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

Malose Jack Mphahlele; Hugues Kadem Paumo; Ahmed M El-Nahas; Morad M El-Hendawy

doi:10.3390/molecules19010795

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

Molecules. 2014 Jan 10;19(1):795-818. doi: 10.3390/molecules19010795.

Authors

Malose Jack Mphahlele¹, Hugues Kadem Paumo², Ahmed M El-Nahas³, Morad M El-Hendawy⁴

Affiliations

¹ Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa. mphahmj@unisa.ac.za.
² Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa. tkademph@unisa.ac.za.
³ Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa. amelnahas@hotmail.com.
⁴ Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa. Morad.elhendawy@yahoo.com.

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyclization
Iodine / chemistry
Models, Chemical
Oxidation-Reduction
Quantum Theory
Quinazolines / chemical synthesis*
Quinazolines / chemistry
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet

Substances

Quinazolines
Iodine