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Molecules 2015, 20(8), 14656-14683; doi:10.3390/molecules200814656

Synthesis and Photophysical Properties of Polycarbo-Substituted Quinazolines Derived from the 2-Aryl-4-chloro-6-iodoquinazolines

1
Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa
2
Computational Chemistry Group, Department of Chemistry, Faculty of Science, University of Mauritius, Réduit 80837, Mauritius
*
Author to whom correspondence should be addressed.
Academic Editor: Philippe Belmont
Received: 3 July 2015 / Revised: 3 August 2015 / Accepted: 7 August 2015 / Published: 13 August 2015
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

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 prepared 2,3-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. View Full-Text
Keywords: 2-aryl-4-chloro-8-iodoquinazolines; cross-coupling reactions; polycarbo-substituted quinazolines; photophysical properties 2-aryl-4-chloro-8-iodoquinazolines; cross-coupling reactions; polycarbo-substituted quinazolines; photophysical properties
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Mphahlele, M.J.; Paumo, H.K.; Rhyman, L.; Ramasami, P. Synthesis and Photophysical Properties of Polycarbo-Substituted Quinazolines Derived from the 2-Aryl-4-chloro-6-iodoquinazolines. Molecules 2015, 20, 14656-14683.

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