Skip to main content
Log in

Squaric acid catalyzed simple synthesis of N-substituted pyrroles in green reaction media

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

An operationally simple and efficient protocol for squaric acid catalyzed synthesis of N-substituted pyrroles via the reaction of 2,5-dimethoxytetrahydrofuran and 2,5-hexandione with aryl amines in green reaction media (water, deep eutectic solvent, and polyethylene glycol) under ultrasound irradiation or thermal conditions in good to excellent yields has been developed.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1

Similar content being viewed by others

References

  1. Li CJ (2005) Chem Rev 105:3095

    Article  CAS  Google Scholar 

  2. Singh S, Lobo H, Shankarling G (2011) Catal Lett 141:178

    Article  CAS  Google Scholar 

  3. Mase N, Barbas CF (2010) Org Biomol Chem 8:4043

    Article  CAS  Google Scholar 

  4. Wang G, Sun H, Cao X, Chen L (2011) Catal Lett 141:1324

    Article  CAS  Google Scholar 

  5. Huang WB, Liu QW, Zheng L-Y, Zhang S-Q (2011) Catal Lett 141:191

    Article  CAS  Google Scholar 

  6. Ramesh K, Murthy SN, Nageswar YVD (2012) Synth Commun 42:2471

    Article  CAS  Google Scholar 

  7. Gupta RR, Kumar M, Gupta V (1999) Heterocyclic chemistry II: five-membered heterocycles. Springer, Berlin

    Google Scholar 

  8. Sawant P, Maier ME (2010) Tetrahedron 66:9738

    Article  CAS  Google Scholar 

  9. Estevez V, Villacampa M, Menendez JC (2012) Chem Soc Rev 39:4402

    Article  Google Scholar 

  10. Bandyopadhyay D, Mukherjee S, Banik BK (2010) Molecules 15:2520

    Article  CAS  Google Scholar 

  11. Zhu F-X, Li H-X, Wang W (2011) J Am Chem Soc 133:11632

    Article  CAS  Google Scholar 

  12. Abid M, Spaeth A, Török B (2006) Adv Synth Catal 348:2191

    Article  CAS  Google Scholar 

  13. Banik BK, Banik I, Renteria M, Dasgupta SK (2005) Tetrahedron Lett 46:2643

    Article  CAS  Google Scholar 

  14. Banik BK, Samajdar S, Banik I (2004) J Org Chem 69:213

    Article  CAS  Google Scholar 

  15. Chen J, Wu H, Zheng Z, Jin C, Zhang X, Su W (2006) Tetrahedron Lett 47:5383

    Article  CAS  Google Scholar 

  16. Minetto G, Raveglia LF, Taddei M (2004) Org Lett 6:389

    Article  CAS  Google Scholar 

  17. Polshettiwar V, Baruwati B, Varma RS (2009) Chem Commun 1837

  18. Polshettiwar V, Varma RS (2010) Tetrahedron 66:1091

    Article  CAS  Google Scholar 

  19. Song G, Wang B, Wang G, Kang Y, Yang T, Yang L (2005) Synth Commun 35:1051

    Article  CAS  Google Scholar 

  20. Bandyopadhyay D, Mukherjee S, Banik BK, Granados JC, Short JD (2012) Eur J Med Chem 50:209

    Article  CAS  Google Scholar 

  21. Wang B, Gu Y, Luo C, Yang T, Yang L, Suo J (2004) Tetrahedron Lett 45:3417

    Article  CAS  Google Scholar 

  22. Azizi N, Khajeh-Amiri A, Ghafuri H, Bolourtchian M, Saidi MR (2009) Synlett 14:2245

    Article  Google Scholar 

  23. Wilson MA, Filzen G, Welmaker GS (2009) Tetrahedron Lett 50:4807

    Article  CAS  Google Scholar 

  24. Yadav JS, Reddy BVS, Eeshwaraiah B, Gupta MK (2004) Tetrahedron Lett 45:5873

    Article  CAS  Google Scholar 

  25. Zhang X, Shi J (2011) Tetrahedron 67:898

    Article  CAS  Google Scholar 

  26. Rivera S, Bandyopadhyay D, Banik BK (2009) Tetrahedron Lett 50:5445

    Article  CAS  Google Scholar 

  27. Azizi N, Saidi MR (2005) Org Lett 7:3649

    Article  CAS  Google Scholar 

  28. Azizi N, Torkiyan L, Saidi MR (2006) Org Lett 8:2079

    Article  CAS  Google Scholar 

  29. Azizi N, Aryanasab F, Torkiyan L, Ziyaei A, Saidi MR (2006) J Org Chem 71:3634

    Article  CAS  Google Scholar 

  30. Storer RI, Aciro C, Jones LH (2011) Chem Soc Rev 40:2330

    Article  Google Scholar 

Download references

Acknowledgments

The financial support of this work was provided by the Iran National Science Foundation (INSF) and is gratefully appreciated.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Najmadin Azizi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Azizi, N., Davoudpour, A., Eskandari, F. et al. Squaric acid catalyzed simple synthesis of N-substituted pyrroles in green reaction media. Monatsh Chem 144, 405–409 (2013). https://doi.org/10.1007/s00706-012-0841-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-012-0841-2

Keywords

Navigation