Details
| Original language | English |
|---|---|
| Pages (from-to) | 483-492 |
| Number of pages | 10 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2016 |
| Issue number | 3 |
| Publication status | Published - 9 Dec 2015 |
Abstract
The first organometallic derivatives of tricyclic quinazoline derivatives are prepared by condensation of the active C-3 methylene group of 7H-deoxyvasicinones with ferrocenecarbaldehyde. By following this route the conjugated parent alkaloid and derivatives with nitro, amino, as well as some alkanoylamino groups at C-7 were attached at the ferrocene moiety, thereby significantly extending the π system. In addition, the parent compound was subjected to the reaction by treatment with ferrocene-1,1′-dicarbaldehyde, giving rise to the double condensation product, which is only the second case of a 1,1′-disubstituted ferrocene derivative with two alkaloid substituents. A number of the compounds obtained were subjected to X-ray crystallographic analyses. In all cases, the substituents adopt a coplanar conformation with the ferrocene cyclopentadienyl ligands. The influence of the substituents at C-7 through the extended conjugated π system on the iron atom is reflected by results of cyclic voltammetric measurements as well as by DFT calculations. 7H-Deoxyvasicinones are condensed with ferrocenecarbaldehyde and with ferrocene-1,1′-dicarbaldehyde to generate extended π systems with coplanar conformations of the two moieties. The products are investigated by crystal structure analyses, cyclic voltammetry, and DFT calculations.
Keywords
- Alkaloids, Cyclic voltammetry, Metallocenes, Pi interactions, Redox chemistry, 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. 2016, No. 3, 09.12.2015, p. 483-492.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Tricyclic quinazoline alkaloids conjugated to ferrocene
T2 - Synthesis, structure, and redox behavior of ferrocenylmethylene-substituted 7H-deoxyvasicinones
AU - Elmuradov, Burkhon
AU - Shakhidoyatov, Khusnutdin
AU - Dräger, Gerald
AU - Butenschön, Holger
PY - 2015/12/9
Y1 - 2015/12/9
N2 - The first organometallic derivatives of tricyclic quinazoline derivatives are prepared by condensation of the active C-3 methylene group of 7H-deoxyvasicinones with ferrocenecarbaldehyde. By following this route the conjugated parent alkaloid and derivatives with nitro, amino, as well as some alkanoylamino groups at C-7 were attached at the ferrocene moiety, thereby significantly extending the π system. In addition, the parent compound was subjected to the reaction by treatment with ferrocene-1,1′-dicarbaldehyde, giving rise to the double condensation product, which is only the second case of a 1,1′-disubstituted ferrocene derivative with two alkaloid substituents. A number of the compounds obtained were subjected to X-ray crystallographic analyses. In all cases, the substituents adopt a coplanar conformation with the ferrocene cyclopentadienyl ligands. The influence of the substituents at C-7 through the extended conjugated π system on the iron atom is reflected by results of cyclic voltammetric measurements as well as by DFT calculations. 7H-Deoxyvasicinones are condensed with ferrocenecarbaldehyde and with ferrocene-1,1′-dicarbaldehyde to generate extended π systems with coplanar conformations of the two moieties. The products are investigated by crystal structure analyses, cyclic voltammetry, and DFT calculations.
AB - The first organometallic derivatives of tricyclic quinazoline derivatives are prepared by condensation of the active C-3 methylene group of 7H-deoxyvasicinones with ferrocenecarbaldehyde. By following this route the conjugated parent alkaloid and derivatives with nitro, amino, as well as some alkanoylamino groups at C-7 were attached at the ferrocene moiety, thereby significantly extending the π system. In addition, the parent compound was subjected to the reaction by treatment with ferrocene-1,1′-dicarbaldehyde, giving rise to the double condensation product, which is only the second case of a 1,1′-disubstituted ferrocene derivative with two alkaloid substituents. A number of the compounds obtained were subjected to X-ray crystallographic analyses. In all cases, the substituents adopt a coplanar conformation with the ferrocene cyclopentadienyl ligands. The influence of the substituents at C-7 through the extended conjugated π system on the iron atom is reflected by results of cyclic voltammetric measurements as well as by DFT calculations. 7H-Deoxyvasicinones are condensed with ferrocenecarbaldehyde and with ferrocene-1,1′-dicarbaldehyde to generate extended π systems with coplanar conformations of the two moieties. The products are investigated by crystal structure analyses, cyclic voltammetry, and DFT calculations.
KW - Alkaloids
KW - Cyclic voltammetry
KW - Metallocenes
KW - Pi interactions
KW - Redox chemistry
KW - Sandwich complexes
UR - http://www.scopus.com/inward/record.url?scp=84957849892&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201501307
DO - 10.1002/ejoc.201501307
M3 - Article
AN - SCOPUS:84957849892
VL - 2016
SP - 483
EP - 492
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 3
ER -