Novel multiple-acidic ionic liquids: Green and efficient catalysts for the synthesis of bis-indolylmethanes under solvent-free conditions

Anguo Ying; Zhifeng Li; Yuxiang Ni; Songlin Xu; Hailiang Hou; Huanan Hu

Journal of Industrial and Engineering Chemistry, Vol.24, 127-131, April, 2015

DOI10.1016/j.jiec.2014.09.019 Export Citation

Novel multiple-acidic ionic liquids: Green and efficient catalysts for the synthesis of bis-indolylmethanes under solvent-free conditions

Anguo Ying^†, Zhifeng Li¹, Yuxiang Ni¹, Songlin Xu¹, Hailiang Hou¹, and Huanan Hu

School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, People’s Republic of China
¹School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People’s Republic of China

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Four novel multiple-acidic ionic liquids based on triethanolamine (TEA) were prepared and used as efficient catalysts to synthesize bis-indolylmethanes at room temperature without any organic solvent. [TEOA][HSO4] showed the best catalytic performance. The optimal amount of catalyst was 10 mol%. Various aldehydes/ketones reacted with indole/substituted indole smoothly and afforded to corresponding products in 70?99% yields within minutes. Additionally, the ionic liquid could be reused up to five times with only a slight decrease in catalytic activity. Finally, a possible reaction mechanism was given. Techniques of acidity test and NMR were introduced to verify the proposed mechanism.

Keywords:Bis-indolylmethanes;Ionic liquids;Indoles;Aldehydes;Ketones;Green chemistry

[References]

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[Referenced By]

[1] Lingens F, Goebel W, Biochim. Biophys. Acta Gen. Subj., 148, 70 (1967)

[2] Fahy E, Potts BCM, Faulkner DJ, Smith K, J. Nat. Prod., 54, 564 (1991)

[3] Bao B, Sun Q, Yao X, Hong J, Lee CO, Sim CJ, Im KS, Jung JH, J. Nat. Prod., 68, 711 (2005)

[4] Diana P, Carbone A, Barraja P, Montalbano A, Martorana A, Dattolo G, Gia P, Via LD, Cirrincione G, Bioorg. Med. Chem. Lett., 17, 2342 (2007)

[5] Ichite N, Chougule MB, Jackson T, Fulzele SV, Safe S, Singh M, Clin. Cancer Res., 15, 543 (2009)

[6] Gong H, Jie ZF, Chin. J. Org. Chem., 32, 1195 (2012)

[7] Li JT, Sun MX, He GY, Xu XY, Ultrason. Sonochem., 18, 412 (2011)

[8] Ji SJ, Zhou MF, Gu DG, Jiang ZQ, Loh TP, Eur. J. Org. Chem., 2004, 1584 (2004)

[9] Ramesh C, Banerjee J, Pal R, Das B, Adv. Synth. Catal., 345, 557 (2003)

[10] Yadav JS, Reddy BVS, Murthy CVSR, Kumar GM, Madan C, Synthesis, 2001, 783 (2001)

[11] Tayebee R, Amini MM, Abdollahi N, Aliakbari A, Rabiei S, Ramshini H, Appl. Catal. A: Gen., 468, 75 (2013)

[12] Firouzabadi H, Iranpoor N, Jafarpour M, Ghaderi A, J. Mol. Catal. A-Chem., 253(1-2), 249 (2006)

[13] Pasha MA, Jayashankara VP, J. Pharm. Toxicol., 1, 585 (2006)

[14] Edayadulla N, Basavegowda N, Lee YR, J. Ind. Eng. Chem., http://dx.doi.org/10.1016/j.jiec.2014.06.007. (2014)

[15] Olivier-Bourbigou H, Magna L, Morvan D, Appl. Catal. A: Gen., 373(1-2), 1 (2010)

[16] Toma S, Meciarova M, Sebesta R, Eur. J. Org. Chem., 2009, 321 (2009)

[17] Lee S, Chem. Commun., 10, 1049 (2006)

[18] Zheng X, Qian YB, Wang Y, Eur. J. Org. Chem., 2010, 515 (2010)

[19] Tran PH, Duus F, Le TN, Tetrahedron Lett., 53, 222 (2012)

[20] Li ZF, Hou HL, Ying Ag, Xu SL, Chin. J. Org. Chem., 34, 1074 (2014)

[21] Xu DZ, Liu Y, Shi S, Wang YM, Green Chem., 12, 514 (2010)

[22] Mulla SAR, Sudalai A, Pathan MY, Siddique SA, Inamdar SM, Chavan SS, Reddy RS, RSC Adv., 2, 3525 (2012)

[23] Liu C, Yu CJ, Heterocycl. Chem., 48, 845 (2011)

[24] Chakraborti AK, Roy SR, Kumar D, Chopra P, Green Chem., 10, 1111 (2008)

[25] Fang D, Zhou XL, Ye ZW, Liu ZL, Ind. Eng. Chem. Res., 45(24), 7982 (2006)

[26] Zhang Q, Luo J, Wei Y, Green Chem., 12, 2246 (2010)

[27] Beyer KH, Bergfeld WF, Berndt WO, Boutwell RK, Carlton WW, Hoffmann DK, Schroeter AL, J. Am. Coll. Toxicol., 2, 183 (1983)

[28] Ying AG, Xu SL, Liu S, Ni YX, Yang JG, Wu CL, Ind. Eng. Chem. Res., 53(2), 547 (2014)

[29] Karthik M, Magesh CJ, Perumal PT, Palanichamy M, Arabindoo B, Murugesan V, Appl. Catal. A: Gen., 286(1), 137 (2005)

[30] Gibbs TJ, Tomkinson NC, Org. Biomol. Chem., 3, 4043 (2005)

[31] Satam JR, Parghi KD, Jayaram RV, Catal. Commun., 9, 1071 (2008)

[32] Thornazeau C, Olivier-Bourbigou H, Magna L, Luts S, Gilbert B, J. Am. Chem. Soc., 125(18), 5264 (2003)