Skip to main content
Log in

A greener route for the one-pot synthesis of 1,2,4,5-tetraarylated imidazoles

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

Abstract

An efficient synthesis of various tetraarylated imidazoles using anhydrous FePO4 as a catalyst by four-component condensation of benzil (or benzoin), aldehydes, amines, and ammonium acetate in refluxing ethanol is described.

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
Scheme 2

Similar content being viewed by others

References

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

    Article  CAS  Google Scholar 

  2. Hunkeler W, Mohler H, Pieri L, Polc P, Bonetti EP, Cumin R, Schaffner R, Haefely W (1981) Nature 290:514

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  5. Wauquier A, Van Den Broeck WAE, Verheyen JL, Janssen PA (1978) J Eur J Pharmacol 47:367

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

  8. 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 Adams JL, Young PR (1994) Nature 372:739

    Google Scholar 

  9. Takle AK, Brown MJB, 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 

  10. 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 

  11. Schmierer R, Mildenberger H, Buerstell H (1987) Patent DE361464

  12. Schmierer R, Mildenberger H, Buerstell H (1988) Chem Abstr 108:37838

  13. Maier T, Schmierer R, Bauer K, Bieringer H, Buerstell H, Sachse B (1989) US Patent 4820335

  14. Maier T, Schmierer R, Bauer K, Bieringer H, Buerstell H, Sachse B (1989) Chem Abstr 111:19494

  15. Radziszewski B (1882) Chem Ber 15:1493

    Article  Google Scholar 

  16. Japp FR, Robinson HH (1882) Chem Ber 15:1268

    Article  Google Scholar 

  17. Balalaie S, Arabanian A (2002) Green Chem 2:274

    Article  Google Scholar 

  18. Kidwai M, Mothsra P, Bansal V, Somvanshi RK, Ethayathulla AS, Dey S, Singh TP (2007) J Mol Catal A Chem 265:177

    Article  CAS  Google Scholar 

  19. Kantevari S, Vuppalapati SVN, Biradar DO, Nagarapu L (2007) J Mol Catal A Chem 266:109

    Article  CAS  Google Scholar 

  20. Heravi MM, Derikvand F, Bamoharram FF (2007) J Mol Catal A Chem 263:112

    Article  CAS  Google Scholar 

  21. Nagarapu L, Apuri S, Kantevari S (2007) J Mol Catal A Chem 266:104

    Article  CAS  Google Scholar 

  22. Karimi AR, Alimohammadi Z, Azizian J, Mohammadi AA, Mohammadizadeh MR (2006) Catal Commun 7:728

    Article  CAS  Google Scholar 

  23. Samai S, Nandi GC, Singh P, Singh MS (2009) Tetrahedron 65:10155

    Article  CAS  Google Scholar 

  24. Heravi MM, Derikvand F, Haghighi M (2008) Monatsh Chem 139:31

    Article  CAS  Google Scholar 

  25. Sadeghi B, Mirjalili BBF, Hashemi MM (2008) Tetrahedron Lett 49:2575

    Article  CAS  Google Scholar 

  26. Karimi AR, Alimohammadi Z, Amini MM (2009) Mol Divers. doi:10.1007/s11030-009-9197-x

    Google Scholar 

  27. Balalaie S, Hashemi MM, Akhbari M (2003) Tetrahedron Lett 44:1709

    Article  CAS  Google Scholar 

  28. Lantos I, Zhang WY, Shui X, Eggleston DS (1993) J Org Chem 58:7092

    Article  CAS  Google Scholar 

  29. Davidson D, Weiss M, Jelling M (1937) J Org Chem 2:319

    Article  CAS  Google Scholar 

  30. Kidwai M, Mothsra P (2006) Tetrahedron Lett 47:5029

    Article  CAS  Google Scholar 

  31. US Department of Agriculture (2004) TAP report for ferric phosphate

  32. Otsuka K, Wang Y (2001) Appl Catal A 222:145

    Article  CAS  Google Scholar 

  33. Ren T, Yan L, Zhang X, Suo J (2003) Appl Catal A 244:11

    Article  CAS  Google Scholar 

  34. Heravi MM, Behbahani FK, Zadsirjan V, Oskooie HA (2006) Heterocycl Commun 12:369

    CAS  Google Scholar 

  35. Behbahani FK, Yektanezhad T, Khorrami RA (2010) Heterocycles 81:2313

    Article  CAS  Google Scholar 

  36. Heravi MM, Zadsirjan V, Behbahani FK, Oskooie HA (2006) J Mol Catal A Chem 259:201

    Article  CAS  Google Scholar 

  37. Heravi MM, Behbahani FK, Oskooie HA (2008) Chin J Chem 26:2203

    Article  CAS  Google Scholar 

  38. Oskooie HA, Heravi MM, Sadnia A, Behbahani FK, Jannati F (2007) Chin Chem Lett 18:1357

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Farahnaz K. Behbahani.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Behbahani, F.K., Yektanezhad, T. A greener route for the one-pot synthesis of 1,2,4,5-tetraarylated imidazoles. Monatsh Chem 143, 1529–1532 (2012). https://doi.org/10.1007/s00706-012-0724-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-012-0724-6

Keywords

Navigation