Zeolite Catalyzed Synthesis of bis(Indolyl) Methanes

Synthetic Communications

Volumn 33, Issue 21, 2003, Pages 3687-3694

  Reddy, A Vijender ^a   Ravinder, K ^a   Reddy, V L Niranjan ^a   Goud, T Venkateshwer ^a   Ravikanth, V ^a   Venkateswarlu, Y ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldehydes; bis(Indolyl) methanes; HY Zeolite; Indole

Indexed keywords

BIS(INDOLYL) METHANE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; ZEOLITE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0242268029     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120025177     Document Type: Article

References (25)

1. Carey, F.A.; Soundberg, R.J. Advanced Organic Chemistry; Part B, Plenum Press: New York.
2. Sundberg, R.J. The Chemistry of Indoles; Academic Press: New York, 1970.
3. Morris, S.A.; Anderson, R.J. Brominated bis (Indole) alkaloids from the marine sponge hexadella sp. Tetrahedron 1990, 46, 715.
4. Bifulco, G.; Bruno, I.; Riccio, R.; Lavayre, J.; Bourdy, G. Further brominated bis- and tris-indole alkaloid from the deep-water new Caledonain marine sponge Orina sp. J. Nat. Prod. 1995, 58, 1254.
5. Remers, W. Chem. Heterocycl. Compd. 1972, 25, 1.
6. 1. Can. J. Chem. 1970, 48, 139;
7. (b) Gregorovich, B.; Liang, K.; Clugston, D.; MacDonald, S. Reductive C-alkylation. Can. J. Chem. 1968, 46, 3291.
8. (a) Woland, W.; Venkiteswaren, M.; Richards, C. Cyclizative condensations. 1,2-methylindole with acetone and methyl ketone. J. Org. Chem. 1961, 26, 4241;
9. (b) Banerji, J.; Chatterjee, A.; Manna, S.; Pascard, C.; Prange, T.; Shoolery, Lewis acid induced electrophilic substitution of indole: part 3. J. Heterocycles 1981, 15, 325.
10. (a) Chatterjee, A.; Manna, S.; Benerji, J.; Pascard, C.; Prange, T.; Shoolery, J. Lewis-acid-induced electrophilic substitution in indoles with acetone. part 2. J. Chem. Soc., Perkin Trans-1 1980, 553;
11. (b) Babu, G.; Sridher, N.; Perumal, P.T. A convenient method of synthesis of bis indolyl methanes: indium trichloride catalyzed reactions of indole with aldehydes and schiff's bases. Synth. Commun. 2000, 30, 1609.
12. Yadav, J.S.; Reddy, B.V.S.; Murthy, Ch. V.S.R.; Kumar, G.M.; Madan, Ch. Lithium perchlorate catalyzed reactions of indoles: an expeditious synthesis of bis (indolyl) methanes. Synthesis 2001, 783.
13. Chen, D.; Yu, L.; Wang, P.G. Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones. Tetrahedron Lett. 1996, 37, 4467.
14. Kobayashi, S.; Araki, M.; Yasuda, M. One-pot synthesis of β-amino esters from aldehydes using lanthanide triflate as a catalyst. Tetrahedron Lett. 1995, 36, 5773.
15. (a) Ramesh, P.; Reddy, V.L.N.; Venugopal, D.; Subrahamanyam, M.; Venkateswarlu, Y. Zeolite catalyzed ring opening of epoxides to acetylated diols with acetic anhydride. Synth. Commun. 2001, 31, 2599;
16. (b) Ballini, R.; Bosica, G.; Carloni, S.; Ciaralli, L.; Maggi, R.; Sartori, G. Selective deprotection strategies to N- (α -methylbenzyl)-β-amino esters and derived β-lactums. Tetrahedron Lett. 1998, 39, 6049;
17. (c) Lakshmi Kantham, M.; Choudary, B.M.; Bharathi, B. Ring opening of oxiranes catalyzed by Mn-Salen immobilized mesoporous materials. Synth. Commun. 1999, 29, 1121.
18. Balogh, M.; Laszlo, P. In Organic Chemistry using Clays; Spinger-Verlag, Ed.; Berlin, 1993 and references cited therein.
19. 14. (a) Holderich, W.; Hesse, M.; Neumann, F. Zeolites: catalysts for organic syntheses. Angew. Chem. 1988, 27, 226;
20. (b) Ramamurthy, V.; Corbin, D.R.; Johnston, L.J. A study of Norrish type II reactions of aryl alkyl ketones included within zeolites. J. Am. Chem. Soc. 1992, 114, 3870;
21. (c) Oitchumani, K.; Warrier, M.; Ramamurthy, V. Remarkable product selectivity during photo-fries and photo-claisen rearrangements within zeolites. J. Am. Chem. Soc. 1996, 118, 9428;
22. (d) Venuto, P.B.; Landy, P.B. Advances in Catalysis 1968, 18, 259.
23. (a) Martens, J.A.; Souverijns, W.; Verrelst, W.; Parton, R.; Froment, U.F.; Jacobs, P.A. Isomerization of hydrocarbon chains on external surfaces of zeolite crystals. Angew. Chem. Int. Ed. 1995, 34, 2528;
24. 2,6] undec-32 (6)-en-7-one from the corresponding spiro lactams using zeolite. Use of the zeolite as micro reaction vessel. J. Chem. Soc. Chem. Commun. 1992, 1624;
25. (c) Sreekumar, R.; Padmakumar, R.; Rugmini, P. Conversion of alkenes and alcohols to azides over-zeolite supported sodijm azides. J. Chem. Soc. Chem. Comm. 1997, 1133.