

One-pot three-component synthesis of some new azo-pyrazoline derivatives
Farouq Emam Hawaiz (1,*)



(1) Department of Chemistry, College of Education, University of Salahaddin-Hawler, Erbil 44001, Kurdistan Region, Iraq
(2) Department of Chemistry, College of Education, University of Salahaddin-Hawler, Erbil 44001, Kurdistan Region, Iraq
(3) Department of Chemistry, College of Education, University of Salahaddin-Hawler, Erbil 44001, Kurdistan Region, Iraq
(*) Corresponding Author
Received: 30 Nov 2013 | Revised: 05 Jan 2014 | Accepted: 06 Jan 2014 | Published: 30 Jun 2014 | Issue Date: June 2014
Abstract
The starting material azo-benzyloxy acetophenone (2) has been synthesized in three steps; the direct diazotization of p-aminoacetophenone and its coupling reaction with m-cresol gave azo-acetophenone (1), which was benzylated with p-chlorobenzylchloride to give the starting material (2). The later compound was subjected to the one-pot three-component condensation reaction with substituted benzaldehydes and phenylhydrazine in the presence of sodium hydroxide to afford the target molecule azo-pyrazoline derivatives (3a-e) in high yields and short reaction times. The structures of the synthesized compounds were elucidated by using FT-IR, 1H NMR, 13C NMR and 13C DEPT 135 spectra.
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European Journal of Chemistry
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DOI: 10.5155/eurjchem.5.2.233-236.979
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Chemistry Department, College of Education, Salahaddin University, Hawler, Erbil, Iraq
Citations
[1]. Katharigatta N. Venugopala, Mohammed Habeebuddin, Bandar E. Aldhubiab, Afzal Haq Asif
Design, Synthesis, and In Vitro Evaluation of Novel Indolyl DiHydropyrazole Derivatives as Potential Anticancer Agents
Molecules 26(17), 5235, 2021
DOI: 10.3390/molecules26175235

[2]. Adel Zamri, Hilwan Y. Teruna, Sri Wulansari, Noval Herfindo, Neni Frimayanti, Ihsan Ikhtiarudin
3-(3,4-Dimethoxyphenyl)-5-(2-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole
Molbank 2019(4), M1088, 2019
DOI: 10.3390/M1088

[3]. Saba Farooq, Zainab Ngaini
One-Pot and Two-Pot Synthesis of Chalcone Based Mono and Bis-Pyrazolines
Tetrahedron Letters 61(4), 151416, 2020
DOI: 10.1016/j.tetlet.2019.151416

[4]. Jasril Jasril, Neni Frimayanti, Yuana Nurulita, Adel Zamri, Ihsan Ikhtiarudin, Guntur Guntur
5-(4-Fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole
Molbank 2021(1), M1197, 2021
DOI: 10.3390/M1197

[5]. Mohammed Kareem Samad, Farouq Emam Hawaiz
Synthesis, characterization, antioxidant power and acute toxicity of some new azo-benzamide and azo-imidazolone derivatives with in vivo and in vitro antimicrobial evaluation
Bioorganic Chemistry 85, 431, 2019
DOI: 10.1016/j.bioorg.2019.01.014

