Synthesis and Characterization of Some Novel 4-Aryloxy Substituted Pyrazoles

Muhammad Sher; Pervaiz Ali; Zaman Ashraf; Muhammad Aamir; Ejaz Ahmed; Ahsan Sharif; Nadia Riaz; Shahid Iqbal

doi:10.14233/ajchem.2014.17172

Issue

Vol. 26 No. 21 (2014): Vol 26 Issue 21

Issue Published : September 30, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Characterization of Some Novel 4-Aryloxy Substituted Pyrazoles

https://doi.org/10.14233/ajchem.2014.17172

Muhammad Sher

Department of Chemistry, AllamaIqbal Open University, Islamabad-44000, Pakistan

Pervaiz Ali

Department of Chemistry, AllamaIqbal Open University, Islamabad-44000, Pakistan

Zaman Ashraf

Department of Chemistry, AllamaIqbal Open University, Islamabad-44000, Pakistan

Muhammad Aamir

Department of Chemistry, AllamaIqbal Open University, Islamabad-44000, Pakistan

Ejaz Ahmed

Institute of Chemistry, University of the Punjab, Quaid-e-Azam Campus, Lahore-54590, Pakistan

Ahsan Sharif

Institute of Chemistry, University of the Punjab, Quaid-e-Azam Campus, Lahore-54590, Pakistan

Nadia Riaz

Department of Chemistry, AllamaIqbal Open University, Islamabad-44000, Pakistan

Shahid Iqbal

Department of Chemistry, University of Sargodha, Sargodha 40100, Pakistan

Corresponding Author(s) : Ejaz Ahmed

dr.ejaz.ahmed@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 21 (2014): Vol 26 Issue 21
Article Published : October 1, 2014

Abstract

The synthesis of some novel 4-aryloxy substituted pyrazoles was performed in two steps. The synthetic route involves the synthesis of 3-aryloxy substituted 1,3-dicarbonyl compounds (3a-e) in first step by the condensation of 3-chloro-pentan-2,4-dione (1) and substituted phenols (2a-e). The hydrazine monohydrate/substituted aromatic hydrazides (4a-e) in the second step were then treated with compounds 3a-e to afford the target pyrazoles (5a-e). The interesting feature of this reaction is the isolation of the intermediate pyrazoline. The structure of this intermediate was also confirmed by the X-ray single crystal. The structures of the synthesized compounds 5a-e were assigned on the basis of FT-IR, ¹H NMR, ¹³C NMR and mass spectroscopic data.

Keywords

Hydrazides 4-Aryloxy pyrazoles 5-Hydoxy-2-pyrazoline

Sher, M., Ali, P., Ashraf, Z., Aamir, M., Ahmed, E., Sharif, A., … Iqbal, S. (2014). Synthesis and Characterization of Some Novel 4-Aryloxy Substituted Pyrazoles. Asian Journal of Chemistry, 26(21), 7435–7438. https://doi.org/10.14233/ajchem.2014.17172

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C. Lamberth, Heterocycles, 71, 1467 (2007); doi:10.3987/REV-07-613.

A.M. Farag, A.S. Mayhoub, S.E. Barakat and A.H. Bayomi, Bioorg. Med. Chem., 16, 4569 (2008); doi:10.1016/j.bmc.2008.02.043.

B. Insuasty, A. Tigreros, F. Orozco, J. Quiroga, R. Abonia, M. Nogueras, A. Sanchez and J. Cobo, Bioorg. Med. Chem., 18, 4965 (2010); doi:10.1016/j.bmc.2010.06.013.

A.M. Farag, A.S. Mayhoub, S.E. Barakat and A.H. Bayomi, Bioorg. Med. Chem., 16, 881 (2008); doi:10.1016/j.bmc.2007.10.015.

J. Svete, ARKIVOC, 35 (2006).

I.M. El-Deeb and S.H. Lee, Bioorg. Med. Chem., 18, 3961 (2010); doi:10.1016/j.bmc.2010.04.029.

D. Raffa, G. Daidone, B. Maggio, S. Cascioferro, F. Plescia and D. Schillaci, IL Farmaco, 59, 215 (2004); doi:10.1016/j.farmac.2003.10.004.

S.A.F. Rostom, Bioorg. Med. Chem., 14, 6475 (2006); doi:10.1016/j.bmc.2006.06.020.

