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

Molecular Diversity

Volumn 12, Issue 3-4, 2008, Pages 203-207

  Zolfigol, Mohammad Ali ^a   Salehi, Peyman ^b   Shiri, Morteza ^a   Sayadi, Azam ^a   Abdoli, Abbas ^a   Keypour, Hassan ^a   Rezaeivala, Majid ^a   Niknam, Khodabakhsh ^c   Kolvari, Eskandar ^a  

^a BU ALI SINA UNIVERSITY   (Iran)

^b SHAHID BEHESHTI UNIVERSITY   (Iran)

^c PERSIAN GULF UNIVERSITY   (Iran)

Author keywords

Bisindolyl methanes; Dialdehydes; Indoles; Silica sulfuric acid; Trialdehydes

Indexed keywords

ACETONITRILE; ALDEHYDE; DIALDEHYDE; INDOLE DERIVATIVE; METHANE; SULFURIC ACID; TRIALDEHYDE; TRIARYLMETHANE; UNCLASSIFIED DRUG; SILICON DIOXIDE;

ARTICLE; CHEMICAL STRUCTURE; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS; CHEMISTRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TECHNIQUE;

ALDEHYDES; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; METHODS; MOLECULAR STRUCTURE; SILICON DIOXIDE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SULFURIC ACIDS;

EID: 60549115295     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-008-9091-y     Document Type: Article

References (22)

1. Glasby, JS (eds) (1975) Encyclopedia of the alkaloids. Plenum Press, New York
2. Sundberg RJ (1996) The chemistry of indoles. Academic Press, New York
3. C Ramesh J Banerjee R Pal B Das 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 10.1002/adsc.200303022
4. JS Yadav BV Subba Reddy ChVSR Murthy G Mahesh Kumar Ch Madan 2001 Lithium perchlorate catalyzed reactions of indoles: an expeditious synthesis of bis(indolyl)methanes Synthesis 5 783 787 10.1055/s-2001-12777
5. 3 in ionic liquid: an efficient catalytic system for reactions of indole with aldehydes/ketones or imines Tetrahedron Lett 45 4567 4570 10.1016/j.tetlet.2004.04.039
6. S Sato T Sato 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 10.1016/j.carres. 2005.07.019
7. 2-catalyzed synthesis of bis(indolyl)methanes Synth Commun 35 1997 2004 10.1081/SCC-200066653
8. ZH Zhang L Yin YM Wang 2005 An efficient and practical process for the synthesis of bis(indolyl)methanes catalyzed by zirconium tetrachloride Synthesis 12 1949 1954
9. V Nair KG Abhilash N Vidya 2005 Practical synthesis of triaryl- and triheteroarylmethanes by reaction of aldehydes and activated arenes promoted by gold(III) chloride Org Lett 7 5857 5859 10.1021/ol052423h
10. 40), 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
11. 2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions Tetrahedron 57 9509 9511 10.1016/S0040-4020(01)00960-7
12. P Salehi MA Zolfigol F Shirini M Baghbanzadeh 2006 Silica sulfuric acid and silica chloride as efficient reagents for organic reactions Curr Org Chem 10 2171 2189 10.2174/138527206778742650
13. 2 as an efficient procedure for the chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions Tetrahedron Lett 44 3345 3349 10.1016/S0040-4039(03)00578-1
14. MA Zolfigol T Madrakian E Ghaemi A Afkhami S Azizian S Afshar 2002 Synthesis of morpholinated and 8-hydroxyquinolinated silica gel and their application to water softening Green Chem 4 611 614 10.1039/b208526g
15. A Bamoniri MA Zolfigol I Mohammadpoor-Baltork BF Mirjalili 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
16. 2 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. 2O systems as powerful oxidants for removal of cyclic dioxalanes and dithianes Lett Org Chem 3 305 308 10.2174/ 157017806776114676
19. MA Zolfigol P Salehi M Shiri 2004 An efficient procedure for the preparation of mono, and di-bisindolyl methane's catalyzed by molibdatophosphoric acid Phosphorus Sulfur Silicon 178 2273 2277 10.1080/10426500490484904
20. MA Zolfigol P Salehi M Shiri Z Tanbakouchian 2007 A new catalytic method for the preparation of bis-indolyl and tris-indolyl methanes in aqueous media Catal Commun 8 173 178 10.1016/j.catcom.2006.06.012
21. K Niknam MA Zolfigol T Sadabadi A Nejati 2006 Preparation of indolylmethanes catalyzed by metal hydrogen sulfates J Iran Chem Soc 3 318 322
22. DC Tahmassebi T Sasaki 1994 Synthesis of a new trialdehyde template for molecular imprinting J Org Chem 59 679 681 10.1021/jo00082a034