References
[1]. Hassan, V.; Ashraf, F. Molecules 2010, 15, 2972-2979.
http://dx.doi.org/10.3390/molecules15129008
[2]. Valentina, M.; Matthew, M. H.; Long, M.; Christine, M. C.; Andreas, P. T.; Dean, M. W. Synthesis 2002, 12, 1669-1674.
[3]. Santhosh, P.; Rajeswar, R. V. Org. Commun. 2012, 5(3), 143-149.
[4]. Mohammad, A.; Nasim, S.; Motahareh, H. Arkivoc 2012, 9, 13-20.
[5]. Hamad, M.; Khaled, D. K.; Aisha, Y. A.; Mohamed, H. E. Molecules 2010, 15, 6619-6629.
http://dx.doi.org/10.3390/molecules15096619
[6]. Javad, A.; Masoud, S.; Farhad, H.; Reza, M. Arkivoc 2006, 11, 47-58.
[7]. Mohammed, R. A.; Mohammed, H. R. K.; Vedula, G. S.; Nasreen, B.; Syed, A.; Yejella, R. P. Eur. J. Chem. 2012, 3(2), 186‐190.
http://dx.doi.org/10.5155/eurjchem.3.2.186-190.554
[8]. Bharat, K.; Vishal, P.; Sushma, R.; Ravi, K.; Tiwari, I. C. Int. J. Chem. Res. 2010, 2(1), 25-27.
[9]. Alam, M. M.; Marella, A.; Akhtar, M.; Husain, A.; Yar, M.; Shaquiquzzaman, M.; Tanwar, O. P.; Saha, R.; Khanna, S.; Shafi, S. Acta Pol. Pharm. 2013, 70(3), 435-441.
[10]. Lei-Lei, W.; Yi-Cen, G.; Ting, H.; Lei, Z.; Xing-Li, F.; Hai-Yan, F.; Hua, C.; Rui-Xiang, L. Synthesis 2012, 1577-1583.
[11]. Li, R.; Kenyon, G. L.; Cohen, F. E. J. Med. Chem. 1995, 38, 5031-5036.
http://dx.doi.org/10.1021/jm00026a010
[12]. Prasad, Y. R.; Kumar, P. P.; Kumar, P. R.; Rao, A. S. E-J. Chem. 2008, 5(1), 144-148.
[13]. Kouskoura, M.; Hadjipavlou, L. D.; Giakoumakou M. Med. Chem. 2008, 4, 586-596.
http://dx.doi.org/10.2174/157340608786242070
[14]. Sahu, S. K.; Banerjee, M.; Samantray, A.; Behera, A.; Azam, M. A. Trop. J. Pharm. Res. 2008, 7(2), 961-968.
http://dx.doi.org/10.4314/tjpr.v7i2.14664
[15]. Anees, A.; Siddiqui, M. D.; Azizur, R.; Shaharyar, M.; Ravinesh M. Chem. Sci. J. 2010, 8, 1-10.
[16]. Suthakaran, R.; Somasekhar, G.; Sredivi, C. H.; Marikannan, K. S.; Nagarajan, G. Asian J. Chem. 2007, 19(5), 3353-3362.
[17]. Ahmet, O.; Gulhan, T.; Zafer A. K. Turk. J. Chem. 2008, 32, 529-538.
[18]. Chovatla, Y. S.; Gandhi, S. P.; Gorde, P. L.; Bagade, S. B. Orient. J. Chem. 2010, 26(1), 275-278.
[19]. Ngaini, Z.; Haris, S. M.; Hussain, H.; Kamaruddin, K. World J. Chem. 2009, 4(1), 9-14.
[20]. Uhood, J.; Tarik, E. G.; Howraa, H. R. Molecules 2010, 15, 5620-5628
http://dx.doi.org/10.3390/molecules15085620
[21]. Veena, V. K.; Vijaya, K. D.; Venkata, R. C. Der Pharma Chem. 2012, 4(5), 2003-2008.
[22]. Farouq, E. H.; Mohammad, K. S. E-J. Chem. 2012, 9(3), 1613-1622.
[23]. Field, L. D.; Stern, S.; Kalman, J. R. Organic Structures from Spectra, 3rd ed.; Wiley & Sons: New York, 2005.
[24]. Assia, S.; Nouara Z.; Ouafa, D.; Mahieddine, M.; Kaddou, L. Eur. J. Chem. 2013, 4(3), 268‐271.
http://dx.doi.org/10.5155/eurjchem.4.3.268-271.824
[25]. Mamta, R.; Mohamad Y. Eur. J. Chem. 2012, 3(1), 21‐25.
http://dx.doi.org/10.5155/eurjchem.3.1.21-25.472
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DOI Link: https://doi.org/10.5155/eurjchem.5.2.233-236.979

















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