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A simple and efficient route for the synthesis of di and tri(bis(indolyl) methanes) as new triarylmethanes

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Abstract

Preparation of di and tri(bis(indolyl) methanes) from di and trialdehydes and indoles in the presence of silica sulfuric acid was described. Reactions proceeded in good to excellent yields in acetonitrile as solvent at room temperature.

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References

  1. Glasby, JS (eds) (1975) Encyclopedia of the alkaloids. Plenum Press, New York

    Google Scholar 

  2. Sundberg RJ (1996) The chemistry of indoles. Academic Press, New York

    Google Scholar 

  3. Ramesh C, Banerjee J, Pal R, Das B (2003) Silica supported sodium hydrogen sulfate and amberlyst-15: Two efficient heterogeneous catalysts for facile synthesis of bis-and tris(1H-indol-3-yl)methanes from indoles and carbonyl compounds. Adv Synth Catal 345: 557–559. doi:10.1002/adsc.200303022

    Article  CAS  Google Scholar 

  4. Yadav JS, Subba Reddy BV, Murthy ChVSR, Mahesh Kumar G, Madan Ch (2001) Lithium perchlorate catalyzed reactions of indoles: an expeditious synthesis of bis(indolyl)methanes. Synthesis 5: 783–787. doi:10.1055/s-2001-12777

    Article  Google Scholar 

  5. Mi X, Luo S, Hea J, Chenga JP (2004) Dy(OTf)3 in ionic liquid: an efficient catalytic system for reactions of indole with aldehydes/ketones or imines. Tetrahedron Lett 45: 4567–4570. doi:10.1016/j.tetlet.2004.04.039

    Article  CAS  Google Scholar 

  6. Sato S, Sato T (2005) A mild and environmentally friendly scandium(III) trifluoromethanesulfonate-catalyzed synthesis of bis(3′-indolyl)alkanes and bis(3′-indolyl)-1-deoxyalditols. Carbohydr Res 340: 2251–2255. doi:10.1016/j.carres.2005.07.019

    Article  PubMed  CAS  Google Scholar 

  7. Mo LP, Ma ZC, Zhang ZH (2005) CuBr2-catalyzed synthesis of bis(indolyl)methanes. Synth Commun 35: 1997–2004. doi:10.1081/SCC-200066653

    Article  CAS  Google Scholar 

  8. Zhang ZH, Yin L, Wang YM (2005) An efficient and practical process for the synthesis of bis(indolyl)methanes catalyzed by zirconium tetrachloride. Synthesis 12: 1949–1954

    Google Scholar 

  9. Nair V, Abhilash KG, Vidya N (2005) Practical synthesis of triaryl- and triheteroarylmethanes by reaction of aldehydes and activated arenes promoted by gold(III) chloride. Org Lett 7: 5857–5859. doi:10.1021/ol052423h

    Article  PubMed  CAS  Google Scholar 

  10. Firouzabadi H, Iranpoor N, Jafari AA, (2006) Aluminumdodecatungstophosphate (AlPW12O40), a versatile and a highly water tolerant green Lewis acid catalyzes efficient preparation of indole derivatives. J Mol Catal A Chem 244:8–172 and references here sited

    Google Scholar 

  11. Zolfigol MA (2001) Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions. Tetrahedron 57: 9509–9511. doi:10.1016/S0040-4020(01)00960-7

    Article  CAS  Google Scholar 

  12. Salehi P, Zolfigol MA, Shirini F, Baghbanzadeh M (2006) Silica sulfuric acid and silica chloride as efficient reagents for organic reactions. Curr Org Chem 10: 2171–2189. doi:10.2174/138527206778742650

    Article  CAS  Google Scholar 

  13. Zolfigol MA, Habibi D, Mirjalili BF, Bamoniri A (2003) The use of Nafion-H®/NaNO2 as an efficient procedure for the chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions. Tetrahedron Lett 44: 3345–3349. doi:10.1016/S0040-4039(03)00578-1

