Synthesis of 1,3,5-tri-substituted pyrazoles promoted by P2O5.SiO2

Authors

1 Department of Organic Chemistry, Faculty of Chemistry, University of Kashan , Kashan, I.R.Iran.

2 Department of Chemistry, College of Science, Yazd University, P.O.Box 89195-741, Yazd, I.R.Iran.

Abstract

Silica supported phosphorus pentoxide (P2O5·SiO2) is an efficient catalyst for synthesis of 1,3,5-substituted pyrazoles via the condensation of 1,3-diketones and hydrazines. Simplicity of procedure, mild condition, being solvent-free, high yields, and easy workup are some advantages of this protocol.

Keywords


[1] N. Gokhan-Kelekci, S. Yabanoglu, E. Kupeli, U. Salgin, O. Ozgen, G. Ucar, E. Yesilada, E. Kendi, A. Yesilada, A.A. Bilgin, Bioorg. Med. Chem. 15 (2007) 5775-5786.

[2] C.L. Behr, R. Fusco, C.H. Jarboe, The Chemistry of Heterocyclic Compounds, Pyrazoles, Pyrazolines,

Pyrazolidines, Indazoles and Condensed Rings, A. Weissberger, Ed. Interscience Publishers: New York, 1967.

[3] C.E. Rosiere, M.I. Grossman, Science. 113 (1951) 651-651.

[4] D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J.Pearl, A.F. Defelice, M.E. Feigenson, J. Med. Chem. 28 (1985) 256-260.

[5] F.H.H. Leenen, D.L. Smith, W.P. Unger, Br. J. Clin. Pharmacol. 26 (1988) 481-485.

[6] R.N. Mahajan, F.H. Havaldar, P.S. Fernandes, J. Indian Chem. Soc. 68 (1991) 245-246.

[7] F. Lepage, B. Hubiot, Eur. Pat. Appl. EP, 459, 887; Chem. Abstr. 116 (1992) 128914.

[8] R. Lin, G. Chiu, Y. Yu, P.J. Connolly, S.Li, Y. Lu, M. Adams, A.R. Fuentes-Pesquera, S.L. Emanuel, L.M. Greenberger, Bioorg. Med. Chem. Lett. 17 (2007) 4557-4561.

[9] M. Barcelo, E. Ravina, C.F. Masaguer, E. Domínuez, F.M. Areias, J. Brea, M.I. Loza, Bioorg. Med. Chem. Lett. 17 (2007) 4873-4877.

[10] A.M. Farag, A.S. Mayhoub, S.E. Barakat, A.H. Bayomi, Bioorg. Med. Chem. 16 (2008) 4569-4578.

[11] J.D. Larsen, M.A. Zahran, E.B. Pedersen, C. Nielsen, Monatsh. Chem. 130 (1999) 1167-1173.

[12] P.M.S. Chauhan, S. Singh, R.K. Chatterjee, Indian J. Chem. B 32 (1993) 858-861.

[13] G.G.A. Dutra, B.C. Hamper, D.A. Mischke, K. Moedritzer, M.D. Rogers, PCT Int. Appl. WO 8206, 962, Chem. Abstr. 1992, 117, 69859.

[14] B. Natsume, N. Kyomura, K. Kikutake, T. Fukuch, Eur. Pat. Appl. EP. 462, 573.

[15] M. Londershausen, Pestic. Sci. 48 (1996) 269-292.

[16] S.M. Fahmy, A.H. Badran, M.H. Elnagdi, J. Chem Tech. B: Technol. 30 (1980) 390-395.

[17] M. Windholz, Ed., The Merk Index, 9th ed.; Merck and Co., Rahway: New Jersey, 1976, 8851.

[18] V.K. Aggarwal, C.V. Vicente, R.V. Bonnert, J. Org. Chem. 68 (2003) 5381-5383.

[19] B.A. Bhat, S.C. Puri, M.A. Qurishi, K L. Dhar, G.N.G. N. Qazi, Synth. Commun. 35 (2005) 1135-1142.

[20] M.S. M.Ahmed, K. Kobayashi, A. Mori, Org. Lett. 7 (2005) 4487-4489.

[21] S. Fustero, R. Roman, J.F.X. Sanz-Cervera, A. Simon-Fuentes, A.C. Cunat, S. Villanova, M. Murguía, J. Org. Chem. 73 (2008) 3523-3529.

[22] Z. Wang, H. Qin, Green Chem. 6 (2004) 90-92.

[23] V. Polshettiwar, R. S. Varma, Tetrahedron Lett. 49 (2008) 397.

[24] M. Curini, O. Rosati, V. Campagna, F. Montanari, G. Cravotto, M. Boccalini, Synlett. 19 (2005) 2927-2930.

[25] W. Xiong, J.X. Chen, M.C. Liu, J.C. Ding, H.Y. Wu, W.K. Su, J. Braz. Chem. Soc. 20 (2009) 367-374.

[26] R. Sreekumar, R. Padmakumar, Synth.Commun. 28 (1998) 1661-1665.

[27] B.F. Mirjalili, A. Bamoniri, M.A. Amrollahi, H. Emtiazi, Digest J. Nanomat. Biostruct. 5 (2010) 897-902.

[28] B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, M.A. Amrollahi, A. Hazar, Phosphorus Sulfur, 179 (2004) 1397-1401.

[29] B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, Phosphorus, Sulfur, and Silicon 179 (2004) 19-24.

[30] H. Eshghi, Z. Gordi, Phosphorus Sulfur, 180 (2005) 1553-1557.

[31] B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, L. Khazdooz, Bull. Korean Chem. Soc. 24 (2003) 1-2.

[32] A.R. Hajipour, A.E. Ruoho, Tetrahedron Lett. 46 (2005) 8307-8310.

[33] F. Tamaddon, M. Khoobi, E. Keshavarz, Tetrahedron Lett. 48 (2007) 3643-3646.

[34] H. Eshghi, A. Hassankhani, Synth. Commun. 36 (2006) 2211-2216.

[35] A. Hasaninejad, A. Zare, H. Sharghi, K. Niknam, M. Shekouhy, ARKIVOC. 15 (2007) 39-50.

[36] A. Bamoniri, B.F. Mirjalili, A. Ghorbani-Ch., M.E. Yazdanshenas, A. Shayanfar, A. Akbari, Iran. J. Catal. 1 (2011) 51-54.

[37] B.F. Mirjalili, A. Bamoniri, A. Akbari, Iran. J. Catal. 1 (2011) 87-92.