European Journal of Chemistry 2014, 5(2), 233-236 | doi: https://doi.org/10.5155/eurjchem.5.2.233-236.979 | Get rights and content

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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 | 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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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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Funding information


Chemistry Department, College of Education, Salahaddin University, Hawler, Erbil, Iraq

Citations

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[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
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[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
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[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
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[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
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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. 4 Jul. 2022
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)

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