Synthesis of Pyranopyrazole Compounds Using Heterogeneous Base Catalyst Based on 1,3,5-Triazine-2,4,6-Triamine Modified Nano Rice Husk Silica

Subject Areas : Journal of Nanoanalysis

Jamal 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

Received: 2017-07-05 Accepted : 2017-07-05 Published : 2017-03-01

Keywords: Heterogeneous catalyst, Rice husk silica, Pyranopyrazole, Melamine catalyst,

Abstract :

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.

References:

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