Synthesis of pyrazoline derivatives from the 1,3-dipolar cycloadditions using α,β-unsaturated cyclohexanone derivatives

Nouara Ziani; Kaddour Lamara; Assia Sid; Quentin Willem; Benjamin Dassonneville; Albert Demonceau

doi:10.5155/eurjchem.4.2.176-179.757

PDF

Published: Jun 30, 2013

DOI: https://doi.org/10.5155/eurjchem.4.2.176-179.757

Keywords:

Acetic acid, Pyrazolines, Spectroscopy, Hydrazine hydrate, 1, 3-Dipolar cycloadditions, α, β-Unsaturated cyclohexanone derivatives

Section

Research Article

Issue

Vol. 4 No. 2 (2013): June 2013

Dates

Received 2013-02-21
Accepted 2013-04-05
Published 2013-06-30

Nouara Ziani

Département de Chimie, Faculté des Sciences, Université Ferhat Abbas, Sétif, 19000, Algérie

Kaddour Lamara

Laboratory of Applied Chemistry and Materials Technology, Chemistry Institute, University Larbi Ben M’hidi of Oum El Bouaghi, Rue de Constantine, 04000, Algeria

Assia Sid

Laboratory of Applied Chemistry and Materials Technology, Chemistry Institute, University Larbi Ben M’hidi of Oum El Bouaghi, Rue de Constantine, 04000, Algeria

Quentin Willem

Laboratoire de Chimie Macromoléculaire et de Catalyse Organique, Département de Chimie, Université de Liège, Sart-Tilman (B.6a), B-4000 Liège, Belgique

Benjamin Dassonneville

Laboratoire de Chimie Macromoléculaire et de Catalyse Organique, Département de Chimie, Université de Liège, Sart-Tilman (B.6a), B-4000 Liège, Belgique

Albert Demonceau

Laboratoire de Chimie Macromoléculaire et de Catalyse Organique, Département de Chimie, Université de Liège, Sart-Tilman (B.6a), B-4000 Liège, Belgique

Abstract

A series of 2-pyrazolines (3a-d) were obtained by reaction 1,3-dipolar cycloadditions of α,β-unsaturated cyclohexanone derivatives (2a-c) with hydrazine hydrate and 4-nitrophenylhydrazine in the presence of acetic acid and ethanol as solvents. The structures of the synthesized compounds were confirmed by spectroscopic methods; IR, ¹H and ¹³C NMR.

This Abstract was viewed 2430 times |

Article PDF downloaded 1721 times

How to Cite

(1)

Ziani, N.; Lamara, K.; Sid, A.; Willem, Q.; Dassonneville, B.; Demonceau, A. Synthesis of Pyrazoline Derivatives from the 1,3-Dipolar Cycloadditions Using α,β-Unsaturated Cyclohexanone Derivatives. Eur. J. Chem. 2013, 4, 176-179.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Behr, L. C.; Fusco, F.; Jarboe, C. H. In Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, Wiley, R. H. Ed. The Chemistry of Heterocyclic compounds; Wiley-Interscience: New York, NY, 1967.

[2]. Bansal, E.; Srivastava, V. K.; Kumar, A. Eur. J. Med. Chem. 2001, 36, 81-92.
http://dx.doi.org/10.1016/S0223-5234(00)01179-X

[3]. Kumar, A.; A.; Archana; Sharma, S.; Malik, N.; Sharma, P.; Kaushik, K.; Saxena, K. K.; Srivastava, V. K.; Verma, R. S.; Sharma, H.; Gupta, S. C.; Gupta, V.; Agarwal, R. C. Indian J. Chem. B 2004, 43, 1532-1536.

