Synthesis and Photophysical Properties ofPolycarbo-Substituted Quinazolines Derived from the2-Aryl-4-chloro-6-iodoquinazolines

Molecules

Lydia Rhyman¹  Ponnadurai Ramasami¹  Malose Jack Mphahlele²  Hugues Kamdem Paumo² 

[1] Computational Chemistry Group, Department of Chemistry, Faculty of Science,University of Mauritius, Réduit 80837, Mauritius;Department of Chemistry, College of Science, Engineering and Technology,University of South Africa, P.O. Box 392, Pretoria 0003, South Africa;

关键词: 2-aryl-4-chloro-8-iodoquinazolines;    cross-coupling reactions;    polycarbo-substituted quinazolines;    photophysical properties;   

DOI  :  10.3390/molecules200814656

来源: DOAJ

【 摘 要 】

The reactivity of the 2-aryl-4-chloro-6-iodoquinazolines towards palladium catalyzed sequential (Sonogashira/Suzuki-Miyaura) and one-pot two-step cross-coupling(bis-Sonogashira, and successive Sonogashira/Stille) reactions to afford novel unsymmetrical polycarbo-substituted quinazolines has been evaluated. In contrast to the chloro-bromo substituted quinazolines in which selectivity has been previously found to generally favor substitution at the more activated C(4)-Cl bond over the weaker Csp2-Br bond, substitution in the case of the chloro-iodo derivatives favors cross-coupling through the intrinsically more reactive Csp2-I bond. The electronic absorption and emission properties of the prepared2,3-diaryl-6-(phenylethynyl)quinazolines were studied in solvents of different polarity (dichloromethane, toluene, DMF, methanol) and CH2Cl2-TFA mixture using UV-Vis and emission spectroscopic techniques complemented with density functional theory method to establish the effect of substituents on intramolecular charge transfer properties.

【 授权许可】

Unknown