Synthesis of Pyranopyrazole Compounds Using Heterogeneous Base Catalyst Based on 1,3,5-Triazine-2,4,6-Triamine Modified Nano Rice Husk Silica
محورهای موضوعی : Journal of NanoanalysisJamal Davarpanah 1 , Reza Khoram 2
1 - Chemistry Department, Production Technology Research Institute-ACECR, Ahvaz, Iran
2 - Chemistry Department, Omidiyeh Branch, Islamic Azad University, Omidiyeh, Iran
کلید واژه: Heterogeneous catalyst, Rice husk silica, Pyranopyrazole, Melamine catalyst,
چکیده مقاله :
In the current study, amorphous silica nanoparticles were easily extracted from rice husk ash. The target composite was synthesized by the direct incorporation of chloropropyl groups through the condensation of nanosilica and 3-chloropropyl trimethoxysilane and then grafting of 1,3,5-triazine-2,4,6-triamine (Melamine) onto the propyl groups by the simple nucleophilic substitution reaction (RHA@Melamine). The resulting solid catalyst was characterized by infrared spectroscopy, scanning electron microscope and thermogravimetric analysis. The catalytic activity of this solid acid nanocomposite was probed through one-pot synthesis of 1,4-dihydropyrano[2,3-c] pyrazole via four-component couplings of aldehydes, hydrazine hydrate, ethyl acetoacetate and malononitrile under solvent-free conditions. In this reaction, RHA@Melamine shows good catalytic nature, easy to handle procedure, recycle exploitation and excellent isolated yields of products.
1. J. Weitkamp, M. Hunger, U. Rymsa, Microporous Mesoporous Mater., 48 (2001) 255-270
2. P.S.E. Dai, Catal. Today, 26 (1995) 3-11
3. T. Baba, A. Kato, H. Takahashi, F. Toriyama, H. Handa, Y. Ono, H. Sugisawa, J. Catal., 176 (1998) 488-494
4. A. B'eres, I. P'alink'o, I. Kiricsi, J.B. Nagy, Y. Kiyozumi, F. Mizukami, Appl. Catal. A, 182 (1999) 237-247
5. O. Lanitou, D. Dimotikali, E. Yannakopoulou, K. Papadopoulos, Chem. Eng. J., 134 (2007) 72-77
6. S. Sahoo, P. Kumar, F. Lefebvre, S.B. Halligudi, Tetrahedron Lett., 49 (2008) 4865-4868
7. H. Paul, S. Basu, S. Bhaduri, G.K. Lahiri, J. Org. Chem., 689 (2004) 309-316
8. J. Wang, L. Huang, M. Xue, L. Liu, Y. Wang, L. Gao, J. Zhu, Z. Zou, Appl. Surf. Sci., 254 (2008) 5329-5335
9. E.F.C. Alcaˆntara, E.A. Faria, D.Y. Rodrigues, S.M. Evangelista, E. DeOliveira, L.F. Zara, D. Rabelo, A.G.S. Prado, J. Colloid Interface Sci., 31 (2007) 1-7
10. D. Brunel, Microporous Mesoporous Mater., 27 (1999) 329-344
11. G. Barcelo, D. Grenouillat, J.P. Senet, G. Sennyey, Tetrahedron, 46 (1990) 1839-1898
12. D.J. Macquarrie, D.B. Jackson, Chem. Commun., 18 (1997) 1781-1782
13. K.A. Utting, D.J. Macquarrie, New J. Chem., 24 (2000) 591-595
