Skip to main content
SpringerLink
Log in

Trichloroisocyanuric acid-catalyzed one-pot synthesis of 2,4,5-trisubstituted imidazoles

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

Abstract

Trichloroisocyanuric acid was found to be a highly efficient homogeneous catalyst for synthesis of imidazoles via one-pot, three-component condensation of aldehydes with benzil and ammonium acetate. The valuable advantages of this method are high yields of products, easy work-up and purification procedure, and use of a commercially available, inexpensive, and non-volatile catalyst.

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
Scheme 2

Similar content being viewed by others

References

  1. Zhu J, Bienayme H (2005) Multicomponent reactions. Wiley–VCH, Weinheim

    Book  Google Scholar 

  2. Domling A (2006) Chem Rev 106:17

    Article  Google Scholar 

  3. Weber L (2002) Drug Discov Today 7:143

    CAS  Google Scholar 

  4. Tempest PA (2005) Curr Opin Drug Discov Dev 8:776

    CAS  Google Scholar 

  5. Cook AH, Jones DG (1941) J Chem Soc 278

  6. Heeres J, Backx LJJ, Mostmans JH, Van Cutsem J (1979) J Med Chem 22:1003

    Article  CAS  Google Scholar 

  7. Tanigawara Y, Aoyama N, Kita T, Shirakawa K, Komada F, Kasuga M, Okumura K (1999) Clin Pharmacol Ther 66:528

    Article  CAS  Google Scholar 

  8. Brimblecombe RW, Duncan WAM, Durant GJ, Cemmett JC, Ganellin CR, Parsons ME (1975) J Int Med Res 3:86

    CAS  Google Scholar 

  9. Dorneanu O, Popovici I, Boiculese L, Popovici I, Bosnea DJ (2003) Preventive Med 11:41

    Google Scholar 

  10. Dinh HT, Kernbaum S, Frottier J (1978) Lancet 3111:338

    Article  Google Scholar 

  11. Lee JC, Laydon JT, McDonnell PC, Gallagher TF, Kumar S, Green D, McNulty D, Blumenthal MJ, Keys JR, Vatter SWL, Strickler JE, Mclaughlin MM, Siemens IR, Fisher SM, Livi GP, White JR, Adams JL, Young PR (1994) Nature 372:739

    Article  CAS  Google Scholar 

  12. Takle AK, Brown MJ, Davies S, Dean DK, Francis G, Gaiba A, Hird AW, King FD, Lovell PJ, Naylor A, Reith AD, Steadman JG, Wilson DM (2006) Bioorg Med Chem Lett 16:378

    Article  CAS  Google Scholar 

  13. de Laszlo SE, Hacker C, Li B, Kim D, MacCoss M, Mantalo N, Pivnichny JV, Colwell L, Koch GE, Cascieri MA, Hagmenn WK (1999) Bioorg Med Chem Lett 9:641

    Article  Google Scholar 

  14. Schmierer R, Mildenberger H, Buerstell H (1987) German Patent 361464; (1988) Chem Abstr 108:37838

  15. Maier T, Schmierer R, Bauer K, Bieringer H, Buerstell H, Sachse B (1989) US Patent 4820335; (1989) Chem Abstr 111:19494W

  16. Antolini M, Bozzoli A, Ghiron C, Kennedy G, Rossi T, Ursini A (1999) Bioorg Med Chem Lett 9:1023

    Article  CAS  Google Scholar 

  17. Wang L, Woods KW, Li Q, Barr KJ, McCroskey RW, Hannick SM, Gherke L, Credo RB, Hui Y-H, Marsh K, Warren R, Lee JY, Zielinsky-Mozng N, Frost D, Rosenberg SH, Sham HL (2002) J Med Chem 45:1697

    Article  CAS  Google Scholar 

  18. Lombandine JG, Wiseman EH (1974) J Med Chem 17:1182

    Article  Google Scholar 

  19. Wasserschied P, Keim W (2000) Angew Chem Int Ed 39:3772

    Article  Google Scholar 

  20. Chowdhurg S, Mohan RS, Scott JL (2007) Tetrahedron 63:2363

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  22. Sharma SD, Hazarika P, Konwar D (2008) Tetrahedron Lett 49:2216

