One pot three-component imino Diels–Alder reactions of various types of aldehydes, aniline and dihydropyrane were studied in the presence of nano sized MCM-41 supported 12-tungstophosphoric acid (TPA) as solid acid catalyst. MCM-41 as solid support was synthesized in nano size and the catalysts with different loading amounts of TPA (5–30 wt%) were prepared and characterized by XRD, FT-IR and SEM techniques. The results confirm a good dispersion of the heteropoly acid on the solid supports and based on the experimental results, the catalyst with 10 wt% heteropoly acid shows the best catalytic activity using 0.5 mol% heteropoly acid relative to the aldehyde. The recovery experiments show that the catalyst is reusable after calcination without significant loss in its activity.
Jacquemond-Collet, I, Benoit-Vical, F, Mustofa, V, Valentin, A, Stanislas, E, Mallié, M, Fourasté, I (2002) Planta Med 68:68 .
Wallace, OB, Lauwers, KS, Jones, SA, Dodge, JA (2003) Bioorg Med Chem Lett 13 11 1907 .
Dorey, G, Lockhart, B, Lestage, P, Casara, P (2000) Bioorg Med Chem Lett 10 9 935 .
Yamada, N, Kadowaki, S, Takahashi, K, Umezu, K (1992) Biochem Pharmacol 44 6 1211 .
Ramesh, M, Mohan, PS, Shanmugam, P (1984) Tetrahedron 40 20 4041 .
Srinivasa, A, Mahadevan, KM, Hosamani, KM, Hulikal, V (2008) Monatsh für Chem 139 2 141 .
Nagaiah, K, Sreenu, D, Rao, RS, Vashishta, G, Yadav, JS (2006) Tetrahedron Lett 47 26 4409 .
Xing, X, Wu, J, Dai, W-M (2006) Tetrahedron 62 48 11200 .
Nagarajan, R, Chitra, S, Perumal, PT (2001) Tetrahedron 57 16 3419 .
Ma, Y, Qian, C, Xie, M, Sun, J (1999) J Org Chem 64 17 6462 .
Zubkov, FI, Zaitsev, VP, Piskareva, AM, Eliseeva, MN, Nikitina, EV, Mikhailova, NM, Varlamov, AV (2010) Russ J Org Chem 46 8 1192 .
Kamble, VT, Davane, BS, Chavan, SA, Muley, DB, Atkore, ST (2010) Chin Chem Lett 21 3 265 .
Jin, GF, Zhao, JW, Han, JW, Zhu, SZ, Zhang, JM (2010) Tetrahedron 66 4 913 .
Kouznetsov, VV, Merchan Arenas, DR, Romero Bohórquez, AR (2008) Tetrahedron Lett 49 19 3097 .
Khadem, S, Udachin, KA, Enright, GD, Prakesch, M, Arya, P (2009) Tetrahedron Lett 50 48 6661 .
Ramesh, E, Vidhya, TKS, Raghunathan, R (2008) Tetrahedron Lett 49 17 2810 .
Chen, XM, Wei, H, Yin, L, Li, XS (2010) Chin Chem Lett 21 7 782 .
Wang, XS, Zhou, J, Yang, K, Yao, CS (2010) Tetrahedron Lett 51 43 5721 .
Abdollahi-Alibeik, M, Mohammadpoor-Baltork, I, Zaghaghi, Z, Yousefi, BH (2008) Catal Commun 9 15 2496 .
Dias, AS, Pillinger, M, Valente, AA (2006) Microporous Mesoporous Mater 94 1–3 214 .
Pizzio, LR, Vázquez, PG, Cáceres, CV, Blanco, MN (2003) Appl Catal A Gen 256 1–2 125 .
Abdollahi-Alibeik, M, Zaghaghi, Z, Mohammadpoor-Baltork, I (2008) J Chin Chem Soc 55 1 1.
Edwards, JC, Thiel, CY, Benac, B, Knifton, JF (1998) Catal Lett 51 1 77 .
Devassy, BM, Lefebvre, F, Halligudi, SB (2005) J Catal 231 1 1 .
Kresge, CT, Leonowicz, ME, Roth, WJ, Vartuli, JC, Beck, JS (1992) Nature 359 6397 710 .
Juan, JC, Zhang, J, Yarmo, MA (2007) J Mol Catal A Chem 267 1–2 265 .
Rabindran Jermy, B, Pandurangan, A (2008) Catal Commun 9 5 577 .
Jin, D, Hou, Z, Luo, Y, Zheng, X (2006) J Mol Catal A Chem 243 2 233 .
Ajaikumar, S, Pandurangan, A (2008) J Mol Catal A Chem 286 1–2 21 .
Vázquez, P, Pizzio, L, Cáceres, C, Blanco, M, Thomas, H, Alesso, E, Finkielsztein, L, Lantaño, B, Moltrasio, G, Aguirre, J (2000) J Mol Catal A Chem 161 1–2 223 .
Kozhevnikov, IV (2007) J Mol Catal A Chem 262 1–2 86 .
Kozhevnikov, IV (2009) J Mol Catal A Chem 305 1–2 104 .
Karthikeyan, G, Pandurangan, A (2009) J Mol Catal A Chem 311 1–2 36 .
Udayakumar, S, Ajaikumar, S, Pandurangan, A (2007) Catal Commun 8 3 366 .
Carriazo, D, Domingo, C, Martín, C, Rives, V (2008) J Solid State Chem 181 8 2046 .
Xia, QH, Hidajat, K, Kawi, S (2002) J Catal 209 2 433 .
López-Salinas, E, Hernández-Cortéz, JG, Cortés-Jácome, MA, Navarrete, J, Llanos, ME, Vázquez, A, Armendáriz, H, López, T (1998) Appl Catal A Gen 175 1–2 43 .
Dias, JA, Caliman, E, Dias, SCL, Paulo, M ATCP de Souza (2003) Catal Today 85 1 39 .