12-tungstosilicic acid supported on different carriers: Pronounced catalytic activity in the synthesis of bis(indolyl)methanes under solvent-free conditions

Synthetic Communications

Volumn 41, Issue 3, 2011, Pages 459-467

  Rafiee, Ezzat ^a,b   Zolfagharifar, Zohre ^a   Joshaghani, Mohammad ^a,b   Eavani, Sara ^a  

^a RAZI UNIVERSITY   (Iran)

^b Kermanshah Oil Refining Company   (Iran)

Author keywords

12 tungstosilicic acid; Bis(indolyl)methanes; indole; solvent free conditions; supported catalysts

Indexed keywords

12 TUNGSTOSILICIC ACID; ALDEHYDE; BIS(INDOLYL)METHANE DERIVATIVE; CYCLOHEXANONE; METHANE; SILICIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; ELECTROPHILICITY; FILTRATION; PURIFICATION; REACTION TIME; SUBSTITUTION REACTION;

EID: 78751480342     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911003590196     Document Type: Article

References (28)

1. Bifulco, G.; Bruno, I.; Riccio, R.; Lavayre, J.; Bourdy, G. Further brominated bis- and tris-indole alkaloids from the deep-water new caledonian marine sponge Orina sp. J. Nat. Prod. 1995, 58, 1254-1260.
2. Zeligs, M. A. Diet and estrogen status: The cruciferous connection. J. Med. Food. 1998, 1, 67-82.
3. Babu, G.; Sridhar, N.; Perumal, P. T. A convenient method of synthesis of bis-indolylmethanes: Indium trichloride-catalyzed reactions of indole with aldehydes and Schiff's bases. Synth. Commun. 2000, 30, 1609-1614.
4. Chen, D.; Yu, L.; Wang, P. G. Lewis acid-catalyzed reactions in protic media: Lanthanide-catalyzed reactions of indoles with aldehydes or ketones. Tetrahedron Lett. 1996, 37, 4467-4470.
5. Nagrajan, R.; Perumal, P. T. Potassium hydrogen sulfate-catalyzed reactions of indoles: A mild, expedient synthesis of bis-indolylmethanes. Chem. Lett. 2004, 33, 288-290.
6. Chakrabarty, M.; Ghosh, N.; Basak, R.; Harigaya, Y. Dry reaction of indoles with carbonyl compounds on montmorillonite K10 clay: A mild, expedient synthesis of diindolylalkanes and vibrindole A. Tetrahedron Lett. 2002, 43, 4075-4078.
7. Reddy, A. V.; Ravinder, K.; Reddy, V. L. N.; Goud, T. V.; Ravikant, V.; Venkateswarlu, Y. Zeolite catalyzed synthesis of bis(indolyl) methanes. Synth. Commun. 2003, 33, 3687-3694.
8. 3]-catalyzed condensations of indole with carbonyl compounds. Synlett. 2005, 337-339.
9. Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. Silica-supported sodium hydrogen sulfate and amberlyst-15: Two efficient heterogeneous catalysts for facile synthesis of bis- and tris(1H-indol-3-yl)methanes from indoles and carbonyl compounds. Adv. Synth. Catal. 2003, 345, 557-559.
10. Singh, P. R.; Singh, D. U.; Samant, S. D. Sulphamic acid-A mild, efficient, and cost-effective solid acid catalyst for the synthesis of bis(1H-indol-3-yl)methanes. Synth. Commun. 2005, 35, 2133-2138.
11. Li, W. J.; Lin, X. F.; Wang, J.; Li, G. L.; Wang, Y. G. A mild and efficient synthesis of bis-indolylmethanes catalyzed by sulfamic acid. Synth. Commun. 2005, 35, 2765-2769.
12. Li, J. T.; Dai, H. G.; Xu, W. Z.; Li, T. S. An efficient and practical synthesis of bis(indolyl)methanes catalyzed by aminosulfonic acid under ultrasound. Ultrason. Sonochem. 2006, 13, 24-27.