[4]. Barsoum, F. F.; Hosni, H. M.; Girgis, A. S. Bioorg. Med. Chem. 2006, 14, 3929-3927.
http://dx.doi.org/10.1016/j.bmc.2006.01.042
PMid:16460945

[5]. Palaska, E.; Aytemir, M.; Uzbay, I. T.; Erol, D. Eur. J. Med. Chem. 2001, 36, 539-543.
http://dx.doi.org/10.1016/S0223-5234(01)01243-0

[6]. Prasad, Y. R.; Rao, A. L.; Prasoona, L.; Murali, K.; Kumar, P. R. Bioorg. Med. Chem. Lett. 2005, 15, 5030-5034.
http://dx.doi.org/10.1016/j.bmcl.2005.08.040
PMid:16168645

[7]. Souza, F. R.; Souza, V. T.; Ratzlaff, V.; Borges, L. P.; Oliveira, M. R.; Bonacorso, H. G.; Zanatta, N.; Martins, M. A. P.; Mello, C. F. Eur. J. Pharmacol. 2002, 451, 141-147.
http://dx.doi.org/10.1016/S0014-2999(02)02225-2

[8]. Safak, C.; Sarac, S.; Balkan, A.; Ertan, M.; Yulug, N. Hacettepe Univ. Eczacilik Fak. Derg. 1990, 10, 39-49.

[9]. Patel, P.; Koregaokar, S.; Shah, M.; Parekh, H. Farmaco 1996, 51, 59-63.
PMid:8721763

[10]. Grant, N.; Mishriky, N.; Asaad, F. M.; Fawzy, N. G. Pharmazie 1998, 53, 543-547.
PMid:9741063

[11]. Nauduri, D.; Reddy, G. B. S. Chem. Pharm. Bull. 1998, 46, 1254-1260.
http://dx.doi.org/10.1248/cpb.46.1254

[12]. Holla, B. S.; Akberali, P. M.; Shivananda, M. K. Il Farmaco 2000, 55, 256-263.
http://dx.doi.org/10.1016/S0014-827X(00)00030-6

[13]. Solankee, A.; Thakor, I. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2006, 45, 517-522.

[14]. Tiwari, N.; Dwivedi, B.; Nizamuddin, N. Boll. Chim. Farm. 1989, 128, 332-335.
PMid:2637751

[15]. Nimavat, K. S.; Popat, K. H.; Joshi, H. S. Indian J. Heterocycl. Chem. 2003, 12, 225-228.

[16]. Elguero, J. In Comprehensive Heterocyclic Chemistry, Katritzky, A.; Rees, C.; Potts, D.; Eds.; Pergamon, Oxford, UK, 1984, Vol. 5, pp. 167.
http://dx.doi.org/10.1016/B978-008096519-2.00072-2

[17]. Van Auken, T. V.; Rinehart, K. L. Jr. J. Am. Chem. Soc. 1962, 84, 3736-3743.
http://dx.doi.org/10.1021/ja00878a028

[18]. McGreer, D. E.; Morris, P.; Carmichael, G. Can. J. Chem. 1963, 41, 726-731.
http://dx.doi.org/10.1139/v63-103

[19]. Fieser, M.; Fieser, L. F. Reagents for Organic Synthesis, Wiley-Interscience, New York, NY. 1969, Vol. 2, pp. 211.

[20]. Freeman, J. P. J. Org. Chem. 1964, 29, 1379-1382.
http://dx.doi.org/10.1021/jo01029a027

[21]. Nakamichi, N.; Kawashita, Y.; Hayashi, M. Org. Lett. 2002, 4, 3955-3957.
http://dx.doi.org/10.1021/ol0268135
PMid:12599501

[22]. Nakamichi, N.; Kawashita, Y.; Hayashi, M. Synthesis 2004, 1015-1020.

[23]. Zolfigol, M. A.; Azarifar, D.; Mallakpour, S.; Mohammadpoor-Baltork, I.; Forghaniha, A.; Maleki, B.; Abdollahi-Alibeik, M. Tetrahedron Lett. 2006, 47, 833-836.
http://dx.doi.org/10.1016/j.tetlet.2005.11.088

[24]. Robinson, T. P.; Ehlers, T.; Hubbard, R. B.; Bai, X.; Arbiser, J. L.; Goldsmith, D. J.; Bowena, J. P. Bioorg. Med. Chem. Lett. 2003, 13, 115-117.
http://dx.doi.org/10.1016/S0960-894X(02)00832-6

[25]. Robinson, T. P.; Hubbard, R. B.; Ehlers, T. J.; Arbiser, J. L.; Goldsmith, D. J.; Bowena, J. P. Bioorg. Med. Chem. 2005, 13, 4007-4013.
http://dx.doi.org/10.1016/j.bmc.2005.03.054
PMid:15911313

