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

• Published in: European journal of organic chemistry Vol. 2020; no. 23; pp. 3430 - 3440
• Main Authors: Elmuradov, Burkhon, Dräger, Gerald, Butenschön, Holger
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 23.06.2020; Wiley Subscription Services, Inc
• Subjects: Alkaloids; Chemistry; Chemistry, Organic; Condensates; Conjugates; Crystallography; Derivatives; Extended π systems; Ferocenophane; Ferrocene; Physical Sciences; Sandwich complexes; Science & Technology; CRYSTAL-STRUCTURE; MACKINAZOLINONE; COMPLEXES; DEOXYVASICINONE; LUOTONIN-A; Ferrocene; Extended pi systems; Alkaloids; IN-VITRO; Sandwich complexes; BIOORGANOMETALLIC CHEMISTRY; AMINO-ACIDS; Ferocenophane; SIMPLE ALKALOIDS; DERIVATIVES
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202000414

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 π 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 π system on the iron atom is reflected by results of cyclovoltammetric measurements. New conjugates of quinazoline alkaloids with ferrocene are reported. The compounds form highly extended conjugated π systems. The structures indicate an almost coplanar conformation of the substituents and the cyclopentadienyl ligands.