A Rapid, One-pot, Multi-component Route to 4,4’-(arylmethylene)bis(3methyl1-1-phenyl-H-pyrazol-5-ols)


  • Asadollah Hassankhani Department of New Materials Science, Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology




Ce(SO4)2.4H2O, 4, 4'-arylmethylene-bis(3-methyl-1-phenyl-1H-pyrazol-5-ols), heterogeneous catalyst, environmentally friendly, solvent-free conditions


A new, efficient and environmentally benign protocol for the one-pot, multicomponent synthesis of 4,4'-arylmethylene-bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) by condensation of aryl aldehydes, phenyl hydrazine and ethyl acetoacetate catalyzed by Ce(SO4)2.4H2O as an ecofriendly catalyst with high catalytic activity and reusability at 125 °C under solvent-free conditions is reported.

The reaction proceeds to completion within 5-12 min in 81-98% yield. This new green methodology is of interest due to minimizing the cost of operational hazards and environmental pollution, its excellent yields, short reaction time and high catalyst activity and reusability.


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Anastas, P.T.; Warner, J.C. Green Chemistry: Theory and Practice. Oxford University Press: Oxford, 1998.

Mekheimer, R.A.; Abdelhameed, A.M.; Mohamed, S.M.; Sadek, K.U. Green Chem. Lett. Rev.2010, 3, 161-163.

Domling, A. Chem. Rev. 2006, 106, 17-89.

Burke, M.D.; Schreiber, S.L. Angew. Chem. Int. Ed.2004, 43, 46-58.

Park, H.J.; Lee, K.; Park, S.J.; Ahn, B.; Lee, J.C.; Cho, H.Y.; Lee, K.I. Bioorg. Med. Chem. Lett. 2005, 15, 3307-3312.

Clark, M.P.; Laughlin, S.K.; Laufersweiler, M.J.; Bookland, R.G.; Brugel, T.A.; Golebiowski, A.; Sabat, M.P.; Townes, J.A.; VanRens, J.C.; Djung, J.F.; Natchus, M.G.; De, B.; Hsieh, L.C.; Xu, S.C.; Walter, R.L.; Mekel, M.J.; Eitmeyer, S.A.; Brown, K.K.; Juergens, K.; Taiwo, Y.O.; Janusz, M.J. J. Med. Chem. 2004, 11, 2724-2727.

Cho, I.-H.; Noh, J.-Y.; Park, S.-W.;Ryu, H.-C.; Lim, J.-W.; Kim, J.-H.;Chae, M.-Y.; Kim, D.-H.; Jung, S.-H.; Park, H.-J.; Kim, Y.-H.; Min, I.-K. WO Patent 2004000206,2003.

Clark, M.P.; Laughlin, S.K.;Golebiowski, A.;Brugel, T.A.;Sabat, M. WO Patent 2005047287,2005.

Rosiere, C. E.; Grossman, M. I.Science. 1951, 113, 651-651.

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

Mahajan, R.N.; Havaldar, F.H.; Fernandes, P.S. J. IndianChem. Soc. 1991, 68, 245-246.

Chauhan, P.M.S.; Singh, S.; Chatterjee, R.K. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1993, 32, 858-861.

Singh, D.; Singh, D.J. J. Indian Chem. Soc. 1991, 68, 165-167.

Londershausen, M. Pestic. Sci. 1996, 48, 269-292.

Lubs, H.A. The Chemistry of Synthetic Dyes and Pigments.

American Chemical Society: Washington D.C., 1970.

(a) Uzoukwu, B.A.; Al-Juaid, S.S.; Hitchcock, P.B.; Smith, J.D. Polyhedron1993, 12, 2719-2724. (b) Maurya, R.C.; Verma, R. Indian J. Chem. Sect. A 1997, 36, 596-598. (c) Garnovskii, A.D.; Uraev, A.I.; Minkin, V.I. Arkivoc 2004, 3, 29-41.

(a) Hassankhani, A.; Mosaddegh, E.; Ebrahimipour, Y. Arab. J. Chem. in press. (b) Mosaddegh, E.;Hassankhani, A. Tetrahedron Lett. 2011, 52, 488-490. (c)Mosaddegh, E.; Hassankhani, A.Catal.Commun.2013, 33, 70–75.

Stefan, S. L.; El-Behary, M.; Ramadan, A.A; Mahmoud, S.A. J. Chem. Res. Miniprint1992, 1951.

Ahluwalia, V. K.; Sharma, P.; Goyal, B. Indian J. Chem. Sect. B. Org. Chem. Incl. Med. Chem.1997, 36, 1059.

(a) Hamama, W.S. Synth. Commun.2001, 31, 1335-1345 (b) Li, X.L.; Wang, Y.M.; Tian, B.; Matsuura, T.; Meng, J.B. J. Heterocycl. Chem. 1998, 35, 129-134.

(a) Singh, D.; Singh, D. J. Chem. Eng. Data.1984, 29, 355-356 (b) Mitra, A.S.; Rout, M.K. J. Indian Chem. Soc.1961, 38, 893-895.

Pavlov, T.; Goleneva, A.F.; Lesnov, A.E.; Prokhorova, T.S. Pharm. Chem. J. 1998, 32, 370-372.

Buzykin, B. I.; Lonshchakova, T.I. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1971, 2340-2342.

Li, L.; Ma, H.-r; Wang, Y.-m.; Meng, J.-b. Chem. J. Chin. Univ. 1995, 12, 1903-1910.

Bai, Y.-j.; Lu, J.; Gan, H.-y.; Wang, Z.-j.; Ma, H.-r. Chin. J. Org. Chem. 2002, 22, 638-641.

Shi, D.Q.; Chen, J.; Wu, N.; Zhuang, Q.Y.; Wang, X-S. Chin. J. Org. Chem.2005, 25, 405-408.

Wang, W.; Wang, S.-X.; Qin, X.-Y.; Li, J.-T. Synth. Commun. 2005, 35, 1263-1269.

Elinson, M.N.; Dorofeev, A.S.; Nasybullin, R.F.; Nikishin, G.I. Synthesis. 2008, 1933-1937.

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

Moosavi-Zare, A. R.; Zolfigol, M. A.; Zarei, M.;Zare, A.; Khakyzadeh, V.; Hasaninejad, A.Appl.Catal. A: Gen,2013,467, 61-68.

Niknam, K.; Saberi, D.; Sadegheyan, M.; Deris, A. Tetrahedron Lett. 2010, 51, 692-694.

Karimi-Jaberi, Z.;Pooladian, B.;Moradi, M.;Ghasemi, E. Chin. J. Catal. 2012, 33,1945-1949.

Zang, H.; Su, Q.; Mo, Y.; Cheng, B. Ultrason. Sonochem.2011, 18, 68-72.

Babaie, M.; Sheibani, H. Arab. J. Chem. 2011, 4, 159-162.

Sobhani, S.; Hasaninejad, A.-R.; Maleki, M.-F.; Mahdi, F.;Parizi, Z.P.Synth. Commun. 2012, 42, 2245–2255.

Sobhani, S.; Safaei, E.; Hasaninejad, A.-R..; Rezazadeh, S. J. Organomet. Chem. 2009, 694, 3027-3031.





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