    Article  Google Scholar 

  23. Sangshetti JN, Kokare ND, Kotharkara SA, Shinde DB (2008) J Chem Sci 120:463

    Article  CAS  Google Scholar 

  24. Heravi MM, Bakhtiari K, Oskooie HA, Taheri S (2007) J Mol Catal A Chemical 263:279

    Article  CAS  Google Scholar 

  25. Wang LM, Wang YH, Tian H, Yao YF, Shao JH, Liu B (2006) J Fluorine Chem 127:1570

    Article  CAS  Google Scholar 

  26. Siddiqui SA, Narkhede UC, Palimkar SS, Daniel T, Loholi RJ, Srinivasan KV (2005) Tetrahedron 61:3539

    Article  CAS  Google Scholar 

  27. Khosropour AR (2008) Ultrason Sonochem 15:659

    Article  CAS  Google Scholar 

  28. Balalaie S, Arabanian A (2000) Green Chem 2:274

    Article  CAS  Google Scholar 

  29. Chattaway FD, Wadmore JM (1902) J Chem Soc 81:191

    Article  CAS  Google Scholar 

  30. Kolvari E, Ghorbani-Choghamarani A, Salehi P, Shirini F, Zolfigol MA (2007) J Iran Chem Soc 4:126

    Article  CAS  Google Scholar 

  31. Bigdeli MA, Nemati F, Mahdavinia GH, Doostmohammadi H (2009) Chin Chem Lett 20:1275

    Article  CAS  Google Scholar 

  32. Bigdeli MA, Jafari S, Mahdavinia GH, Hazarkhani H (2007) Catal Commun 8:1641

    Article  CAS  Google Scholar 

  33. Veisi H, Gholbedaghi R, Malakootikhah J, Sedrpoushan A, Maleki B, Kordestani D (2010) J Heterocycl Chem 47:1398

    Article  CAS  Google Scholar 

  34. Khazaei A, Zolfigol MA, Rostami A, Ghorbani-Choghamarani A (2007) Catal Commun 8:543

    Article  CAS  Google Scholar 

  35. Zolfigol MA, Khazaei A, Ghorbani-Choghamarani A, Rostami A, Hajjami M (2006) Catal Commun 7:399

    Article  CAS  Google Scholar 

  36. Shen M-G, Cai C, Yi W-B (2008) J Flurine Chem 129:541

    Article  CAS  Google Scholar 

  37. Joshi RS, Mandhane PG, Shaikh MU, Kale RP, Gill CH (2010) Chin Chem Lett 21:429

    Article  CAS  Google Scholar 

  38. White DM, Sonnenberg J (1964) J Org Chem 29:192

    Google Scholar 

  39. Safari J, Khalili SD, Banitaba SH (2011) Synth Commun 41:2359

    Article  CAS  Google Scholar 

  40. Goswami S, Chakrabarty R (2011) Eur J Chem 2:410

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the Research Council of Hakim Sabzevari University for the financial support of this work.

Author information

Authors and Affiliations

  1. Department of Chemistry, Hakim Sabzevari University, Sabzevar, Iran

    Seyedeh Fatemeh Hojati, Seyede Atefe Nezhadhoseiny & Zahra Beykzadeh

Authors
  1. Seyedeh Fatemeh Hojati
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Seyede Atefe Nezhadhoseiny
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zahra Beykzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Seyedeh Fatemeh Hojati.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material (DOC 20 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hojati, S.F., Nezhadhoseiny, S.A. & Beykzadeh, Z. Trichloroisocyanuric acid-catalyzed one-pot synthesis of 2,4,5-trisubstituted imidazoles. Monatsh Chem 144, 387–390 (2013). https://doi.org/10.1007/s00706-012-0830-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-012-0830-5

Keywords

Search

Navigation