[26]. Dimmock, J. R.; Padmanilayam, M. P.; Zello, G. A.; Nienaber, K. H.; Allen, T. M.; Santos, C. L.; De Clercq, E.; Balzarini, J.; Manavathu, E. K.; Stables, J. P. Eur. J. Med. Chem. 2003, 38, 169-177.
http://dx.doi.org/10.1016/S0223-5234(02)01444-7

[27]. Modzelewska, A.; Pettit, C.; Achanta, G.; Davidson, N. E.; Huang, P.; Khan, S. R. Bioorg. Med. Chem. 2006, 14, 3491-3495.
http://dx.doi.org/10.1016/j.bmc.2006.01.003
PMid:16434201

[28]. Piantadosi, C.; Hall, I. H.; Irvine, J. L.; Carlson, G. L. J. Med. Chem. 1973, 16, 770-795.
http://dx.doi.org/10.1021/jm00265a006

[29]. Ogawa, M.; Ishii, Y.; Nakano, T.; Irifune, S. Jpn. Kohai Tokyo JP. 1988, 63238034 A2.

[30]. Gangadhara, K. K. Polymer. 1995, 36, 1903-1910.
http://dx.doi.org/10.1016/0032-3861(95)90938-X

[31]. Mogilaiah, K.; Reddy, N. V. Synth. Commun. 2003, 33, 73-78.
http://dx.doi.org/10.1081/SCC-120015561

[32]. Hatsuda, M.; Kuroda, T.; Seki, M. Synth. Commun. 2003, 33, 427-434.
http://dx.doi.org/10.1081/SCC-120015773

[33]. Sensfuss, U. Tetrahedron let. 2003, 44, 2371-2374.

[34]. Kreher, U. P.; Rosamilia, A. E.; Raston, C. L.; Scott, J. L.; Strauss, C. R. Org. Lett. 2003, 5, 3107-3110.
http://dx.doi.org/10.1021/ol0351145
PMid:12916993

[35]. Zhang, Z.; Dong, Y. W.; Wang, G. W. Chem. Lett. 2003, 32, 966-967.
http://dx.doi.org/10.1246/cl.2003.966

[36]. Choudary, B. M.; Kantam, M. L.; Ranganath K. V. S.; Mahendar, K.; Sreedher, B. J. Am. Chem. Soc. 2004, 126, 3396-3397.
http://dx.doi.org/10.1021/ja038954n
PMid:15025446

[37]. Sabitha, G.; Reddy, G. S. K. K.; Reddy, K. B.; Yadav, J. S. Synthesis 2004, 263-266.
http://dx.doi.org/10.1055/s-2004-815920

[38]. Husson, J.; Migianu, E.; Beley, M.; Kirsch, G. Synthesis 2004, 267-270.

[39]. Climent, M. J.; Corma, A.; Iborra, S.; Velty, A. J. Catal. 2004, 221, 474-482.
http://dx.doi.org/10.1016/j.jcat.2003.09.012

[40]. Kok, W. L.; Chau, L. T.; Choi, Y. L.; Ahmad, S. M.; Basyaruddin, A, R.; Daud, A. I.; Nordin, H. L. Med. Chem. Res. 2012, 21, 333-344.

[41]. Ziani, N.; Sid, A.; Demonceau, A.; Willem, Q.; Dassonneville, B.; Lamara, K. Eur. J. Chem. 2013, 4(2), 146-148.
http://dx.doi.org/10.5155/eurjchem.4.2.146-148.756

[42]. Wang, L.; Sheng, J.; Tian, H.; Han, J.; Fan, Z.; Qian, C. Synthesis 2004, 3060-3064.
http://dx.doi.org/10.1055/s-2004-834900

[43]. Sid, A.; Lamara, K.; Mokhtari, M.; Ziani, N.; Mosset, P. Eur. J. Chem. 2011, 2(3), 311-313.
http://dx.doi.org/10.5155/eurjchem.2.3.311-313.414

Supporting Agencies

Laboratory of Applied Chemistry and Materials Technology, Chemistry Institute, University Larbi Ben M’hidi of Oum El Bouaghi, Rue de Constantine, 04000, Algeria.

Most read articles by the same author(s)

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics