Journal of Industrial and Engineering Chemistry, Vol.19, No.1, 337-346, January, 2013
Mn/Al2O3 and Mn/ZrO2 as selective catalysts for the synthesis of bis(indolyl)methanes: The role of surface acidity and particle morphology
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Mn/Al2O3 and Mn/ZrO2 were prepared by precipitation method. Their catalytic activity was investigated in the synthesis of biologically important bis(indolyl)methanes via, a condensation reaction between an indole and different aldehydes. The materials exhibited excellent catalytic activity (TOF in the range 180-380 h^(-1)) and produced the expected product in good yield and selectivity. Isolation of product from the reaction mixture was simple and neat. The catalysts were found to be recyclable and used up to five cycles without any loss in their catalytic activity. Mn/ZrO2 was also found to be a better catalyst than Mn/Al2O3 in terms of isolated yield of the product and recyclability. Mn/ZrO2 catalyst was found to be selective for aldehydes and not for ketones. In order to investigate the relationship between the catalytic activity and physico-chemical properties, Mn/Al2O3 and Mn/ZrO2 were characterized for their surface and bulk properties by PXRD, BET, TPD-NH3 and SEM techniques. A good correlation between the catalytic activity of the materials and the concentration of the acid sites with intermediate strength was observed. Mn/ZrO2 exhibited rod like structure. This material was found to be a general catalyst for the synthesis of a number of bis(indolyl)methane derivatives with good yield and selectivity.
- Davis ME, Microporous and Mesoporous Materials., 21, 173 (1998)
- Kozhevnikov IV, Chem. Rev., 98(1), 171 (1998)
- Nagendrappa G, Applied Clay Science., 53, 106 (2011)
- Thakuria H, Borah BM, Das G, J. Mol. Catal. A-Chem., 274(1-2), 1 (2007)
- Gaigneaux EM, Devillers M, Hermans S, Jacobs PA, Martens JM, Ruiz P, in: Proceedings of the 10th international symposium, Louvain-la-neuvie, Belgium, July 11-15 (2010)
- Trueba M, Trasatti SP, European Journal of Inorganic Chemistry., 17, 3393 (2005)
- Reddy BM, Patil MK, Chem. Rev., 109(6), 2185 (2009)
- Nagaraju N, Kuriakose G, Green Chemistry., 4, 269 (2002)
- Mathew S, Kathyayini H, Nagy JB, Nagaraju N, Catalysis Communications., 10, 1043 (2009)
- Tumma H, Nagaraju N, Reddy KV, J. Mol. Catal. A-Chem., 310(1-2), 121 (2009)
- Vijayasankar AV, Deepa S, Venugopal BR, Nagaraju N, Chinese Journal of Catalysis., 31, 1321 (2010)
- Rekha M, Hamza A, Venugopal BR, Nagaraju N, Chinese Journal of Catalysis., 33, 438 (2012)
- Garbe TR, Kobayashi M, Shimizu N, Takesue N, Ozawa M, Yukawa H, Journal of Natural Products., 63, 596 (2000)
- Fukuyama T, Chen XQ, Peng G, J. Am. Chem. Soc., 116(7), 3127 (1994)
- Shilling AD, Carlson DB, Katchamart S, Williams D, Toxicology and Applied Pharmacology., 170, 191 (2001)
- Qu HE, Xiao C, Wang N, Yu KH, Hu QS, Liu LX, Molecules., 16, 3855 (2011)
