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

Authors

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

DOI:

https://doi.org/10.29356/jmcs.v59i1.6

Keywords:

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

Abstract

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.

Downloads

Download data is not yet available.

References

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.

Published

2017-10-12

Issue

Vol. 59 No. 1 (2015): Regular Issue

Section

Regular Articles

License

Authors who publish with this journal agree to the following terms:

  • Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
  • Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.