Details
| Original language | English |
|---|---|
| Pages (from-to) | 3430-3440 |
| Number of pages | 11 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2020 |
| Issue number | 23 |
| Early online date | 7 Apr 2020 |
| Publication status | Published - 17 Jun 2020 |
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 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.
Keywords
- Alkaloids, Extended π systems, Ferocenophane, Ferrocene, Sandwich complexes
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, Vol. 2020, No. 23, 17.06.2020, p. 3430-3440.
Research output: Contribution to journal › Article › Research › peer review
}
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 -