Synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) via multi-component reactions by using silica-bonded sulfamic acid derivatives

Authors

1 Young Researchers Club, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.

2 Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169 Iran.

Abstract

The one-pot, multi-component synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) by tandem Knoevenagel-Michael reaction of phenylhydrazine, ethyl acetoacetate and aldehydes in the presence of silica-bonded N-propylpiperazine sulfamic acid (SBPPSA) as a recyclable solid acid catalyst was reported. SBPPSA showed much the same efficiency when used in consecutive reaction runs.

Keywords


[1] E. McDonald, K. Jones, P.A. Brough, M.J. Drysdale, P. Workman, Curr. Top. Med. Chem. 6 (2006) 1193-1203.

[2] J. Elguero, Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Eds, Vol. 5, Pergamon, Oxford 1996.

[3] J. Elguero, P. Goya, N. Jagerovic, A.M.S. Silva, Targets Heterocycl. Syst. 6 (2002) 52-98.

[4] I. H. Cho, J.Y. Noh, S.W. Park, H.C. Ryu, J.W. Lim, J.H. Kim, M.Y. Chae, D.H. Kim, S.H. Jung, H.J. Park, Y.H. Kim, I.K. Min, US Patent, (2004) 2,004, 002, 532.

[5] H.J. Park, K. Lee, S.J. Park, B. Ahn, J.C. Lee, H.Y. Cho, K.I. Lee, Bioorg. Med. Chem. Lett. 15 (2005) 3307-3312.

[6] M.P. Clark, S.K. Laughlin, M.J. Laufersweiler, R.G. Bookland, T.A. Brugel, A. Golebiowski, M.P. Sabat, J.A. Townes, J.C. VanRens, J.F. Djung, M.G. Natchus, B. De, L.C. Hsieh, S.C. Xu, R.L. Walter, M.J. Mekel, S.A. Heitmeyer, K.K. Brown, K. Juergens, Y.O. Taiwo, M.J. Janusz, J. Med. Chem. 47, (2004) 2724-2727.

[7] M.P. Clark, S.K. Laughlin, A. Golebiowski, T.A. Brugel, M. Sabat, WO Patent, (2005) 2, 005, 047, 287.

[8] 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.

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

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

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

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

[13] D. Singh, D. Singh, J. Indian Chem. Soc. 68 (1991) 165-167.

[14] W.S. Hamama, Synth. Commun. 31 (2001) 1335-1345.

[15] X.L. Li, Y.M. Wang, B. Tian, T. Matsuura, J.B. Meng, J. Heterocycl. Chem. 35 (1998) 129-134.

[16] D. Singh, D. Singh, J. Chem. Eng. Data 29 (1984) 355-356.

[17] P.T. Pavlov, A.F. Goleneva, A.E. Lesnov, T.S. Prokhorova, Pharm. Chem. J. (Engl. Trans.) 32 (1998) 370-372.

[18] B.I. Buzykin, T.I. Lonshchakova, Bull. Acad. Sci. USSR, Div. Chem.Sci. (Engl. Trans.) (1971) 2224-2226.

[19] W. Wang, S.X. Wang, X.Y. Qin, J.T. Li, Synth. Commun. 35 (2005) 1263-1269.

[20] M.N. Elinson, A.S. Dorofeev, R.F. Nasybullin, G.I. Nikishin, Synthesis (2008) 1933-1937.

[21] K. Sujatha, G. Shanthi, N.P. Selvam, S. Manoharan, P.T. Perumal, M. Rajendran, Bioorg. Med. Chem. Lett. 19 (2009) 4501-4503.

[22] E. Mosaddegh, A. Hassankhani, A. Baghizadeh, J. Chil. Chem. Soc. 55 (2010) 419-420.

[23] K. Niknam, D. Saberi, M. Sadegheyan, A. Deris, Tetrahedron Lett. 51 (2010) 692-694.

[24] K. Niknam, S. Mirzaee, Synth. Commun. 41 (2011) 2403-2413.

[25] S. Tayebi, M. Baghernejad, D. Saberi, K. Niknam, Chin. J. Catal. 32 (2011) 1477-1483.

[26] K. Niknam, A. Deris, F. Naeimi, F. Majleci, Tetrahedron Lett. 52 (2011) 4642-4645.

[27] K. Niknam, M.R. Mohammadizadeh, S. Mirzaee, D. Saberi, Chin. J. Chem., 28 (2010) 663-669.

[28] K. Niknam, M.R. Mohammadizadeh, S. Mirzaee, Chin. J. Chem., 29 (2011) 1417-1422.

[29] K. Niknam, D. Saberi and M. Nouri Sefat, Tetrahedron Lett. 51 (2010) 2959-2962.

[30] M. Nouri Sefat, D. Saberi, K. Niknam, Catal. Lett., 141 (2011) 1713-1720.

[31] K. Niknam, D. Saberi, Appl. Catal. A: Gen., 366 (2009) 220-225.

[32] K. Niknam, D. Saberi, M. Baghernrjad, Chin. Chem. Lett., 20 (2009) 1444-1448.

[33] M. Nouri Sefat, A. Deris, K. Niknam, Chin. J. Chem., 29 (2011) 2361-2367.

[34] F. Rohandeh, D. Saberi, K. Niknam, Iran. J. Catal. 1 (2011) 71-78.

[35] M. Baghernejad, K. Niknam, In. J. Chem. 4 (2012) 52-60.