TY - JOUR

T1 - Novel π-Extended Quinazoline-Ferrocene Conjugates

T2 - Synthesis, Structure, and Redox Behavior

AU - Elmuradov, Burkhon

AU - Dräger, Gerald

AU - Butenschön, Holger

N1 - Funding information: We gratefully acknowledge a Georg Forster Research Fellowship for Experienced Researchers of the Alexander von Humboldt Foundation (AvH) for B. E. (UZB 1186936 GF-E). We are indebted to Innospec Deutschland GmbH for a donation of ferrocene. We gratefully acknowledge a Georg Forster Research Fellowship for Experienced Researchers of the Alexander von Humboldt Foundation (AvH) for B. E. (UZB 1186936 GF?E). We are indebted to Innospec Deutschland GmbH for a donation of ferrocene.

PY - 2020/6/17

Y1 - 2020/6/17

N2 - 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.

AB - 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.

KW - Alkaloids

KW - Extended π systems

KW - Ferocenophane

KW - Ferrocene

KW - Sandwich complexes

UR - http://www.scopus.com/inward/record.url?scp=85085108117&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202000414

DO - 10.1002/ejoc.202000414

M3 - Article

AN - SCOPUS:85085108117

VL - 2020

SP - 3430

EP - 3440

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 23

ER -