European Journal of Chemistry

Synthesis and characterization of some new 4-heteroaryl quinazoline and fused triazolo quinazoline derivatives



Main Article Content

Yaser Abdel-Moemen El-Badry
Ekhlass Nassar
Mahr Abdel-Aziz El-Hashash

Abstract

Treatment of chloroquinazoline (2) with primary amines (2-aminothiazoles and sulpha drugs) and secondary amines (morpholine, piperidine, and piperazine) furnished 4-substituted aminoquinazolines (3a,b and 4a,b), 4-aryl quinazolines (5a,b), and bisquinazoline (6). Hydrazinolysis of compound 2 using hydrazine hydrate, phenyl hydrazine, and sulphonyl hydrazine afforded compound 8 and 9a,b. 1,2,4-Trizolo-quinazoline derivatives (7a-c) were obtained via a one-pot reaction of chloroquinazoline (2), hydrazine hydrate, and aromatic aldehydes. Additionally, 1,2,4-trizolo-quinazoline derivatives (10a,b) were furnished when compound 2 was treated with acid hydrazides like acetyl and benzoyl hydrazides. Pyrimidino quinazoline (13) has been constructed via a three-step conversion of chloroquinazoline 2 using interaction with malononitrile followed by partial hydrolysis and hetero-ring cyclization. All the synthesized compounds were fully characterized using physical and spectral data like, FT-IR, 1H NMR, 13C NMR, and HR-MS.


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El-Badry, Y. A.-M.; Nassar, E.; El-Hashash, M. A.-A. Synthesis and Characterization of Some New 4-Heteroaryl Quinazoline and Fused Triazolo Quinazoline Derivatives. Eur. J. Chem. 2016, 7, 128-134.

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References

[1]. Genady, A. R. Eur. J. Med. Chem. 2009, 44, 409-416.
http://dx.doi.org/10.1016/j.ejmech.2008.02.037

[2]. Alagarsamy, V. Pharmazie 2004, 59, 753-755.

[3]. Grover, G.; Kini, S. G. Eur. J. Med. Chem. 2006, 41, 256-262.
http://dx.doi.org/10.1016/j.ejmech.2005.09.002

[4]. Wada, J. J. U. S. Patent No. 4, 528288, Chem. Abstr. 1986, 104, 5889-5889.

[5]. Alagarsamy, V.; Shankar, D.; Murugesan, S. Biomed. Pharamacoether. 2008, 62, 173-178.
http://dx.doi.org/10.1016/j.biopha.2007.08.025

[6]. He, J.; Wang, X.; Zhao, X.; Liang, Y. J.; He, H.; Fu, L. Eur. J. Med. Chem. 2012, 54, 925-930.
http://dx.doi.org/10.1016/j.ejmech.2012.06.003

[7]. Li, J.; Zhang, Q.; Jia, Z.; Zhou, B.; Cui, N.; Liang, X. PCT Int, Appl. (2013), WO2013170757 A1 20131121.

[8]. Haffner, C. D.; Becherer, J. D. Boros, E. E.; Cadilla, R.; Carpenter, T.; Cowan, D.; Deaton, D. N.; Guo, Y.; Harrington, W.; Henke, B. R. J. Med. Chem. 2015, 58(8), 3548-3571.
http://dx.doi.org/10.1021/jm502009h

[9]. Mott, B. T.; Tanega, C.; Shen, M.; Maloney, D. J.; Shinn, P.; Leister, W.; Marugan, J. J.; Inglese, J.; Austin, C. P.; Mistelli, T. Bioorg. Med. Chem. Let. 2009, 19(23), 6700-6705.
http://dx.doi.org/10.1016/j.bmcl.2009.09.121

[10]. Holladay, M. W.; Setti, E.; U. S. Patent Appl. Publ. (2012), US20120053193 A1 20130301.

[11]. El-Hashash, M. A.; Guirguis, D. B.; El-Badry, Y. A. Der Pharma Chemica 2011, 3(6), 147-159.

[12]. El-Badry, Y. A.; Anter, N. A.; El-Sheshtawy, H. S. Der Pharma Chemica 2012, 4(3), 1361-1370.

[13]. Carson, D. A.; Cottam, H. B.; Howard, B.; Hayashi, T.; Nour, A.; U. S. Pat. Appl. Publ. (2015), US 20150132342 A1 20150514.

[14]. Armstrong, R. C.; Belli, B.; Holladay, M. W.; Rowbottom, M. W.; U. S. Pat. Appl. Publ. (2012), US 20120053176 A1 20120301.

[15]. El-Hashash, M. A.; Abdel-Rahman, T. M.; El-Badry, Y. A. Ind. J. Chem. B 2006, 45, 1470-1477.

[16]. El-Badry, Y. A. Acta Chim. Slov. 2010, 57, 836-841.

[17]. El-Hashash, M. A.; El-Badry, Y. A. Helv. Chim. Acta 2011, 94, 389-396.
http://dx.doi.org/10.1002/hlca.201000230

[18]. El-Badry, Y. A.; El-Farragy, A. F.; Eilbracht, P. Helv. Chim. Acta 2013, 96(9), 1782-1792.
http://dx.doi.org/10.1002/hlca.201200237

[19]. El-Hashash, M. A.; El-Badry, Y. A. J. Adv. Chem. 2013, 4(3), 548-553.

[20]. El-Badry, Y. A.; Anter, N. A.; El-Hashash, M. A. Ind. J. Chem. B 2014, 53, 1574-1583.

[21]. Wolfe, J. F.; Rathman, T. L.; Sleevi, M. C.; Campbell, J. A.; Greenwood, T. D. J. Med. Chem. 1990, 33, 161-166.
http://dx.doi.org/10.1021/jm00163a027

[22]. Hosam, A. S.; Nermen, A. O., Ahmed, H. M. Molecules 2011, 16, 10187-10201.
http://dx.doi.org/10.3390/molecules161210187

[23]. Kundu, S. K.; Mahindaralne, M. P. D.; Quintero, M. V.; Bao, A.; Negrete, G. R. Arkivoc 2008, 2, 33-42.

[24]. Madkour, H. M. F.; Soliman, E. A.; Salem, M. A. I.; El-Bordainy, E. A. A. Bull. Pol. Acad. Sci. 1999, 47, 218-223.

[25]. Almasirad, A.; Vousooghi, N.; Tabatabai, S. A.; Kebriaeezadeh, A.; Shafiee, A. Acta Chim. Solv. 2007, 54, 317-324.

[26]. Alagarsamy, V.; Solomon, V. R.; Murugan, M. Bioorg. Med. Chem. 2007, 15, 4009-4015.
http://dx.doi.org/10.1016/j.bmc.2007.04.001

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