    Article  CAS  Google Scholar 

  14. Zolfigol MA, Madrakian T, Ghaemi E, Afkhami A, Azizian S, Afshar S (2002) Synthesis of morpholinated and 8-hydroxyquinolinated silica gel and their application to water softening. Green Chem 4: 611–614. doi:10.1039/b208526g

    Article  CAS  Google Scholar 

  15. Bamoniri A, Zolfigol MA, Mohammadpoor-Baltork I, Mirjalili BF (2006) The use of silica sulfuric acid as an efficient catalyst for deprotection of trimethylsilyl ethers to the corresponding alcohols under mild and heterogeneous conditions. J Iran Chem Soc 3: 85–88

    CAS  Google Scholar 

  16. Zolfigol MA, Bamoniri A (2002) Silica sulfuric acid/NaNO2 as a novel heterogeneous system for the chemoselective N-nitrosation of secondary amines under mild conditions. Synlett 1621–1624. doi:10.1055/s-2002-34230

  17. Zolfigol MA, Mohammadpoor-Baltork I, Mirjalili BF, Bamoniri A (2003) Silica sulfuric acid: an efficient catalyst for the direct conversion of primary and secondary trimethylsilyl ethers to their corresponding ethers under mild and heterogeneous conditions. Synlett 1877–1879. doi:10.1055/s-2003-41469

  18. Zolfigol MA, Mohammadpoor-Baltork I, Khazaei A, Shiri M, Tanbakouchian Z (2006) SiO2/N2O4 and Fe(NO3)3·9H2O/H3PMo12O40 ·xH2O systems as powerful oxidants for removal of cyclic dioxalanes and dithianes. Lett Org Chem 3: 305–308. doi:10.2174/157017806776114676

    Article  CAS  Google Scholar 

  19. Zolfigol MA, Salehi P, Shiri M (2004) An efficient procedure for the preparation of mono, and di-bisindolyl methane’s catalyzed by molibdatophosphoric acid. Phosphorus Sulfur Silicon 178: 2273–2277. doi:10.1080/10426500490484904

    Article  Google Scholar 

  20. Zolfigol MA, Salehi P, Shiri M, Tanbakouchian Z (2007) A new catalytic method for the preparation of bis-indolyl and tris-indolyl methanes in aqueous media. Catal Commun 8: 173–178. doi:10.1016/j.catcom.2006.06.012

    Article  CAS  Google Scholar 

  21. Niknam K, Zolfigol MA, Sadabadi T, Nejati A (2006) Preparation of indolylmethanes catalyzed by metal hydrogen sulfates. J Iran Chem Soc 3: 318–322

    CAS  Google Scholar 

  22. Tahmassebi DC, Sasaki T (1994) Synthesis of a new trialdehyde template for molecular imprinting. J Org Chem 59: 679–681. doi:10.1021/jo00082a034

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Mohammad Ali Zolfigol, Morteza Shiri, Azam Sayadi, Abbas Abdoli, Hassan Keypour, Majid Rezaeivala & Eskandar Kolvari

  2. Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, 1983963113, Iran

    Peyman Salehi

  3. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75168, Iran

    Khodabakhsh Niknam

Authors
  1. Mohammad Ali Zolfigol
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  2. Peyman Salehi
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  3. Morteza Shiri
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  4. Azam Sayadi
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  5. Abbas Abdoli
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  6. Hassan Keypour
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  7. Majid Rezaeivala
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  8. Khodabakhsh Niknam
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  9. Eskandar Kolvari
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Correspondence to Mohammad Ali Zolfigol.

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Zolfigol, M.A., Salehi, P., Shiri, M. et al. A simple and efficient route for the synthesis of di and tri(bis(indolyl) methanes) as new triarylmethanes. Mol Divers 12, 203–207 (2008). https://doi.org/10.1007/s11030-008-9091-y

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  • DOI: https://doi.org/10.1007/s11030-008-9091-y

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