K.M. Cheung, T.P. Matthews, K. James, M.G. Rowlands, K.J. Boxall, S.Y. Sharp, A. Maloney, S.M. Roe, C. Prodromou, L.H. Pearl, G.W. Aherne, E. McDonald and P. Workman, Bioorg. Med. Chem. Lett., 15, 3338 (2005); doi:10.1016/j.bmcl.2005.05.046.

B.W. Dymock, X. Barril, P.A. Brough, J.E. Cansfield, A. Massey, E. McDonald, R.E. Hubbard, A. Surgenor, S.D. Roughley, P. Webb, P. Workman, L. Wright and M.J. Drysdale, J. Med. Chem., 48, 4212 (2005); doi:10.1021/jm050355z.

X. Barril, M.C. Beswick, A. Collier, M.J. Drysdale, B.W. Dymock, A. Fink, K. Grant, R. Howes, A.M. Jordan, A. Massey, A. Surgenor, J. Wayne, P. Workman and L. Wright, Bioorg. Med. Chem. Lett., 16, 2543 (2006); doi:10.1016/j.bmcl.2006.01.099.

G.M. Allan, C. Bubert, N. Vicker, A. Smith, H.J. Tutill, A. Purohit, M.J. Reed and B.V.L. Potter, Mol. Cell. Endocrinol., 248, 204 (2006); doi:10.1016/j.mce.2005.10.021.

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D. Kim, Y. Lee, Y.W. Lee, P.M. Dewang, Y.Y. Sheen, Y.W. Kim, H. Park, J. Yoo, H.S. Lee and Y. Kim, Bioorg. Med. Chem., 18, 4459 (2010); doi:10.1016/j.bmc.2010.04.071.

M. Comes Franchini, B.F. Bonini, C.M. Camaggi, D. Gentili, A. Pession, M. Rani and E. Strocchi, Eur. J. Med. Chem., 45, 2024 (2010); doi:10.1016/j.ejmech.2010.01.014.

S.A.F. Rostom, M.A. Shalaby and M.A. El-Demellawy, Eur. J. Med. Chem., 38, 959 (2003); doi:10.1016/j.ejmech.2003.08.003.

M.S.M. Al-Saadi, S.A.F. Rostom and H.M. Faid Allah, Saudi Pharm. J., 13, 89 (2005).

V.K. Aggarwal, J. de Vicente and R.V. Bonnert, J. Org. Chem., 68, 5381 (2003); doi:10.1021/jo0268409.

T. Kawakami, K. Uehata and H. Suzuki, Org. Lett., 2, 413 (2000); doi:10.1021/ol9911167.

R. Olivera, R. SanMartin and E. Domínguez, J. Org. Chem., 65, 7010 (2000); doi:10.1021/jo000609i.

V. Padmavathi, K. Sharmila, A. Balaiah, A.S. Reddy and D.B. Reddy, Synth. Commun., 31, 2119 (2001); doi:10.1081/SCC-100104462.

K. Longhi, D.N. Moreira, M.R.B. Marzari, V.M. Floss, H.G. Bonacorso, N. Zanatta and M.A.P. Martins, Tetrahedron Lett., 51, 3193 (2010); doi:10.1016/j.tetlet.2010.04.038.

L. Pizzuti, L.A. Piovesan, A.F.C. Flores, F.H. Quina and C.M.P. Pereira, Ultrason. Sonochem., 16, 728 (2009); doi:10.1016/j.ultsonch.2009.02.005.

A.B. Khudoyarov, Kh.T. Sharipov, V.G. Yusupov and N.A. Parpiev, Koordinats. Khim., 13, 1113 (1987).

M. Sher, Z. Ahmed, M.A. Rashid, C. Fischer, A. Spannenberg and P. Langer, Tetrahedron, 63, 4929 (2007); doi:10.1016/j.tet.2007.03.143.

K.N. Zelenin, A.R. Tugusheva, S.I. Yakimovich, V.V. Alekseev and E.V. Zerova, Chem. Het. Comp., 38, 668 (2002); doi:10.1023/A:1019909117505.

Issue

Vol. 26 No. 21 (2014): Vol 26 Issue 21

Synthesis and Characterization of Some Novel 4-Aryloxy Substituted Pyrazoles

Corresponding Author(s) : Ejaz Ahmed

Abstract

Keywords

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