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

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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.


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Keywords


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

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DOI: 10.5155/eurjchem.7.1.128-134.1370

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Funding information


Chemistry Department, Dortmund Technological University, Germany,

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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. 28 Nov. 2022
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)

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


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