RuCl3·3H2O catalyzed reactions: Facile synthesis of bis(indolyl)methanes under mild conditions

Molecules

Volumn 16, Issue 5, 2011, Pages 3855-3868

  Qu, Hong En ^a   Xiao, Chen ^a   Wang, Ning ^a   Yu, Kai Hui ^a   Hu, Qiao Sheng ^a   Liu, Liang Xian ^a  

^a GANNAN NORMAL UNIVERSITY   (China)

Author keywords

Aldehyde; Bis(indolyl)methane; Indole; RuCl3 3H2O

Indexed keywords

DRUG DERIVATIVE; METHANE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CATALYSIS; METHANE; MOLECULAR STRUCTURE; RUTHENIUM;

EID: 79957586814     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16053855     Document Type: Article

References (30)

1. Lounasmaa, M.; Tolvanen, A. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat. Prod. Rep. 2000, 17, 175-191. (Pubitemid 30218021)
2. Hibino, S.; Chozi, T. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat. Prod. Rep. 2001, 18, 66-87. (Pubitemid 32160984)
3. Porter, J.K.; Bacon, C.W.; Robins, J.D.; Himmelsbach, D.S.; Higman, H.C. Indole alkaloids from Balansia epichloë. J. Agric. Food Chem. 1977, 25, 88-93.
4. Osawa, T.; Namiki, M. Structure elucidation of streptindole, a novel genotoxic metabolite isolated from intestinal bacteria. Tetrahedron Lett. 1983, 24, 4719-4722.
5. Fahy, E.; Potts, B.C.M.; Faulkner, D.J.; Smith, K. 6-Bromotryptamine derivatives from the gulf of california tunicate didemnum candidum. J. Nat. Prod. 1991, 54, 564-569.
6. Bell, R.; Carmeli, S.; Sar, N.; Vibrindole, A. A metabolite of the marine bacterium, vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish ostracion cubicus. J. Nat. Prod. 1994, 57, 1587-1590.
7. Garbe, T.R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.; Yukawa, H. Indolyl carboxylic acids by condensation of indoles with α-keto acids. J. Nat. Prod. 2000, 63, 596-598. (Pubitemid 30395510)
8. Faulkner, D.J. Marine natural products. Nat. Prod. Rep. 2001, 18, 1-49. (Pubitemid 32160982)
9. Morris, S.A.; Anderson, R.J. Brominated bis(indole) alkaloids from the marine sponge hexadella SP. Tetrahedron 1990, 46, 715-720. (Pubitemid 20128139)
10. Bifulco, G.; Bruno, I.; Riccio, R.; Lavayre, J.; Bourdy, G. Further brominated bis- and tris-indole alkaloids from the deep-water new caledonian marine sponge orina sp. J. Nat. Prod. 1995, 58, 1254-1260.
11. Ji, S.-J.; Zhou, M.-F.; Gu, D.-J.; Jiang, Z.-Q.; Loh, T.-P. Efficient FeIII-catalyzed synthesis of bis(indolyl)methanes in ionic liquids. Eur. J. Org. Chem. 2004, 1584-1587.
12. Reddy, A.V.; Ravinder, K.; Reddy, V.L.N.; Goud, T.V.; Ravikanth, V.; Venkateswarlu, Y. Zeolite catalyzed synthesis of bis(indolyl) methanes. Synth. Commun. 2003, 33, 3687-3694. (Pubitemid 37351854)
13. Mahadevan, A.; Sard, H.; Gonzalez, M.; McKew, J.C. A general method for C3 reductive alkylation of indoles. Tetrahedron Lett. 2003, 44, 4589-4591. (Pubitemid 36588638)
14. Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. Silica supported sodium hydrogen sulfate and amberlyst-15: Two efficient heterogeneous catalyst for facile synthesis of bis- and tris(1H-indol-3-yl) methanes from indoles and carbonyl compounds. Adv. Synth. Catal. 2003, 345, 557-559. (Pubitemid 37386895)
