Abstract
Halogenated quinazolinones and quinazolines are versatile synthetic intermediates for the metal-catalyzed carbon–carbon bond formation reactions such as the Kumada, Stille, Negishi, Sonogashira, Suzuki-Miyaura and Heck cross-coupling reactions or carbon-heteroatom bond formation via the Buchwald-Hartwig cross-coupling to yield novel polysubstituted derivatives. This review presents an overview of the application of these methods on halogenated quinazolin-4-ones and their quinazolines to generate novel polysubstituted derivatives.
Highlights
Introduction and ScopeIn recent years, the development of strategies to efficiently functionalize presynthesized halogenated quinazolinones and quinazolines or their tosylate derivatives via metal-catalyzed cross-coupling reactions to afford novel polycarbo- or polyheteroatom-substituted derivatives with potential application in pharmaceuticals and materials has attracted considerable interest
Lapatinib 3, a 6-heteroaryl substituted 4-anilinoquinazoline derivative is an oral dual tyrosine kinase inhibitor (TKI) that targets both epidermal growth factor receptor (EGFR) and HER2 to inhibit the proliferation of breast cancer cells [3]
These poor yields indicate that the 4-chloroquinazoline moiety is preferred over the 4-bromo- or 4-iodoquinazoline framework in the cross-coupling reactions
Summary
The development of strategies to efficiently functionalize presynthesized halogenated quinazolinones and quinazolines or their tosylate derivatives via metal-catalyzed cross-coupling reactions to afford novel polycarbo- or polyheteroatom-substituted derivatives with potential application in pharmaceuticals and materials has attracted considerable interest. New findings on the biological and photophysical properties of polycarbo-substituted quinazolinones and quinazolines reveal a need to increase the diversity of substituents around these heterocyclic scaffolds To this end, halogenated quinazolinones and quinazoline derivatives have established themselves as important intermediates for the synthesis of polycarbo- and polyheteroatom-substituted derivatives with potential application in material and medicinal chemistry. Most of the review articles in the literature on quinazolinones and quinazolines, on the other hand, only focus on the conventional and microwave syntheses of heteroatom-substituted derivatives as well as their medicinal applications [10,11,12] This prompted us to compile a comprehensive review on the application of the Kumada, Stille, Negishi, Sonogashira, Suzuki-Miyaura and Heck cross-coupling as well as the Buchwald-Hartwig cross-coupling and palladium-catalysed cyanation in the synthesis of polycarbo- or polyheteroatom-substituted quinazolinones and quinazolines derivatives from the corresponding halogenated precursors
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