- Ramesh C, Banerjee J, Pal R, Das B, Advanced Synthesis and Catalysis., 34, 557 (2003)
- Dabiri M, Baghbanzadeh M, Nikcheh MS, Arzroomchilar E, Bioorganic & Medicinal Chemistry Letters., 18, 436 (2008)
- Balaskar RS, Shingate BB, Shingare MS, Mane DV, Arabian Journal of Chemistry., 4, 349 (2011)
- Kidwai M, Bura N, Mishra NK, Indian Journal of Chemistry., 50, 229 (2011)
- Sadaphal SA, Kategaonkar AH, Labade VB, Shingare MS, Chinese Chemical Letters., 21, 39 (2010)
- Tayebee R, Nehzata F, Rezaei-Sereshta Esmail, Mohammadia FZ, Rafiee E, Journal of Molecular Catalysis A: Chemical., 351, 154 (2011)
- Shaikh AC, Chen C, Journal of the Chinese Chemical Society., 58, 899 (2011)
- Praveen C, Sagayaraj YW, Perumal PT, Tetrahedron Letters., 50, 644 (2009)
- Silveria C, Mendes SR, Libero FM, Lenardao EJ, Perin G, Tetrahedron Letters., 50, 6060 (2009)
- Nagarajan R, Perumal PT, Chem. Lett., 33(3), 288 (2004)
- Nadkarni SV, Gawande MB, Jayaram RV, Nagarkar JM, Catalysis Communications., 9, 1728 (2008)
- Ji SJ, Wang SY, Zhang Y, Loh TP, Tetrahedron., 60, 2051 (2004)
- Kobayashi S, Araki M, Yasuda M, Tetrahedron Letters., 36, 5773 (1995)
- Liu Y, Ma D, Han X, Bao X, Frandsen W, Wang D, Su D, Materials Letters., 62, 1297 (2008)
- Wefers K, Misra C, Aloca Technical Paper., 19, 54 (1987)
- Kim SC, Shim WG, Appl. Catal. B: Environ., 98(3-4), 180 (2010)
- Wang WM, Yang YN, Zhang JY, Appl. Catal. A: Gen., 131(2), 189 (1995)
- Breitkopf C, Garsuch A, Papp H, Applied Catalysis A., 296, 148 (2005)
- Collins DE, Rogers KA, Bowman KJ, Journal of the European Ceramic Society., 15, 1119 (1995)
- Martin PF, Matthias B, Guido K, Olga M, Ulrich S, Helmut B, Journal of Non-Crystalline Solids., 351, 432 (2005)
- Rubio E, Rodriguez-Lugo V, Rodriguez R, Castano VM, Reviews on Advanced Materials Science., 22, 67 (2009)
- Sakthivel R, Prescott H, Kemnitz E, J. Mol. Catal. A-Chem., 223(1-2), 137 (2004)
- Mohamed Shamshuddin SZ, Nagaraju N, Journal of Chemical Sciences., 122, 193 (2010)
- Quinelato AL, Longo E, Leite ER, Bernardi MIB, Varela JA, J. Mater. Sci., 36(15), 3825 (2001)
- Valmalette JC, Isa M, Chemistry of Materials., 14, 5098 (2002)
- Clothup NB, Daly LH, Wiberley SE, Introduction to Infrared and Raman Spectroscopy, second ed., Academic Press, New York (1975)
- Zhu XM, Li XM, Jia MJ, Liu G, Zhang WX, Jiang DZ, Appl. Catal. A: Gen., 282(1-2), 155 (2005)
- Einaga H, Harada M, Ogata A, Catal. Lett., 129(3-4), 422 (2009)
- Zhao Q, PhD Thesis, Drexel University, Philadelphia, USA (2004)
- Parida KM, Mallick S, J. Mol. Catal. A-Chem., 279(1), 104 (2008)
- Firouzabadi H, Iranpoor N, Jafari AA, J. Mol. Catal. A-Chem., 244(1-2), 168 (2006)
- Reddy AV, Ravinder K, Reddy VLN, Goud TV, Ravikanth V, Venkateswaralu Y, Synthetic Communications., 33, 3687 (2003)
- Kantam ML, Laha S, Yadav J, Sreedhar B, Tetrahedron Letters., 47, 6213 (2006)
- Yadav JS, Subba reddy BV, Murthy VSR, Mahesh Kumar G, Madan C, Synthesis., 5, 783 (2001)
- Remers W, Chemistry of Heterocyclic Compounds., 25, 1 (1972)