Abstract
Bis(indoyl)methanes have been synthesized in excellent yields in the presence of catalytic amount of Cu1.5PMo12O40 in molten tetraethylammonium chloride as an ionic liquid. The catalyst is recovered and recycled.
Similar content being viewed by others
References
Sundberg RJ (1996) The chemistry of indoles. Academic Press, New York
Karthik M, Tripathi AK, Gupta NM, Palanichamy M, Murugesan V (2004) Zeolite catalyzed electrophilic substitution reaction of indoles with aldehydes: synthesis of bis(indolyl)methanes. Catal Commun 5: 371–375. doi:10.1016/j.catcom.2004.04.007
Babu G, Sridhar N, Perumal PT (2000) A convenient method of synthesis of bis-indolylmethanes: indium trichloride catalyzed reactions of indole with aldehydes and Schiff’s bases. Synth Commun 30: 1609–1614. doi:10.1080/00397910008087197
Nagarajan R, Perumal PT (2002) Electrophilic substitution of indoles catalyzed by triphenyl phosphonium perchlorate: synthesis of 3-acetyl indoles and bis-indolylmethane derivatives. Synth Commun 32: 105–109. doi:10.1081/SCC-120001515
Chakrabary M, Sarkar S (2002) Novel clay-mediated, tandem addition–elimination-(Michael) addition reactions of indoles with 3-formylindole: an eco-friendly route to symmetrical and unsymmetrical triindolylmethanes. Tetrahedron Lett 43: 1351–1353. doi:10.1016/S0040-4039(01)02380-2
Koshima H, Matsuaka W (2002) N-bromosuccinimide catalyzed condensations of indoles with carbonyl compounds under solvent-free conditions. J Heterocycl Chem 39: 1089–1091
Bandger BP, Shaikh AK (2003) Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions. Tetrahedron Lett 44: 1959–1961. doi:10.1016/S0040-4039(03)00032-7
Nagarajan R, Perumal PT (2004) Potassium hydrogen sulfate-catalyzed reactions of indoles: a mild, expedient synthesis of bis-indolylmethanes. Chem Lett 33: 288–289. doi:10.1246/cl.2004.288
Wang LM, Han J, Tian H, Sheng J, Fan ZY, Tang XP. (2005) Rare earth perfluorooctanoate [Re(PFO)3]-Catalyzed condensations of indole with carbonyl compounds. Synlett 337–339. doi:10.1055/s-2004-837210
Bandgar BP, Shaikh KA (2004) Organic reactions in aqueous media: InF 3 catalysed synthesis of bis(indolyl)methanes in water under mild conditions. J Chem Res 2004: 34–36
Nagawade RR, Shinde DB (2006) Zirconyl (IV) chloride-catalysed reaction of indoles: an expeditious synthesis of bis(indolyl)methanes. Acta Chim Slov 53: 210–213
Zhang ZH, Yin L, Wang YM (2005) An efficient and practical process for the synthesis of bis(indolyl)methanes catalyzed by zirconium tetrachloride. Synthesis 12: 1949–1954
Gu DG, Jun JS, Qin JZ, Feng ZM, Peng LT (2005) An efficient synthesis of bis(indolyl)methanes catalyzed by recycled acidicionic liquid. Synlett 959–962
Chen D, Yu L, Wang PG (1996) Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones. Tetrahedron Lett 37: 4467–4470. doi:10.1016/0040-4039(96)00958-6
Mi X, Luo S, He J, Cheng JP (2004) Dy(OTf)3 in ionic liquid: an efficient catalytic system for reactions of indole with aldehydes/ketones or imines. Tetrahedron Lett 45: 4567–4570. doi:10.1016/j.tetlet.2004.04.039
Khabazzadeh H, Saidi K, Sheibani H (2008) Microwave-assisted synthesis of dihydropyrimidin-2(1H)-ones using graphite supported lanthanum chloride as a mild and efficient catalyst. Bioorg Med Chem Lett 18: 278–280. doi:10.1016/j.bmcl.2007.10.087
Khabazzadeh H, Saidi K, Sheibani H (2008) Highly efficient conversion of aromatic acylals to 3, 4-dihydropyrimidinones: a new protocol for the Biginelli reaction. Arkivoc xv: 34–41
Lapidus A, Eliseev O, Bondarenko T, Stepin N (2006) Palladium catalysed hydroxycarbonylation of 1-phenylethanol in molten salt media. J Mol Catal Chem 252: 245–251. doi:10.1016/j.molcata.2006.02.061
Khodaei MM, Khosropour AR, Ghozati K (2004) A powerful, practical and chemoselective synthesis of 2-anilinoalkanols catalyzed by Bi(TFA)3 or Bi(OTf)3 in the presence of molten TBAB. Tetrahedron Lett 45: 3525–3529. doi:10.1016/j.tetlet.2004.02.139
Firouzabadi H, Iranpoor N, Jafari AA (2006) Aluminumdodecatungstophosphate (AlPW12O40), a versatile and a highly water tolerant green Lewis acid catalyzes efficient preparation of indole derivatives. J Mol Catal Chem 244: 168–172. doi:10.1016/j.molcata.2005.09.005
Srinivasa A, Varma PP, Hulikal V, Mahadevan KM (2008) Antimony (III) sulfate catalyzed condensation reaction of indoles with carbonyl compounds. Monatsh Chem 139: 111–115. doi:10.1007/s00706-007-0697-z
Niknam K, Zolfigol MA, Sadabadi T, Nejati A (2006) Preparation of indolylmethanes catalyzed by metal hydrogen sulfates. J Iran Chem Soc 3: 318–322
Hasaninejad A, Zare A, Sharghi H, Niknam K, Shekouhy M (2007) P2O5/SiO2 as an efficient, mild, and heterogeneous catalytic system for the condensation of indoleswith carbonyl compounds under solvent-free conditions. Arkivoc xiv: 39–50
Allaoui LA, Aouissi A (2006) Effect of the Brønsted acidity on the behavior of CO2 methanol reaction. J Mol Catal Chem 259: 281–285. doi:10.1016/j.molcata.2006.06.034
Heravi MM, Bakhtiari K, Fatehi A, Bamoharram FF (2008) A convenient synthesis of bis(indolyl)methanes catalyzed by diphosphooctadecatungstic acid. Catal Commun 9: 289–292. doi:10.1016/j.catcom.2007.07.039
Azizi N, Torkian L, Saidi MR (2007) Highly efficient synthesis of bis(indolyl)methanes in water. J Mol Catal Chem 275: 109–112. doi:10.1016/j.molcata.2007.05.024
Bandgar BP, Bettigeri SV, Joshi NS (2004) Hexamethylenetetraamine-bromine catalyzed rapid and efficient synthesis of bis(indolyl)methanes. Monatsh Chem 135: 1265–1275. doi:10.1007/s00706-004-0206-6
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Seyedi, N., Khabazzadeh, H. & Saidi, K. Cu1.5PMo12O40 as an efficient, mild and heterogeneous catalyst for the condensation of indole with carbonyl compounds. Mol Divers 13, 337–342 (2009). https://doi.org/10.1007/s11030-009-9120-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11030-009-9120-5