Synthesis of some new heterocyclic compounds derived from 4-(4-hydroxy-3-chlorophenyl) azoaceto phenone


Farouq E. Hawaiz1, Mohammed K1. Samad and Marlin Y. Aziz1

1College of Education/ University of Salahaddin-Hawler, Arbil, Kurdistan Region, Iraq



Abstract
p-Aminoacetophenone underwent diazotization and coupling reaction with 2-
chlorophenol to give a starting material 4-(4-hydroxy-3-chlorophenyl)azoacetophenone.
The prepared starting material was benzylated with benzylbromide producing 4-[4-
benzyloxy-3-chloro-phenyl]azoacetophenone. The later has been reacted with different
substituted benzaldehydes affording a series of new chalcones. The newly synthesized
chalcones were treated with hydrazine hydrate to form the desired molecules azobenzyloxy-pyrazoline derivatives. The spectrum measurements of FT-IR,
1H-NMR and
13C-NMR, confirmed the expected structures of the newly synthesized compounds. 

Key Words: p-aminoacetophenone, diazotization, coupling reaction, azo-chalcones, azo-pyrazoline 



References
[1] Farouq E. H., Lana H. Ch., and Diler D. G., "Solvent- Free Synthesis and Spectroscopic Identification of
Some Chalcones and Imines Derived From p-Amino acetophenone" Tikrit Journal of Pure science. 15(2);
78-86, (2010).

[2] Bhaskar S. D., Santosh S. C. Gajanan G. M. and Baseer M. S., "An efficient and rapid synthesis of some
novel 1,3-diaryl, diazenyl, 2-propen-1-one using PEG- 400 as recyclable solvent and their in vitro
antimicrobial evaluation" Orbital Elec. J. Chem., Campo Grande, 4(1); 7-15, (2012).

[3] Awaz J. H., and Hashim J. A., "Synthesis and spectroscopic characterization of some new azo-
thiazolidinone derivatives” Der Chemica Sinica., 2(5); 136–146, (2011).

[4] Mohame J. E., and Hussniyia A., "Synthesis of some compounds derived from chalcones" Sci. Revs.
Chem. Commun., 2(2), 103-107, (2012).
[5] Jorge T., Efraín P. Jairo Q., Justo C., and Manuel N. "Ultrasonics Promoted Synthesis of
5-(Pyrazol-4-yl)-4,5-Dihydropyrazoles Derivatives" Appl. Sci., 3, 457-468, (2011).
[6] Sherif A. F. R., Mona H. B., Heba A. A. El R., Hayam M.A. A. and Abeer E. A.W.,
"Synthesis of Some Pyrazolines and Pyrimidines Derived from Polymethoxy Chalcones as Anticancer and
Antimicrobial Agents", Arch. Pharm. Chem. Life Sci., 344, 572–587,(2011).
[7] Yordanka B. I., Georgi T. M. and Ognyan I. P., "New heterocyclic chalcones. Part 6. Synthesis
and cytotoxic activities of 5- or 6-(3-aryl- 2-propenoyl)-2(3 H)-benzoxazolones", Heterocycl.
Commun.,19 (1); 23–28,(2013).
[8] Chinnalalaiah R., Pavani B., Deepthi G.J., Sharma JVC and Vykuntam U., "Synthesis, Characteization
and Analgesic Activity of Isoxazole and Pyrazole derivatives". J Pharm Biol Sci, 1(1); 8-11,(2013).
[9] Rahaman S.A., Prasad Y.R., Bhuvaneswari K., Kumar P., "Synthesis and antihistaminic activity of novel
pyrazole derivatives" International Journal of ChemTech Research. 2(1); 16-20, (2010).
[10] Nadia A. K., Eman M. A., Hala B. El-N., Osama K. A., and Ahmed M. A. A., "Synthesis and
Biological Evaluation of Novel Pyrazoline Derivatives as Anti-inflammatory and Antioxidant Agents", Arch
Pharm Res., 5(6); 995-1002, (2012).
[11] Seham Y. H., "Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole
Derivatives" Molecules, 18, 2683-2711, (2013).
[12] Vishal D. J., Mahendra D. K., Sarita S., "Synthesis and Antimicrobial activities of Various Pyrazolines
from Chalcones", International Journal of ChemTech Research, 4, 3, 971-975, (2012).
[13] Uhood J. Al-H., Tarik E. G., Howra H. R., "Synthesis and Characterization of Azo Compounds and
Study of the Effect of Substituents on Their Liquid Crystalline Behavior", Molecules, 15, 5620-5628(2010).
[14] Farouq E. H., Awaz J. H., Mohammed K. S., "One‐pot three‐component synthesis of some new azo‐
pyrazoline derivatives" European J Chem., 5(2); 233‐236, (2014).
[15] Nadia A. K., Eman M. A., Hala B. El-N., Osama K. A., Ahmed M. Al-A. "Synthesis and Biological
Evaluation of Novel 6-(3-(4-Dihydro-1,5-diphenyl-1H-pyrazol-3-yl)phenylamino(Pyridazin-3(2H)-one
Derivatives" International Journal of Organic Chemistry, 2, 371-376, (2012).
[16] Farouq, E.H., Mohammad, K. S., "Synthesis and Spectroscopic Characterization of Some New
Biological Active Azo–Pyrazoline Derivatives" E-Journal of Chemistry, 9(3), 1613-1622, (2014).
[17] Field L. D, Stern hell S. and Kalman J. R.. "Organic Structures from Spectra" 3rd addition, John Wiley
and Sons, pp64-68, (2005).
[18] Varun A., Pragi A. and Lamba H. S., "Synthesis and evaluation of chalcone derivatives of 2-acetyl
naphthalene for antifungal and antibacterial activity " Der Pharmacia Lettre, 4 (2); 554-557, (2012).
[19] Ramalingam S., Kannan T., Perumal M., Ganesamoorthy T., "Eco-friendly synthesis and antimicrobial
activities of some 1-phenyl-3(5-bromothiophen-2-yl)-5-(substituted phenyl)-2-pyrazolines" Organic and
Medicinal Chemistry Letters, 2, 2, 1-13, (2012).
[20] Faiq H.S. H., Farouq E. H., Hashim J. A., "Synthesis and characterization of some new pyrazoline
derivatives derived from 2,4-dihydroxybenzaldehyde" International Journal of Chemical and Environmental