Abstract
1-benzyl-3-methyl imidazolium hydrogen sulphate [bnmim][HSO4] was found to be an effective catalyst for the condensation reaction of indoles and derivatives with benzaldehydes in microwave irradiation with lower reaction time and higher yields to give bis(indolyl) methanes.
Similar content being viewed by others
References
T. Welton, Chem. Rev. 99, 2071 (1999)
P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed. 39, 3772 (2000)
R. Sheldon, Chem. Commun. 2399 (2001)
C.O. Kappe, Tetrahedron 49, 6937 (1993) and references cited therein
J. G. Huddleston, A. E. Visser, W. M. Reichert, H. D. Willauer, G. A. Broker and R. D. Rogers, Green Chem. 3, 156 (2001)
S. Lee, J. H. Park, J. Kang and J. K. Lee, Chem. Commun. 1698 (2001)
S. Csihony, C. Fischmeister, C. Bruneau, I. T. Horvath and P. H. Dixneuf, New J. Chem. 11, 1667 (2002)
(a) T. Fischer, A. Sethi, T. Welton, J. Woolf, Tetrahedron Lett. 40, 793 (1999); (b) Z. Baan, Z. Finta, G. Keglevich and I. Hermecz, Tetrahedron Lett. 46, 6203 (2005)
A. Agarwal, N. L. Lancaster, A. R. Sethi and T. Welton, Green Chem. 5, 517 (2002)
R.S. Varma and V.V. Namboodiri, Pure Appl. Chem. 73, 1309 (2001)
J. Fraga-Dubreuil, J. K. Bourahla, M. Rahmouni, J. P. Bazureau and J. Hamelin, Catal. Commun. 3, 185 (2002)
M.K. Potdar, S.S. Mohile and M.M. Salunkhe, Tetrahedron Lett. 42, 9285 (2001)
(a) T. Osawa and M. Namiki, Tetrahedron Lett. 24, 4719 (1983); (b) J.K. Porter, C.W. Bacon, J.D. Robbin, D.S. Himmelsbach and H.C. Higman, J Agric Food Chem. 25, 88 (1977); (c) T.R. Garbe, M. Kobayashi, N. Shimizu, N. Takesue, M. Ozawa and H. Yukawa, J Nat Prod. 63, 596 (2000)
(a) G.W. Gribble, In comprehensive Heterocyclic Chemistry, 2nd ed. (Pergamon Pres: New York, 1996) 202; (b) V. Snieckus, In The Alkaloids (Academic Press: New York, 1998) 11
C. Hong, G.L. Firestone, L.F. Bjeldanes, Biochem. Pharmaco 63, 1085 (2002)
X. Ge, S. Yannai, G. Rennert, N. Gruener and F. A. Fares, Biochem. Biophys. Res. Commun. 228, 153 (1996)
(a) C. Lin, J. Hsu, M.N.V. Sastry, H. Fang, Z. Tu, J. Liu and Y. Ching-Fa, Tetrahedron, 61, 11751 (2005); (b) G. Bartoli, M. Bartolacci, M. Bosco, G. Foglia, A. Giuliani, E. Mareantoni, L. Sambri and E. Torregiani, J. Org. Chem. 68, 4594 (2003)
P. Anastas and J. C. Warner, Green chemistry, theory and practice (Oxford, UK, 1998)
L. M. Wang, J. W. Han, H. Tian, J. Sheng, Z. Y. Fan and X. P. Tang, Synlett 337 (2005)
G. V. M. Sharma, J. J. Reddy, P. S. Lakshmi and P. R. Krishna, Tetrahedron Lett. 45, 7729 (2004)
B. P. Bandgar, S. V. Bettigeri and N. S. Joshi, Monatsh. Chem. 135, 1265 (2004)
X. L. Feng, C. J. Guan and C. X. Zhao, Synth. Commun. 34, 487 (2004)
(a) S. J. Ji, M. F. Zhou, D. G. Gu, S. Y. Wang and T. P. Loh, Synlett 2077 (2003); (b) S. J. Ji, M. F. Zhou, D. G. Gu, Z. Q. Jiang and T. P. Loh, Eur. J. Org. Chem. 1584 (2004)
R. R. Nagawade and D. B. Shinde, Acta Chim. Slov. 53, 210 (2006)
R. R. Nagawade, D. B. Shinde, Bull. Korean Chem. Soc. 26, 12 (2005)
A. Srinivasa, P.P. Varma, V. Hulikal and K. M. Mahadevan, Monatsh. Chem., 39, 111 (2008)
A. Khallafi-Nezhad et. al., Synthesis 617 (2008)
H. Firouzabadi, N. Iranpoor, M. Jafarpour, A. Ghaderi, J. Mol. Catal. A: Chem., 253, 249 (2006)
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Sadaphal, S.A., Shelke, K.F., Sonar, S.S. et al. Ionic liquid promoted synthesis of bis(indolyl) methanes. cent.eur.j.chem. 6, 622–626 (2008). https://doi.org/10.2478/s11532-008-0069-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11532-008-0069-5