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
Similar content being viewed by others
References
Heeres J, Backx LJJ, Mostmans JH, Van Cutsem J (1979) J Med Chem 22:1003
Hunkeler W, Mohler H, Pieri L, Polc P, Bonetti EP, Cumin R, Schaffner R, Haefely W (1981) Nature 290:514
Brimblecombe RW, Duncan WAM, Durant GJ, Emmett JC, Ganellin CR, Parons ME (1975) J Int Med Res 3:86
Tanigawara Y, Aoyama N, Kita T, Shirakawa K, Komada F, Kasuga M, Okumura K (1999) Clin Pharmacol Ther 66:528
Wauquier A, Van Den Broeck WAE, Verheyen JL, Janssen PA (1978) J Eur J Pharmacol 47:367
Antolini M, Bozzoli A, Ghiron C, Kennedy G, Rossi T, Ursini A (1999) Bioorg Med Chem Lett 9:1023
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
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
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
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
Schmierer R, Mildenberger H, Buerstell H (1987) Patent DE361464
Schmierer R, Mildenberger H, Buerstell H (1988) Chem Abstr 108:37838
Maier T, Schmierer R, Bauer K, Bieringer H, Buerstell H, Sachse B (1989) US Patent 4820335
Maier T, Schmierer R, Bauer K, Bieringer H, Buerstell H, Sachse B (1989) Chem Abstr 111:19494
Radziszewski B (1882) Chem Ber 15:1493
Japp FR, Robinson HH (1882) Chem Ber 15:1268
Balalaie S, Arabanian A (2002) Green Chem 2:274
Kidwai M, Mothsra P, Bansal V, Somvanshi RK, Ethayathulla AS, Dey S, Singh TP (2007) J Mol Catal A Chem 265:177
Kantevari S, Vuppalapati SVN, Biradar DO, Nagarapu L (2007) J Mol Catal A Chem 266:109
Heravi MM, Derikvand F, Bamoharram FF (2007) J Mol Catal A Chem 263:112
Nagarapu L, Apuri S, Kantevari S (2007) J Mol Catal A Chem 266:104
Karimi AR, Alimohammadi Z, Azizian J, Mohammadi AA, Mohammadizadeh MR (2006) Catal Commun 7:728
Samai S, Nandi GC, Singh P, Singh MS (2009) Tetrahedron 65:10155
Heravi MM, Derikvand F, Haghighi M (2008) Monatsh Chem 139:31
Sadeghi B, Mirjalili BBF, Hashemi MM (2008) Tetrahedron Lett 49:2575
Karimi AR, Alimohammadi Z, Amini MM (2009) Mol Divers. doi:10.1007/s11030-009-9197-x
Balalaie S, Hashemi MM, Akhbari M (2003) Tetrahedron Lett 44:1709
Lantos I, Zhang WY, Shui X, Eggleston DS (1993) J Org Chem 58:7092
Davidson D, Weiss M, Jelling M (1937) J Org Chem 2:319
Kidwai M, Mothsra P (2006) Tetrahedron Lett 47:5029
US Department of Agriculture (2004) TAP report for ferric phosphate
Otsuka K, Wang Y (2001) Appl Catal A 222:145
Ren T, Yan L, Zhang X, Suo J (2003) Appl Catal A 244:11
Heravi MM, Behbahani FK, Zadsirjan V, Oskooie HA (2006) Heterocycl Commun 12:369
Behbahani FK, Yektanezhad T, Khorrami RA (2010) Heterocycles 81:2313
Heravi MM, Zadsirjan V, Behbahani FK, Oskooie HA (2006) J Mol Catal A Chem 259:201
Heravi MM, Behbahani FK, Oskooie HA (2008) Chin J Chem 26:2203
Oskooie HA, Heravi MM, Sadnia A, Behbahani FK, Jannati F (2007) Chin Chem Lett 18:1357
Sharma SD, Hazarika P, Konwar D (2008) Tetrahedron Lett 49:2216
Author information
Authors and Affiliations
Corresponding author
Rights 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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-012-0724-6