Skip to main content
SpringerLink
Log in

Synthesis of imidazolium zwitterions via an efficient one-pot three-component synthetic protocol

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

An efficient protocol was developed to access a new class of imidazolium zwitterions via a one-pot three-component reaction. The reaction of 1,2-diketones, α-hydroxyl ketones, α-benzoin oximes or α-keto oximes with 2-(2-formylphenoxy)acetic acid and ammonium acetate under reflux conditions in acetic acid provided products in good yields.

Graphic 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
Scheme 2
Scheme 3
Fig. 1

Similar content being viewed by others

References

  1. S. Kirchhecker, D. Esposito, Green. Technol. Environ. Chap. 4, 53 (2014)

    Google Scholar 

  2. S. Kirchhecker, M. Antonietti, D. Esposito, Green Chem. 16, 3705 (2014)

    Article  CAS  Google Scholar 

  3. J.S. Wilkes, P. Wasserscheid, T. Welton, in Ionic Liquids in Synthesis, 2nd edn., ed. by P. Wasserscheid, T. Welton (Wiley-VCH, Weinheim, 2007), pp. 1–6

    Google Scholar 

  4. E. Urbanik, A. Zabielska-Matejuk, A. Skrzypczak, J. Pernak, Mater Org 31, 247 (1997)

    CAS  Google Scholar 

  5. D. Demberelnyamba, K.S. Kim, S. Choi, S.Y. Park, H. Lee, C.J. Kim, I.D. Yoo, Bioorg. Med. Chem. 12, 853 (2004)

    Article  CAS  Google Scholar 

  6. M. Ao, G. Xu, Y. Zhu, Y. Bai, J. Colloid Interface Sci. 326, 490 (2008)

    Article  CAS  Google Scholar 

  7. P.D. Galgano, O.A. El Seoud, J. Colloid Interface Sci. 361, 186 (2011)

    Article  CAS  Google Scholar 

  8. A.J. Arduengo, Acc. Chem. Res. 32, 913 (1999)

    Article  CAS  Google Scholar 

  9. B.E. Ketz, X.G. Ottenwaelder, R.M. Waymouth, Chem. Commun. 45, 5693 (2005)

    Article  Google Scholar 

  10. W.A. Herrmann, Angew. Chem. Int. Ed. Engl. 35, 2805 (1996)

    Article  CAS  Google Scholar 

  11. N. Fechler, T.P. Fellinger, M. Antonietti, Adv. Mater. 25, 75 (2013)

    Article  CAS  Google Scholar 

  12. V. Srivastava, J. Haque, C. Verma, P. Singh, H. Lgaz, R. Salghi, M.A. Quraishi, J. Mol. Liq. 244, 340 (2017)

    Article  CAS  Google Scholar 

  13. R. Chatterjee, S. Mahato, S. Santra, G.V. Zyryanov, A. Hajra, A. Majee, Chem. Select 3, 5843 (2018)

    CAS  Google Scholar 

  14. R. Ghadari, F. Hajishaabanha, M. Aghaei, A. Shaabani, S.W. Ng, Mol. Divers. 16, 453 (2012)

    Article  CAS  Google Scholar 

  15. R. Ghadari, F. Hajishaabanha, M. Mahyari, A. Shaabani, H.R. Khavasi, Tetrahedron Lett. 53, 4018 (2012)

    Article  CAS  Google Scholar 

  16. A. Shaabani, F. Hajishaabanha, H. Mofakham, M. Mahyari, B. Lali, Helve. Chim. Acta 95, 246 (2012)

    Article  CAS  Google Scholar 

  17. A. Shaabani, F. Hajishaabanha, M. Mahyari, H. Mofakham, S.W. Ng, Tetrahedron 67, 8360 (2011)

    Article  CAS  Google Scholar 

  18. A. Shaabani, F. Hajishaabanha, H. Mofakham, A. Maleki, Mol. Divers. 14, 179 (2010)

    Article  CAS  Google Scholar 

  19. A. Shaabani, H. Sepahvand, A. Bazgir, H.R. Khavasi, Tetrahedron 74, 7058 (2018)

    Article  CAS  Google Scholar 

  20. V.P. Mehta, S.G. Modha, E. Ruijter, K. Van Hecke, L. Van Meervelt, C. Pannecouque, J. Balzarini, R.V.A. Orru, E. Van der Eycken, J. Org. Chem. 76, 2828 (2011)

    Article  CAS  Google Scholar 

  21. L. Shi, L. Hu, J. Wang, X. Cao, H. Gu, Org. Lett. 14, 1876 (2012)

    Article  CAS  Google Scholar 

  22. K. Siva Kumar, P. Mahesh Kumar, K. Anil Kumar, M. Sreenivasulu, A.A. Jafar, D. Rambabu, G. Rama Krishna, C. Malla Reddy, R. Kapavarapu, K. Shivakumar, K. Krishna Priya, K.V.L. Parsa, M. Pal, Chem. Commun. 47, 5010 (2011)

    Article  Google Scholar 

  23. M. Weiss, J. Am. Chem. Soc. 74, 200 (1952)

    Article  CAS  Google Scholar 

  24. D. Davidson, J. Am. Chem. Soc. 58, 1821 (1936)

    Article  CAS  Google Scholar 

  25. D. Davidson, E. Epstein, J. Org. Chem. 1, 305 (1936)

    Article  CAS  Google Scholar 

  26. B. Kaboudin, F. Saadati, Heterocycles 65, 353 (2005)

    Article  CAS  Google Scholar 

  27. M. Heidari, M. Rezaei, R. Badri, Heterocycl. Commun. 21, 73 (2015)

    Article  CAS  Google Scholar 

  28. A. Shaabani, A. Rahmati, J. Mol. Catal. A Chem. 249, 246 (2006)

    Article  CAS  Google Scholar 

  29. K. Khan, Z.N. Siddiqui, Ind. Eng. Chem. Res. 54, 6611 (2015)

    Article  CAS  Google Scholar 

  30. A. Maleki, Z. Alirezvani, J. Chil. Chem. Soc. 61, 3116 (2016)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge financial support of the Iran National Science Foundation (INSF) and the Research Council of Shahid Beheshti University. The crystallographic part was supported by the Project 18-10504S of the Czech Science Foundation using instruments of the ASTRA laboratory established within the Operation program Prague Competitiveness—Project CZ.2.16/3.1.00/24510.

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Shahid Beheshti University, G. C., P.O. Box 19396-4716, Tehran, Iran

    Fatemeh Hajishaabanha, Shabnam Shaabani, Ahmad Shaabani & Mona Hamidzad Sangachin

  2. Institute of Physics of the Czech Academy of Sciences, Na Slovance 2, 182 21, Prague, Czech Republic

    Michal Dusek & Monika Kučeráková

Authors
  1. Fatemeh Hajishaabanha
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shabnam Shaabani
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ahmad Shaabani
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mona Hamidzad Sangachin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Michal Dusek
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Monika Kučeráková
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ahmad Shaabani.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 7004 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hajishaabanha, F., Shaabani, S., Shaabani, A. et al. Synthesis of imidazolium zwitterions via an efficient one-pot three-component synthetic protocol. J IRAN CHEM SOC 17, 513–519 (2020). https://doi.org/10.1007/s13738-019-01789-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-019-01789-x

Keywords

Search

Navigation