Efficient and Eco-Friendly Process for the Synthesis of Bis(1H-indol-3-yl)methanes using Ionic Liquids

Advanced Synthesis and Catalysis

Volumn 345, Issue 3, 2003, Pages 349-352

  Yadav, J S ^a   Reddy, B V S ^a   Sunitha, S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldehydes; Bis indolylmethanes; Ionic liquids; Ketones

Indexed keywords

CARBONYL DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; LIQUID; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; RECYCLING; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0242607159     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200390038     Document Type: Article

References (26)

1. a) P. Ehrlich, Medicin Woche 1901, 151;
2. b) L. Morgan, R. Schunior, J. Org. Chem. 1962, 27, 3696;
3. c) D. J. Dolphin, Heterocycl. Chem. 1979, 7, 275.
4. W. Remers, Chem. Heterocycl. Compounds 1972, 25, 1.
5. a) W. E. Noland, M. R. Venkiteswaran, C. G. Richards, J. Org. Chem. 1961, 26, 4241;
6. b) J. Banerji, A. Chatterjee, S. Manna, C. Pascard, T. Prange, J. Shoolery, Heterocycles 1981, 15, 325.
7. a) A. Chatterjee, S. Manna, J. Benerji, T. Prange, J. Shoolery, J. Chem. Soc. Perkin Trans.I 1980, 553;
8. b) G. Babu, N. Sridhar, P. T. Perumal, Synth. Commun. 2000, 30, 1609.
9. a) M. Roomi, S. MacDonald, Can. J. Chem. 1970, 48, 139;
10. b) B. Gregorovich, K. Liang, D. Clugston, S. MacDonald, Can. J. Chem. 1968, 46, 3291.
11. a) D. Chen, L. Yu, P. G. Wang, Tetrahedron Lett. 1996, 37, 4467;
12. b) S. Kobayashi, M. Araki, M. Yasuda, Tetrahedron Lett. 1995, 36, 5773;
13. c) M. Johannsen, Chem. Commun. 1999, 2223;
14. d) W. Z. Luang, N. Gathergood, R. G. Hazel, K. A. Joergenson, J. Org. Chem. 2001, 66, 1009.
15. a) Recent reviews on ionic liquids: T. Welton, Chem. Rev. 1999, 99, 2071;
16. b) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772;
17. c) Catalytic reactions in ionic liquids: R. Sheldon, Chem. Commun. 2001, 2399.
18. Ionic liquids have already been described as catalysts: a) C. Wheeler, K. N. West, C. L. Liotta, C. A. Eckert, Chem. Commun. 2001, 887; b) J. Peng, Y. Deng, Tetrahedron Lett. 2001, 42, 5917; Brønsted acidic ionic liquids as dual solvent and catalysts: A. C. Cole, J. L. Jensen, I. Ntai, K. L. T. Tran, K. J. Weaver, D. C. Forbes, J. H. Davis Jr., J. Am. Chem. Soc. 2002, 124, 5962.
19. Ionic liquids have already been described as catalysts: a) C. Wheeler, K. N. West, C. L. Liotta, C. A. Eckert, Chem. Commun. 2001, 887; b) J. Peng, Y. Deng, Tetrahedron Lett. 2001, 42, 5917; Brønsted acidic ionic liquids as dual solvent and catalysts: A. C. Cole, J. L. Jensen, I. Ntai, K. L. T. Tran, K. J. Weaver, D. C. Forbes, J. H. Davis Jr., J. Am. Chem. Soc. 2002, 124, 5962.
20. Ionic liquids have already been described as catalysts: a) C. Wheeler, K. N. West, C. L. Liotta, C. A. Eckert, Chem. Commun. 2001, 887; b) J. Peng, Y. Deng, Tetrahedron Lett. 2001, 42, 5917; c) Brønsted acidic ionic liquids as dual solvent and catalysts: A. C. Cole, J. L. Jensen, I. Ntai, K. L. T. Tran, K. J. Weaver, D. C. Forbes, J. H. Davis Jr., J. Am. Chem. Soc. 2002, 124, 5962.
21. [9] Preparation of ionic liquids: a) S. Park, R. J. Kazlauskas, J. Org. Chem. 2001, 66, 8395; b) P. Bonhote, A. P. Dias, N. Papageorgiou, K. Kalyanasundaram, M. Gratzel, Inorg. Chem. 1996, 35, 1168.
22. Preparation of ionic liquids: a) S. Park, R. J. Kazlauskas, J. Org. Chem. 2001, 66, 8395; b) P. Bonhote, A. P. Dias, N. Papageorgiou, K. Kalyanasundaram, M. Gratzel, Inorg. Chem. 1996, 35, 1168.
23. [10] Friedel-Crafts alkylation reactions in ionic liquids: a) P. Formentin, H. Garcia, Catal. Lett. 2002, 78, 155; b) C. D. E. Jong, W. K. J. Shim, E. J. Roo, J. M. Choi, Chem. Commun. 2000, 1695.
24. Friedel-Crafts alkylation reactions in ionic liquids: a) P. Formentin, H. Garcia, Catal. Lett. 2002, 78, 155; b) C. D. E. Jong, W. K. J. Shim, E. J. Roo, J. M. Choi, Chem. Commun. 2000, 1695.
25. a) H. Chalaye-Mauger, J. N. Denis, M. T. Averbuch-Pouchot, Y. Vallee, Tetrahedron 2000, 56, 791;
26. b) J. S. Yadav, B. V. S. Reddy, C. V. S. R. Murthy, G. M. Kumar, C. Madan, Synthesis 2001, 783.