14. D. Brunel, F. Fajula, J.B. Nagy, B. Deroide, M.J. Verhoef, L. Veum, J.A. Peters, H. Van Bekkum, Appl. Catal. A: Gen., 213 (2001) 73-82
15. A.R. Kiasat, S. Nazari, J. Davarpanah, C. R. Chimie, 17 (2014) 124-130
16. J. Davarpanah, A.R. Kiasat, RSC Adv., 4 (2014) 4403-4412
17. F. Adam, K.M. Hello, H. Osman, Appl. Catal. A, 365 (2009) 165-172
18. I. Rodriguez, S. Iborra, A. Corma, F. Rey, J.L. Jorda, Chem.Commun., 7 (1999) 593-594
19. A. Stein, Adv. Mater. Weinheim. Ger., 15 (2003) 763-775
20. I.K. Mbaraka, D.R. Radu, V.S. Lin, B.H. Shanks, J. Catal., 219 (2003) 329-336
21. S. Dai, M. Burleigh, Y. Shin, C.C. Morrow, C.E. Barnes, Z. Xue, Angew. Chem., Int. Ed. Engl., 38 (1999) 1235-1239
22. H. Yoshitake, T. Yokoi, T. Tatsumi, Chem. Mater., 15 (2003) 1713-1721
23. V.S.Y. Lin, C.Y. Lai, J. Huang, S.A. Song, S. Xu, J. Am. Chem. Soc., 123 (2001) 11510-11511
24. A.E. Ahmed, F. Adam, Microporous Mesoporous Mater., 118 (2009) 35-43
25. F. Adam, A. Iqbal, Microporous Mesoporous Mater., 141 (2011) 119-127
26. V.P. Della, I. Kuhn, D. Hotza, Mater. Lett., 57 (2002) 818-821
27. N. Pijarn, A. Jaroenworaluck, W. Sunsaneeyametha, R Stevens. Powder Technol., 203 (2010) 462-468
28. J. Davarpanah, A.R. Kiasat, RSC Adv., 5 (2015) 7986-7993
29. J. Davarpanah, A.R. Kiasat, Catal. Commun., 46 (2014) 75-80
30. A. Feurer, J. Luithle, S. Wirtz, G. Koenig, J. Stasch, E. Stahl, R. Schreiber, F. Wunder, D. Lang, PCT Int. Aool. Wo2004009589, BayeHealtheare Ag, Germany.
31. M.N. Nasr, M.M. Gineinah, Arch. Pharm. Med. Chem., 335 (2002) 289-295
32. V.K. Ahluwalia, A. Dahiya, V. Garg, Indian J. Biochem. Biophys., 36 (1997) 88-91
33. N. Foloppe, I.M. Fisher, R. Howes, A. Potter, A.G.S. Robertson, A.E. Surgenor, Bioorg. Med. Chem., 14 (2006) 4792-4802
34. (a) M.E.A. Zaki, E.M. Morsy, M. Abdul, Heterocycl. Commun., 10 (2004) 97-102 (b) J.L. Wang, D. Liu, Z.J. Zheng, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci., U.S.A., 97 (2009) 7124-7129
35. N. Mishriky, A.S. Girgis, F.M. Asaad, Y.A. Ibrahim, U.I. Sobieh, N.G. Fawzy, Boll. Chim. Farm., 140 (2001) 1129-139
36. (a) H.H. Otto, H. Schmelz, Arch. Pharm., 312 (1979) 478-486
37. D. Shi, J. Mou, Q. Zhuang, L. Niu, N. Wu, X. Wang, Synth. Commun., 34 (2004) 4557-4563
38. T.S. Jin, R.Q. Zhao, T.S. Li, Arkivoc, xi (2006) 176-182
39. H.V. Chavan, S.B. Babar, R.U. Hoval, B.P. Bandgar, Bull. Korean Chem. Soc., 32 (2011) 3963-3966
40. M.A. Zolfigol, M. Tavasoli, A.R. Moosavi-Zare, P. Moosavi, H.G. Kruger, M. Shiri, V. Khakyzadeh, RSC Adv., 3 (2013) 25681-25685
41. Z. Karimi-Jaberi, M.M.R. Shams, B. Pooladian, Acta Chim. Slov., 60 (2013) 105 -108