15. 3 catalyzed reactions: Synthesis of 3-acetyl indoles, bis-indolylmethane and indolylquinoline derivatives. Tetrahedron 2002, 58, 1229-1232. (Pubitemid 34112600)
16. Giannini, G.; Marzi, M.; Marzo, M.D.; Battistuzzi, G.; Pezzi, R.; Brunetti, T.; Cabri, W.; Vesci, L.; Pisano, C. Exploring bis-(indolyl)methane moiety as an alternative and innovative CAP group in the design of histone deacetylase (HDAC) inhibitors. Bioorg. Med. Chem. Lett. 2009, 19, 2840-2843.
17. Giannini, G.; Marzi, M.; Moretti, G.P.; Penco, S.; Tinti, M.O.; Pesci, S.; Lazzaro, F.; Angelis, F.D. Synthesis of cycloalkanoindoles by an unusual DAST-triggered rearrangement reaction. Eur. J. Org. Chem. 2004, 2004, 2411-2420.
18. Chen, D.-P.; Yu, L.-B.; Wang, P.-G. Lewis acid-catalyzed reactions in protic media. Lanthanidecatalyzed reactions of indoles with aldehydes or ketones. Tetrahedron Lett. 1996, 37, 4467-4470.
19. 2O: A new and efficient recyclable medium for the synthesis of bis(indolyl)-methanes. Tetrahedron Lett. 2009, 50, 6060-6063.
20. Bartoli, G.; Bosco, M.; Foglia, G.; Giuliani, A.; Marcantoni, E.; Sambri, L. Solvent-free indoles addition to carbonyl compounds promoted by CeCl 7 HO-NaI-SiO: An efficient method for the synthesis of streptindole. Synthesis 2004, 6, 895-900. (Pubitemid 38594672)
21. Ji, S.-J.; Wang, S.-Y.; Zhang, Y.; Loh, T.-P. Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions. Tetrahedron 2004, 60, 2051-2055. (Pubitemid 38201586)
22. Bandgar, B.P.; Shaikh, K.A. Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions. Tetrahedron Lett. 2003, 44, 1959-1961. (Pubitemid 36183442)
23. Chakrabarty, M.; Ghosh, N.; Basak, R.; Harigaya, Y. Dry reaction of indoles with carbonyl compounds on montmorillonite K10 clay: A mild, expedient synthesis of diindolylalkanes and vibrindole A. Tetrahedron Lett. 2002, 43, 4075-4078. (Pubitemid 34603231)
24. Li, J.; Zhou, M.; Li, B.-G.; Zhang, G.-L. Synthesis of triindolylmethanes catalyzed by zeolites. Synth. Commun. 2004, 34, 275-280. (Pubitemid 38250452)
25. Chakrabarty, M.; Sarkar, S. Novel clay-mediated, tandem addition-elimination-(Michael) addition reactions of indoles with 3-formylindole: An eco-friendly route to symmetrical and unsymmetrical triindolylmethanes. Tetrahedron Lett. 2002, 43, 1351-1353. (Pubitemid 34127900)
26. Deb, M.L.; Bhuyan, P.J. An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature. Tetrahedron Lett. 2006, 47, 1441-1443. (Pubitemid 43151159)
27. Nair, V.; Abhilash, K.G.; Vidya, N. Practical synthesis of triaryl- and triheteroarylmethanes by reaction of aldehydes and activated arenes promoted by gold(III) chloride. Org. Lett. 2005, 7, 5857-5859. (Pubitemid 43052870)
28. Swain, C.G.; Lupton, E.C., Jr. Field and resonance components of substituent effects. J. Am. Chem. Soc. 1968, 90, 4328-4337.
29. Penieres-Carrillo, G.; Garcia-Estrada, J.G.; Gutierrez-Ramirez J.L.; Alvarez-Tolendano, C. Infrared-assisted eco-friendly selective synthesis of diindolylmethanes. Green Chem. 2003, 5, 337-339.
30. Yadav, J.S.; Reddy, B.V.S.; Murthy, C.V.S.R.; Kumar, G.M.; Madan, C. Lithium perchlorate catalyzed reactions of indoles: An expeditious synthesis of bis(indolyl) methanes. Synthesis 2001, 5, 783-787. (Pubitemid 32378560)