Novel π‐Extended Quinazoline‐Ferrocene Conjugates: Synthesis, Structure, and Redox Behavior

European Journal of Organic Chemistry
2020.0

Abstract

Novel ferrocene conjugates of tricyclic quinazoline derivatives are prepared by condensation of active C-6 methylene groups of mackinazolinones with ferrocenecarbaldehyde. Following this route the conjugated parent alkaloid as well as derivatives with nitro, amino, and alkanoylamino groups at C-2 were attached at the ferrocene moiety, thereby significantly extending the delocalized pi system. In addition, the parent compound was subjected to the reaction with ferrocene-1,1'-dicarbaldehyde, giving rise to the symmetrical and unsymmetrical double condensation products - 1,1'-disubstituted ferrocene derivatives, which bear two alkaloid substituents. Some of the compounds obtained were subjected to X-ray crystallographic analyses. The influence of the substituents at C-2 through the extended conjugated pi system on the iron atom is reflected by results of cyclovoltammetric measurements.

Knowledge Graph

Similar Paper

Novel π‐Extended Quinazoline‐Ferrocene Conjugates: Synthesis, Structure, and Redox Behavior
European Journal of Organic Chemistry 2020.0
New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: Synthesis, and in vitro antimalarial activity
Bioorganic & Medicinal Chemistry 2008.0
Synthesis of conjugates of (−)-cytisine derivatives with ferrocene-1-carbaldehyde and their cytotoxicity against HEK293, Jurkat, A549, MCF-7 and SH-SY5Y cells
Tetrahedron 2020.0
New Tricyclic Aryl Quinazoline Derivatives by Suzuki‐Miyaura Cross‐Coupling
ChemistryOpen 2024.0
Synthesis and antimalarial activities of rhenium bioorganometallics based on the 4-aminoquinoline structure
Bioorganic & Medicinal Chemistry 2010.0
Metallocene-based antimalarials: An exploration into the influence of the ferrocenyl moiety on in vitro antimalarial activity in chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum
Bioorganic & Medicinal Chemistry 2007.0
Probing the Role of the Covalent Linkage of Ferrocene into a Chloroquine Template
Journal of Medicinal Chemistry 2006.0
Antileishmanial activity of quinazoline derivatives: Synthesis, docking screens, molecular dynamic simulations and electrochemical studies
European Journal of Medicinal Chemistry 2015.0
New Members of the Cinchona Alkaloids Family: Assembly of the Triazole Heterocycle at the 6′ Position
Molecules 2021.0
Synthesis, characterization, antiparasitic and cytotoxic evaluation of thioureas conjugated to polyamine scaffolds
European Journal of Medicinal Chemistry 2013.0