European Journal of Chemistry

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

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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 2015-12-20
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.


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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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