An efficient one-pot synthesis of BIS (indolyl)methanes catalyzed by ionic liquid with multi-SO3 H groups under ambient temperature in water

World Applied Sciences Journal

Volumn 15, Issue 6, 2011, Pages 877-884

  Vahdat, Seyed Mohammad ^a   Khaksar, Samad ^a   Baghery, Saeed ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Bis(indolyl)methanes; Chemoselective; Groups; Indole; Ionic liquid with multi SO3H; Water solvent

Indexed keywords

EID: 81555195409     PISSN: 18184952     EISSN: 19916426     Source Type: Journal    
DOI: None     Document Type: Article

References (43)

1. Riccio, R., G. Bifulco and I. Bruno, 1995. Further brominated bis- and tris-indole alkaloidsfrom the deep-water new caledonian marine sponge Orina sp. J. Nat. Prod. 58: 1254-1260.
2. Bell, R. S. Carmelli and N. Sar, 1994. Vibrindole A, a metabolite of the marine bacterium Vibrio parahaemolyticus, isolated from toxic mucus of the boxfish Ostracion cubicus. J. Nat. Prod. 57: 1587-1590.
3. Fahy, E., B.C.M. Potts, D.J. Faulkner and K. Smith, 1991. 6-Bromotryptamine derivatives from the Gulf of California tunicate Didemnum candidum. J. Nat. Prod., 54: 564-569.
4. Glasby, J.S., 1975. Encyclopedia of the Alkaloids. Plenum Press. New York.
5. Ramirez, A. and S. Garcia-Rubio, 2003. Current progress in the chemistry and pharmacology of akuammiline alkaloids. Curr. Med. Chem., 10: 1891-1915.
6. Chakrabarty, M., N. Ghosh, R. Basak and Y. Harigaya, 2002. Dry reaction of indoles with carbonyl compounds on montmorillonite K-10 clay: a mild, expedient synthesis of diindolylalkanes and vibrindole A. Tetrahedron Lett., 43: 4075-4078.
7. Reddy, A.V., K. Ravinder, V.L.N. Reddy, T. Venkateshwer Goud, V. Ravikanth and Y. Venkateswarlu, 2003. Zeolite catalyzed synthesis of bis (indolyl) methanes. Synth. Commun., 33: 3687-3694.
8. Remers, W.A., 1972. In Houlihan WJ Heterocyclic compounds. Interscience Publishers. New York.
9. Mi, X., S. Luo, J. He and J.P. Cheng, 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.
10. Ji, S.J., M.F. Zhou, D.G. Gu, S.Y. Wang and T.P. Loh, 2003. Efficient synthesis of bis (indolyl) methanes catalyzed by Lewis acids in ionic liquids. Synlett. pp: 2077-2079.
11. Firouzabadi, H., N. Iranpoor and A.A. Jafari, 2005. Aluminumdodecatungstophosphate (AlPW12O40), a versatile and a highly water tolerant green Lewis acid catalyzes efficient preparation of indole derivatives. J. Mol. Catal. A. Chem., 244: 168-172.
12. Xia, M., S.H. Wang and W.B. Yuan, 2004. Lewis acid catalyzed electrophilic substitution of indole with aldehydes and schiff's bases under microwave solvent-free irradiation. Synth. Commun. 34: 3175-3182.
13. Zolfigol, M.A., P. Salehi, M. Shiri, A. Sayadi, A. Abdoli, H. Keypour, M. Rezaeivala, K. Niknam and E. Kolvari, 2008. A simple and efficient route for the synthesis of di and tri(bis(indolyl) methanes) as new triarylmethanes. Mol. Divers., 12: 203-207.
14. Hagiwara, H., M. Sekifuji, T. Hoshi, K. Qiao, C. Yokoyama and C. Yokoyama, 2007. Synthesis of bis(indolyl)methanes catalyzed by acidic ionic liquid immobilized on silica (ILIS). Synlett. pp: 1320-1322.
15. Sharma, G.V.M., J.J. Reddy, P.S. Lakshmi and P.R.A. Krishna, 2004. Versatile and practical synthesis of bis(indolyl)methanes/ bis (indolyl)glycoconjugates catalyzed by trichloro-1,3,5-triazine. Tetrahedron Lett., 45: 7729-7732.
16. Azizi, N., L. Torkian and M.R. Saidi, 2007. Highly efficient synthesis of bis(indolyl)methanes in water. J. Mol. Catal. A. Chem., 275: 109-112.
17. Deb, M.L. and P.J. Bhuyan, 2006. An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature. Tetrahedron Lett., 47: 1441-1443.
18. Li, C.J. and T.H. Chan, 1997. Organic reaction in aqueousemedia. Wiley. New York.
19. Khalafi-Nezhad, A. and B. Mokhtari, 2004. Tetrabutylammonium bromide: an efficient media for dimethoxytritylation of the 5'-hydroxyl function of nucleosides. Tetrahedron Lett., 45: 6737-6739.
20. Welton, T., 1999. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis. Chem. Rev. 99: 2071-2084.
21. Wasserscheid, P. and W. Keim, 2000. Ionic liquids - New ' solutions' for transition metal catalysis. Ang. Chem. Int. Ed., 39: 3772-3789.