13. Zhang, Z. H.; Yin, L.; Wang, Y. M. An efficient and practical process for the synthesis of bis(indolyl)methanes catalyzed by zirconium tetrachloride. Synthesis 2005, 1949-1954.
14. Karthik, M.; Tripathi, A. K.; Gupta, N. M.; Palanichami, M.; Murugesan, V. Zeolite catalyzed-electrophilic substitution reaction of indoles with aldehydes: Synthesis of bis(indolyl)methanes. Catal. Commun. 2004, 5, 371-375.
15. 40), a versatile and a highly water-tolerant green Lewis acid catalyzes efficient preparation of indole derivatives. J. Mol. Catal. A: Chem. 2006, 244, 168-172.
16. Azizi, N.; Torkian, L.; Saidi, M. R. Highly efficient synthesis of bis(indolyl)methanes in water. J. Mol. Catal. A: Chem. 2007, 275, 109-112.
17. Heravi, M. M.; Bakhtiari, K.; Fatehi, A.; Bamoharram, F. F. A convenient synthesis of bis(indolyl)methanes catalyzed by diphosphooctadecatungstic acid, Catal. Commun. 2008, 9, 289-292.
18. Satam, J. R.; Parghi, K. D.; Jayaram, R. V. 12-Tungstophosphoric acid supported on zirconia as an efficient and heterogeneous catalyst for the synthesis of bis(indolyl)-methanes and tris(indolyl)methanes. Catal. Commun. 2008, 9, 1071-1078.
19. Misono, M. Unique acid catalysis of heteropoly compounds (heteropolyoxometalates) in the solid state. Chem. Commun. 2001, 1141-1153.
20. Rafiee, E.; Joshaghani, M.; Eavani, S.; Rashidzadeh, S. A revision for the synthesis of b-enaminones in solvent free conditions: Efficacy of different supported heteropoly acids as active and reusable catalysts. Green Chem. 2008, 10, 982-989.
21. Rafiee, E.; Mahdavi, H.; Eavani, S.; Joshaghani, M.; Shiri, F. Catalytic activity of tungstophosphoric acid supported on carriers of diverse acidity in the synthesis of enaminones. Appl. Catal. A: Gen. 2009, 352, 202-207.
22. Rafiee, E.; Joshaghani, M.; Tork, F.; Fakhri, A.; Eavani, S. Esterification of mandelic acid catalyzed by heteropoly acid. J. Mol. Catal. A: Chem. 2008, 283, 1-4.
23. Kozhevnikova, E. F.; Rafiee, E.; Kozhevnikov, I. V. Fries rearrangement of aryl esters catalysed by heteropoly acid: Catalyst regeneration and reuse. Appl. Catal. A: Gen. 2004, 260, 25-34.
24. Cid, R.; Pecci, G. Potentiometric method for determining the number and relative strength of acid sites in colored catalysts. Appl. Catal. 1985, 14, 15-21.
25. Rafiee, E.; Eavani, S.; Rashidzadeh, S.; Joshaghani, M. Tungstophosphoric acid supported on titania as an eco-friendly, green, and reusable catalyst for the solvent-free Hantzsch multicomponent condensation. Heterocycles 2008, 75, 2225-2234.
26. Ji, S. J.; Wang, S. Y.; Zhang, Y.; Loh, T. P. Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions. Tetrahedron 2004, 60, 2051-2055.
27. Zolfigol, M. A.; Salehi, P.; Shiri, M.; Tanbakouchian, Z. A new catalytic method for the preparation of bis-indolyl and tris-indolyl methanes in aqueous media. Catal. Commun. 2007, 8, 173-178.
28. Pore, D. M.; Desai, U. V.; Thopate, T. S.; Wadgaonkar, P. P. A mild, expedient, solvent- less synthesis of bis(indolyl)alkanes using silica sulfuric acid as a reusable catalyst. Arkivoc 2008, 75-80.