Abstract
An operationally simple, efficient and environmentally benign synthetic method to bis(indolyl)methanes has been developed in good yields (80–96%) by electrophilic substitution reactions of indole with aldehydes or ketones in methanol in the presence of 5 mol% of poly (ethylene-glycol) (PEG) supported sulfonic acid with respect to indole under mild conditions. Recovery and recycling of the poly (ethylene-glycol)-supported catalyst were also described.
Graphical Abstract
A simple, facile and environmentally benign synthesis of bis(indolyl)methanes in good yields by reaction of indole with aldehydes or ketones in methanol using recyclable PEG-supported sulfonic acid as catalyst is described.
Similar content being viewed by others
References
Sundberg RJ (1996) The chemistry of indoles. Academic Press, New York, p 113
Osawa T, Namiki M (1983) Tetrahedron Lett 24:4719
Fahy E, Potts BCM, Faulkner DJ, Smith K (1991) J Nat Prod 54:564
Bell R, Carmeli S, Sar N (1994) J Nat Prod 57:1587
Bifulco G, Bruno I, Riccio R, Lavayre J, Bourdy G (1995) J Nat Prod 58:1254
Garbe TR, Kobayashi M, Shimizu N, Takesue N, Ozawa M, Yukawa H (2000) J Nat Prod 63:596
Gregorovich BV, Liang K, Clugston M, Macdonald S (1968) Can J Chem 46:3291
Roomi M, Macdonald S (1970) Can J Chem 48:139
Auria M (1991) Tetrahedron 47:9225
Chatterjee A, Manna S, Banerji J, Pascard C, Prangé T, Shoolery JN (1980) J Chem Soc Perkin Trans 1:553
Noland WE, Venkiteswaran MR, Richards CG (1961) J Org Chem 26:4241
Wang YM, Wen Z, Chen XM, Du DM, Matsuura T, Meng JB (1998) J Heterocycl Chem 35:313
Babu G, Sridhar N, Perumal PT (2000) Synth Commun 30:1609
Maiti AK, Bhattacharyya P (1997) J Chem Res (S) 424
Chen DP, Yu LB, Wang PG (1996) Tetrahedron Lett 37:4467
Nagarajan R, Perumal PT (2000) Tetrahedron 58:1229
Mi XL, Luo SZ, He JQ, Chen JP (2004) Tetrahedron Lett 45:4567
Wang L, Han J, Tian H, Sheng J, Fan Z, Tang X (2005) Synlett 337
Kobayashi S, Araki M, Yasuda M (1995) Tetrahedron Lett 36:5773
Yadav JS, Subba Reddy BV, Murthy CVSR, Kumar GM, Madan C (2001) Synthesis 783
Nagarajan R, Perumal PT (2002) Synth Commun 32:105
Ramesh C, Banerjee J, Pal R, Das B (2003) Adv Synth Catal 345:557
Bandgar BP, Shaikh KA (2003) Tetrahedron Lett 44:1959
Ji SJ, Wang SY, Zhang Y, Loh TP (2000) Tetrahedron 60:2051
Koshima H, Matsusaka W (2002) J Heterocycl Chem 39:1089
Yadav JS, Reddy BVS, Sunitha S (2003) Adv Synth Catal 345:349
Gu DG, Ji SJ, Jiang ZQ, Zhou MF, Loh TP (2005) Synlett 959
Deb ML, Bhuyan PJ (2006) Tetrahedron Lett 47:1441
Gravert DJ, Janda KD (1997) Chem Rev 97:489
Wentworth P, Janda KD (1999) Chem Commun 1917
Toy PH, Janda KD (2000) Acc Chem Res 33:546
Benaglia M, Puglisi A, Cozzi F (2003) Chem Rev 103:3401
Gladysz JA (2002) Chem Rev 102:3215
Dickerson TJ, Reed NN, Janda KD (2002) Chem Rev 102:3325
Sieber F, Wentworth P, Toker JD, Wentworth AD, Metz WA, Reed NN, Janda KD (1999) J Org Chem 64:5188
Behrendt JM, Bala K, Golding P, Hailes HC (2005) Tetrahedron Lett 46:643
Rees CW, Sabet CR (1965) J Chem Soc 680
Kamal A, Qureshi AA (1963) Tetrahedron 19:513
Acknowledgment
This work was financially supported by the National Natural Science Foundation of China (No. 20562005), NSF of Jiangxi Province (No. 0620021 and No. 2007GZW0185) and the Educational Committee of Jiangxi Province (GJJ08165).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Sheng, SR., Wang, QY., Ding, Y. et al. Synthesis of Bis(indolyl)methanes Using Recyclable PEG-Supported Sulfonic Acid as Catalyst. Catal Lett 128, 418–422 (2009). https://doi.org/10.1007/s10562-008-9767-z
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-008-9767-z