22. Bao, S., L. Chen, Y. Ji and J. Yang, 2010. Efficient prodecure for oxathioacetalization using the novel ionic liquid. Chin. J. Chem., 28: 2119-2122.
23. Vahdat, S.M., R. Baharfar, M. Tajbakhsh, A. Heydari, S.M. Baghbanian and S. Khaksar, 2008. Organocatalytic synthesis of a-hydroxy and a-aminophosphonates Tetrahedron Lett., 49: 6501-6504.
24. Vahdat, S.M., S. Khaksar and M. Khavarpour, 2011. Oxalic acid as a simple and efficient organocatalyst for three-component synthesis of a-amino nitriles Chin. Chem. Lett., 22: 543-546.
25. Chen, D., L. Yu and P.G. Wang, 1996. Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones. Tetrahedron Lett. 37: 4467-4470.
26. Niknam, K., M.A. Zolfigol, T. Sadabadi and A. Nejati, 2006. Preparation of indolylmethanes catalyzed by metal hydrogen sulfates. J. Iran. Chem. Soc. 3: 318-322.
27. Wang, L., J.H. Han, T. Sheng, J.Z. Fan and X. Tang, 2005. Rare Earth Perfluorooctanoate [Re(PFO)3]-Catalyzed Condensations of Indole with Carbonyl Compounds. Synlett. pp: 337-339.
28. Nagarajan, R. and P.T. Perumal, 2002. InCl3 and In(OTf)3 catalyzed reactions: synthesis of 3-acetyl indoles, bis-indolylmethane and indolylquinoline derivatives. Tetrahedron. 58: 1229-1232.
29. Srinivasa, A., P.P. Varma, V. Hulikal and K.M. Mahadevan, 2008. Antimony(III)sulfate catalyzed condensation reaction of indoles withcarbonyl compounds. Monatsh. Chem., 139: 111-115.
30. Ma, Z.C. and Z.H. Zhang, 2005. CuBr2-catalyzed synthesisof bis(indolyl) methanes. Synth. Commun. 35: 1997-2004.
31. Li, J.T., X.H. Zhang and Y.L. Song, 2010. Efficient synthesis of bis(indol-3-yl)methanes catalyzed by silicotungstic acid under ultrasound dirradiation. Int. J. Chem. Tech. Res. 2: 341-345.
32. Li, J.T., H.G. Dai, W.Z. Xu and T.S. Li, 2006. An efficient andpractical synthesis of bis(indolyl)methanes catalyzedby aminosulfonic acid under ultrasound. Ultrason Sonochem. 13: 24-27.
33. Bandgar, B.P., S.V. Bettigeri and N.S. Joshi, 2004. Hexamethylenetetraaminebromine catalyzed rapid and efficient synthesis of bis(indolyl)methanes. Monatsh.Chem. 135: 1265-1273.
34. Vaghei, R.G., H. Veisi, H. Keypour and A.A. Dehghani-Firouzabadi, 2010. A practical and efficient synthesis of bis(indolyl)methanesin water and synthesis of di-, tri-and tetra(bis-indolyl)methane sunder thermal conditions catalyzed by oxalic acid dehydrate. Mol. Divers. 14: 87-96.
35. Yadav, J.S., M.K. Gupta, R. Jain, N.N. Yadav and B.V.S. Reddy, 2010. A practical synthesis of bis(indolyl)methanes employing boric acid. Monatsh. Chem. 141: 1001-1004.
36. Kamal, A. and A.A. Qureshi, 1963. Syntheses of some substituted di-indolylmethanes in aqueous medium at room temperature. Tetrahedron. 19: 513-520.
37. Banerjee, B., S.K. Mandal and C.S. Roy, 2007. Efficient synthesis of bis(indolyl)methanes in aqueous medium catalyzed by molybdenyl acetylacetonate. Indian J. Chem. Sect B. 46: 669-673.
38. C.J. R. Nagarajan, M. Karthik and P.T. Perumal, 2004. Synthesis and characterization of bis(indolyl)methanes, tris(indolyl)methanes and new diindolylcarbazolylmethanes mediated by Zeokarb-225, a novel, recyclable, eco-benign heterogenous catalyst. Appl. Catal. A: General. 266: 1-10.
39. Ji, S.J., S.Y. Wang, Y. Zhang and T.P. Loh, 2004. Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions original research article. Tetrahedron. 60: 2051-2055.
40. Aliyan, H., R. Fazaeli, H.J. Naghash, A.R. Massah, A.R. Momeni and Z. Iravani, 2009. Bulk and supported tungstophosphoric acidas friendly, efficient, recyclable catalysts for the synthesis of bis-indolylmethanes under solvent-free conditions. Heteroatom Chemistry. 20: 325-331.
41. Zhang, Z., H. L. Yin and Y. M. Wang, 2005. An Efficient and Practical Process for the Synthesis of Bis(indolyl)methanes Catalyzed by Zirconium Tetrachloride. Synthesis. pp: 1949-1954.
42. Du, D.M., S.M. Meng, Y.M. Wang, J.B. Meng and X.Z. Zhou, 1995. Solid state reaction of aromatic ketones withheteroaromatics. Chin. J. Chem., 13: 520-524.
43. Zolfigol, M.A., P. Salehi, M. Shiri and Z. Tanbakouchian, 2007. A new catalytic method for the preparation of bis-indolyl and tris-indolyl methanes in aqueous media. Catal. Commun., 8: 173-178