Synthesis and photophysical property studies of the 2,6,8-triaryl-4-(phenylethynyl)quinazolines

• Published in: Molecules (Basel, Switzerland) Vol. 19; no. 1; pp. 795 - 818
• Main Authors: Mphahlele, Malose Jack, Paumo, Hugues Kadem, El-Nahas, Ahmed M, El-Hendawy, Morad M
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 10.01.2014; MDPI
• Subjects: 2,6,8-triaryl-4-(phenylethynyl)quinazolines; 2-aryl-6,8-dibromo-4-(alkynyl)quinazolines; 2-aryl-6,8-dibromo-4-chloroquinazolines; 2-aryl-6,8-dibromoquinazolin-4(3H)-ones; Catalysis; Cyclization; Iodine; Iodine - chemistry; Models, Chemical; Oxidation-Reduction; photophysical properties; Quantum Theory; Quinazolines - chemical synthesis; Quinazolines - chemistry; Sonogashira cross-coupling; Spectrometry, Fluorescence; Spectrophotometry, Ultraviolet; Suzuki cross-coupling; Egypt
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules19010795

The 2-aryl-6,8-dibromo-4-chloroquinazolines derived from the 2-aryl-6,8-dibromoquinazolin-4(3H)-ones were subjected to the Sonogashira cross-coupling with terminal acetylenes at room temperature to afford novel 2-aryl-6,8-dibromo-4-(alkynyl)quinazoline derivatives. Further transformation of the 2-aryl-6,8-dibromo-4-(phenylethynyl)quinazolines via Suzuki-Miyaura cross-coupling with arylboronic acids occurred without selectivity to afford the corresponding 2,6,8-triaryl-4-(phenylethynyl)quinazolines. The absorption and emission properties of these polysubstituted quinazolines were also determined.