European Journal of Chemistry

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

Article Sidebar

PDF
Published: Mar 31, 2016
DOI: https://doi.org/10.5155/eurjchem.7.1.128-134.1370
Keywords:
Bis-quinazoline, Triazolo-quinazoline, 4-Chloroquinazolines, Pyrimidino-quinazoline, 4-Hydrazinoquinazoline, 4-Heteroarylquinazoline
Section
Research Article
Issue
Vol. 7 No. 1 (2016): March 2016
Dates
Received 2015-11-22
Accepted 2016-02-06
Published 2016-03-31


Main Article Content

Yaser Abdel-Moemen El-Badry
Organic Chemistry Laboratory, Faculty of Specific Education, Ain Shams University, 11566 Abbasseya, Cairo, Egypt
Ekhlass Nassar
Organic Chemistry Department, Faculty of Women`s for Arts, Science and Education, Ain Shams University, 11767, Cairo, Egypt
Mahr Abdel-Aziz El-Hashash
Organic Chemistry Department, Faculty of Science, Ain Shams University, 11566 Abbasseya, Cairo, Egypt

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.


icon graph This Abstract was viewed 1822 times | icon graph Article PDF downloaded 932 times

How to Cite
(1)
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.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
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

Supporting Agencies

Chemistry Department, Dortmund Technological University, Germany,
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).