European Journal of Chemistry 2016, 7(1), 128-134 | doi: https://doi.org/10.5155/eurjchem.7.1.128-134.1370 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Yaser Abdel-Moemen El-Badry (1,*) , Ekhlass Nassar (2) , Mahr Abdel-Aziz El-Hashash (3)

(1) Organic Chemistry Laboratory, Faculty of Specific Education, Ain Shams University, 11566 Abbasseya, Cairo, Egypt
(2) Organic Chemistry Department, Faculty of Women`s for Arts, Science and Education, Ain Shams University, 11767, Cairo, Egypt
(3) Organic Chemistry Department, Faculty of Science, Ain Shams University, 11566 Abbasseya, Cairo, Egypt
(*) Corresponding Author

Received: 22 Nov 2015 | Revised: 18 Jan 2016 | Accepted: 06 Feb 2016 | Published: 31 Mar 2016 | Issue Date: March 2016

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.


Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Bis-quinazoline; Triazolo-quinazoline; 4-Chloroquinazolines; Pyrimidino-quinazoline; 4-Hydrazinoquinazoline; 4-Heteroarylquinazoline

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.7.1.128-134.1370

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1188 times | icon graph PDF Article downloaded 572 times

Funding information


Chemistry Department, Dortmund Technological University, Germany,

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


How to cite


El-Badry, Y.; Nassar, E.; El-Hashash, M. Eur. J. Chem. 2016, 7(1), 128-134. doi:10.5155/eurjchem.7.1.128-134.1370
El-Badry, Y.; Nassar, E.; El-Hashash, M. Synthesis and characterization of some new 4-heteroaryl quinazoline and fused triazolo quinazoline derivatives. Eur. J. Chem. 2016, 7(1), 128-134. doi:10.5155/eurjchem.7.1.128-134.1370
El-Badry, Y., Nassar, E., & El-Hashash, M. (2016). Synthesis and characterization of some new 4-heteroaryl quinazoline and fused triazolo quinazoline derivatives. European Journal of Chemistry, 7(1), 128-134. doi:10.5155/eurjchem.7.1.128-134.1370
El-Badry, Yaser, Ekhlass Nassar, & Mahr Abdel-Aziz El-Hashash. "Synthesis and characterization of some new 4-heteroaryl quinazoline and fused triazolo quinazoline derivatives." European Journal of Chemistry [Online], 7.1 (2016): 128-134. Web. 3 Jun. 2023
El-Badry, Yaser, Nassar, Ekhlass, AND El-Hashash, Mahr. "Synthesis and characterization of some new 4-heteroaryl quinazoline and fused triazolo quinazoline derivatives" European Journal of Chemistry [Online], Volume 7 Number 1 (31 March 2016)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.7.1.128-134.1370


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2016, 7(1), 128-134 | doi: https://doi.org/10.5155/eurjchem.7.1.128-134.1370 | Get rights and content

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c)




© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.