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http://dx.doi.org/10.5012/bkcs.2005.26.12.1962

Zirconium(IV) Chloride - Catalysed Reaction of Indoles: An Expeditious Synthesis of Bis(indolyl)methanes  

Nagawade, Rahul R. (Division of Medicinal Chemistry - New Drug Discovery, Wockhardt Research Centre)
Shinde, Devanand B. (Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University)
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Abstract
Zirconium(IV) chloride is found to be an efficient catalyst for the electrophilic addition reaction of indole with aldehydes/ketones to afford the corresponding bis(indolyl methanes in good yields. The remarkable features of this new procedure are high conversions, shorter reaction times, cleaner reaction profiles and simple experimental and work-up procedures.
Keywords
Zirconium(IV) chloride; Aldehydes; Ketones; Bis(indolyl)methanes; Indole;
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1 Kamal, A.; Qureshi, A. A. Tetrahedron 1963, 19, 513   DOI   ScienceOn
2 Babu, G.; Sridhar, N.; Perumal, P. T. Synth. Commun. 2000, 30, 1609   DOI   ScienceOn
3 Nagarajan, R.; Perumal, P. T. Tetrahedron 2002, 58, 1229   DOI   ScienceOn
4 Bandgar, B. P.; Shaikh, K. A. J. Chem. Res. Synop. 2004, 34
5 Zolfigol, M. A.; Salehi, P.; Shirl, M. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 2273   DOI   ScienceOn
6 Yadav, J. S.; Reddy, B. V. S.; Sunitha, S. Adv. Synth. Catal. 2003, 345, 349   DOI   ScienceOn
7 Mi, X. L.; Luo, S. Z.; He, J. Q.; Cheng, J. P. Tetrahedron Lett. 2004, 45, 4567   DOI   ScienceOn
8 Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. Adv. Synth. Catal. 2003, 345, 557   DOI   ScienceOn
9 Nagarajan, R.; Perumal, P. T. Synth. Commun. 2002, 32, 105   DOI   ScienceOn
10 Ramesh, C.; Ravindranath, N.; Das, B. J. Chem. Res. Synop. 2003, 72
11 Karthik, M.; Tripathi, A. K.; Gupta, N. M.; Palanichamy, M.; Murugesan, V. Catal. Commn. 2004, 5, 371   DOI   ScienceOn
12 Reddy, A. V.; Ravinder, R.; Reddy, V. L. N.; Goud, T. V.; Ravikanth, V.; Venkateseswarlu, Y. Synth. Commun. 2003, 33, 3687   DOI   ScienceOn
13 Chakrabarty, M.; Gosh, N.; Basak, R.; Harigaya, Y. Tetrahedron Lett. 2002, 43, 4075   DOI   ScienceOn
14 Penieres-Carrillo, G.; Garcia-Estrada, J. G.; Gutierrez-Ramirez, J. L.; Alvarez-Toledano, C. Green Chem. 2003, 5, 337
15 Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1999, 3, 319
16 Ji, S. J.; Zhou, M. F.; Gu, D. G.; Wang, S. Y.; Loh, T. P. Synlett 2003, 2077
17 Ji, S. J.; Zhou, M. F.; Gu, D. G.; Jiang, Z. Q.; Loh, T. P. Eur. J. Org. Chem. 2004, 1584
18 Lenarsic, R.; Kocevar, M.; Polanc, S. J. Org. Chem. 1999, 64, 2558   DOI   ScienceOn
19 Chary, K. P.; Mohan, G. H.; Iyengar, D. S. Chem. Lett. 1999, 12, 1339
20 Chary, K. P.; Ram, S. R.; Mohan, G. H.; Iyengar, D. S. Synlett 2000, 5, 683
21 Karimi, B.; Seradj, H. Synlett 2000, 6, 805
22 Reddy, V.; Mahesh, M.; Raju, P. V. K.; Ramesh, T.; Narayana Reddy, V. V. Tetrahedron Lett. 2002, 43, 2657   DOI   ScienceOn
23 Ji, S. J.; Wang, S. Y.; Zhang, Y.; Loh, T. P. Tetrahedron 2004, 60, 2051   DOI   ScienceOn
24 Bandgar, B. P.; Bettigeri, S. V.; Joshi, N. S. Monatsh. Chem. 2004, 135, 1265   DOI   ScienceOn
25 Sundberg, R. J. The Chemistry of Indoles; Academic: Newyork, 1996
26 Bell, R.; Carmeli, S.; Sar, N. J. Nat. Prod. 1994, 57, 1587   DOI   ScienceOn
27 Fahy, E.; Porn, B. C. M.; Faulkner, D. J.; Smith, K. J. Nat. Prod. 1991, 54, 564   DOI
28 Garbe, T. R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.; Yukawa, H. J. Nat. Prod. 2000, 63, 596   DOI   ScienceOn
29 Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1956
30 Xia, M.; Wang, S. B.; Yuan, W. B. Synth. Commun. 2004, 34, 3175   DOI   ScienceOn
31 Koshima, H.; Matsuaka, W. J. Heterocyclic Chem. 2002, 39, 1089   DOI   ScienceOn
32 Nagarajan, R.; Perumal, P. T. Chem. Lett. 2004, 33, 288   DOI   ScienceOn
33 Sharma, G. V. M.; Reddy, J. J.; Lakshmi, P. S.; Krishna, P. R. Tetrahedron Lett. 2004, 45, 7729   DOI   ScienceOn
34 Chen, D.; Yu, L.; Wang, P. G. Tetrahedron Lett. 1996, 37, 4467   DOI   ScienceOn
35 Yadav, J. S.; Reddy, B. V. S.; Murthy, V. S. R.; Kumar, G. M.; Madan, C. Synthesis 2001, 783
36 Wang, L. M.; Han, J. W.; Tian, H.; Sheng, J.; Fan, Z. Y.; Tang, X. P. Synlett 2005, 337
37 Feng, X. L.; Guan, C. J.; Zhao, C. X. Synth. Commun. 2004, 34, 487   DOI   ScienceOn
38 Ge, X.; Yannai, S.; Rennert, G.; Gruener, N.; Fares, F. A. Biochem. Biophys. Res. Commun. 1996, 228, 153   DOI   ScienceOn
39 Chakrabarty, M.; Basak, R.; Harigaya, Y. Heterocycles 2001, 55, 2431   DOI   ScienceOn