SYNTHESIS OF NOVEL MONO-SUBSTITUTED “QUINAZOLINE-UREA” HYBRID MOLECULES
Abstract
The main objectives of this study were to identify simple and convenient methods for the synthesis of 6-bromo-2-chloro-4-aminoquinazolines and to carry out their condensation reactions with various isocyanates: o-, m-, and p-tolyl isocyanates. 6-Bromo-2-chloro-4-aminoquinazolines contain an amino group at the position 4, which exhibits nucleophilic character. Isocyanates, in contrast, are strong electrophiles, and amines readily attack their carbonyl carbon atoms. As a result, a nucleophilic condensation reaction occurs, leading to the formation of a urea fragment (–NH–CO–NH–R). The reactions were performed using 6-bromo-2,4-dichloroquinazoline, ammonia, and triethylamine (TEA) in a molar ratio of 1:1.5:1.5. Subsequently, 6-bromo-2-chloro-4-aminoquinazoline and the corresponding isocyanate were reacted in a 1:1 molar ratio for 6 h. The desired compounds were synthesized in good yields: 3 (80%), 4 (75%), 5 (68%), 6 (72%), 7 (79%), 8 (65%), 9 (73%) and 10 (64%). The structures of the synthesized compounds were confirmed by IR spectroscopy, 1H NMR spectroscopy, and mass spectrometry.
References
- Mohammed M. Ghoneim, Mohamed A. Abdelgawad, Nadia A. A. Elkanzi, Della Grace Thomas Parambi, Izzeddin Alsalahat, Amr Farouk, Rania B. Bakr. (2024). A literature review on pharmacological aspects, docking studies, and synthetic approaches of quinazoline and quinazolinone derivatives.Archiv der Pharmazie.[Crossref]
- Sara Masoudinia, Marjaneh Samadizadeh, Maliheh Safavi, Hamid Reza Bijanzadeh, Alireza Foroumadi. (2024). Novel quinazolines bearing 1,3,4-thiadiazole-aryl urea derivative as anticancer agents: design, synthesis, molecular docking, DFT and bioactivity evaluations.BMC Chemistry.[Crossref]
Publication Details
This article is licensed under a Creative Commons Attribution 4.0 International License.