, 625 (1976)

    Article  Google Scholar 

  14. Y.S. Roa, Chem. Rev. 64, 353 (1964)

    Article  Google Scholar 

  15. L. Zeng, Q. Ye, G. Oberlis, N.H. Shi, K.H. Gu, J.L. Mclaughlin, J. Nat. Prod. Rep. 13, 275 (1996)

    Article  CAS  Google Scholar 

  16. G.B. Payne, U.S. Patent, 3177224 (1965). Chem. Abstr. 63, 6866e (1965)

    Google Scholar 

  17. R. Huisgen, Proc. Chem. Soc. 357 (1961)

  18. N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Korassani, M. Ziyadini, G. Marandi, K. Khandan-Barani, H.R. Bijanzadeh, Arkivoc xiii, 34 (2007)

    Article  Google Scholar 

  19. M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, G. Marandi, M. Nassiri, J. Heterocycl. Chem. 43, 481 (2006)

    Article  CAS  Google Scholar 

  20. M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, G. Marandi, M. Nassiri, Synth. Commun. 35, 2771 (2005)

    Article  CAS  Google Scholar 

  21. V. Nair, A.U. Vinod, N. Abhilash, R.S. Menon, V. Santhi, R.L. Varma, S. Viji, S. Mathew, R. Srinivas, Tetrahedron 59, 10279 (2003)

    Article  CAS  Google Scholar 

  22. V. Nair, A.U. Vinod, J.S. Nair, A.R. Sreekanth, N.P. Rath, Tetrahedron Lett. 41, 6675 (2000)

    Article  CAS  Google Scholar 

  23. K. Khandan-Barani, M.T. Maghsoodlou, S.M. Habibi-Korassani, N. Hazeri, S.S. Sajadikhah, J. Chem. Res. 231 (2011)

  24. G. Marandi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, N.A. Torbati, F. Rostami Charati, B.W. Skeleton, M. Makha, Mol. Divers. 15, 197 (2011)

    Article  CAS  Google Scholar 

  25. M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, M. Ziyadini, G. Marandi, K. Khandan-Barani, P. Ebrahimi, F. Rostami Charati, A. Sobolev, M. Makha, J. Heterocycl. Chem. 46, 843 (2009)

    Article  CAS  Google Scholar 

  26. I. Yavari, A. Shaabani, M.T. Maghsoodlou, Monatsh. Chem. 128, 697 (1997)

    Article  CAS  Google Scholar 

  27. K. Zhang, P.R. Chopade, J. Louie, Tetrahedron Lett. 49, 4306 (2008)

    Article  CAS  Google Scholar 

  28. K. Kanno, S. Ren, Y. Li, K. Nakajima, T. Takahashi, Tetrahedron Lett. 48, 9199 (2007)

    Article  CAS  Google Scholar 

  29. A. Alizadeh, E. Sheikhi, Tetrahedron Lett. 48, 4887 (2007)

    Article  CAS  Google Scholar 

  30. Ullmann’s Encycl. Tech. Chem. 9, 1 (1957)

    Google Scholar 

  31. S. Ozaki, Chem. Rev. 72, 457 (1972)

    Article  Google Scholar 

  32. G. L’abbé, Synthesis 525 (1987)

  33. K. Khandan-Barani, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.S. Sajadikhah, Arkivoc xi, 22 (2011)

    Article  Google Scholar 

  34. A. Alizadeh, S. Rostamnia, N. Zohreh, H. Bijanzadeh, Monatsh. Chem. 139, 49 (2008)

    Article  CAS  Google Scholar 

  35. I. Ugi, Isonitrile Chemistry (Academic Press, London, 1971)

    Google Scholar 

  36. I. Ugi, Angew. Chem. Int. Ed. Engl. 21, 810 (1982)

    Article  Google Scholar 

Download references

Acknowledgments

We are much obliged to the Research Council of the University of Sistan and Baluchestan for financial support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, The University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran

    Malek Taher Maghsoodlou, Nourallah Hazeri & Sayyed Mostafa Habibi-Khorasani

  2. Department of Chemistry, Zahedan Branch, Islamic Azad University, Zahedan, Iran

    Khatereh Khandan-Barani

  3. Research School of Chemistry, Australian National University, Canberra, ACT, 0200, Australia

    Anthony C. Willis

Authors
  1. Malek Taher Maghsoodlou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Khatereh Khandan-Barani
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nourallah Hazeri
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sayyed Mostafa Habibi-Khorasani
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Anthony C. Willis
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Malek Taher Maghsoodlou.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Maghsoodlou, M.T., Khandan-Barani, K., Hazeri, N. et al. A novel one-pot synthesis of symmetric dialkyl 2,5-bis((2,6-dimethylphenyl)imino)-2,5-dihydrofuran-3,4-dicarboxylate derivatives. Res Chem Intermed 40, 779–785 (2014). https://doi.org/10.1007/s11164-012-1002-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-1002-2

Keywords

Search

Navigation