European Journal of Chemistry 2014, 5(2), 233-236. doi:10.5155/eurjchem.5.2.233-236.979

One-pot three-component synthesis of some new azo-pyrazoline derivatives


Farouq Emam Hawaiz (1,*) , Awaz Jamil Hussein (2) , Mohammed Kareem Samad (3)

(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, Accepted: 06 Jan 2014, Published: 30 Jun 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.



Keywords


Cyclization; Benzylation; Diazotization; Azo-pyrazoline; One-pot synthesis; Azo-acetophenone

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DOI: 10.5155/eurjchem.5.2.233-236.979

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[1]. 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
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DOI: 10.3390/M1088
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[2]. 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
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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


How to cite


Hawaiz, F.; Hussein, A.; Samad, M. Eur. J. Chem. 2014, 5(2), 233-236. doi:10.5155/eurjchem.5.2.233-236.979
Hawaiz, F.; Hussein, A.; Samad, M. One-pot three-component synthesis of some new azo-pyrazoline derivatives. Eur. J. Chem. 2014, 5(2), 233-236. doi:10.5155/eurjchem.5.2.233-236.979
Hawaiz, F., Hussein, A., & Samad, M. (2014). One-pot three-component synthesis of some new azo-pyrazoline derivatives. European Journal of Chemistry, 5(2), 233-236. doi:10.5155/eurjchem.5.2.233-236.979
Hawaiz, Farouq, Awaz Jamil Hussein, & Mohammed Kareem Samad. "One-pot three-component synthesis of some new azo-pyrazoline derivatives." European Journal of Chemistry [Online], 5.2 (2014): 233-236. Web. 14 Nov. 2019
Hawaiz, Farouq, Hussein, Awaz, AND Samad, Mohammed. "One-pot three-component synthesis of some new azo-pyrazoline derivatives" European Journal of Chemistry [Online], Volume 5 Number 2 (30 June 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.2.233-236.979

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