4-[(Dimethylamino)methylene]-2-ferrocenyl-5-oxo-4,5-dihydrofuran-3- carboxaldehyde: Synthesis, spectral characterization and single crystal X-ray analysis

Zoran Ratković, Jovana Muškinja, Sladjana B. Novaković, Goran A. Bogdanović, K. Micskei, Rastko D. Vukićević

Research output: Contribution to journalArticle

Abstract

The title compound 4-[(dimethylamino)methylene]-2-ferrocenyl-5-oxo-4,5- dihydrofuran-3-carboxaldehyde was synthesized by reacting 3-ferrocenoylpropionic acid with Vilsmeier reagent. This result is rather unexpected, since 3-aroylpropanoic acids under these conditions usually give the corresponding 2-aryl-4-chloro-3-formylfurans. 3-Ferrocenoylpropanoic acid is not the only 3-aroylpropanoic acid that exhibit an unusual behavior under the same conditions: 3-thenoylpropanoic acid gave 4-[(dimethylamino)-methylene]-2-(2- thienyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 4-[(dimethylamino) methylene]-2-(2-thienyl-5-formyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde, whereas 3-(4-methoxybenzoyl)propanoic acid yielded 4-[(dimethylamino)methylene]- 2-(4-methoxyphenyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 2-(4-methoxyphenyl)-5-chloro-furan-3,4-dicarboxaldehyde. Single crystal X-ray analysis was successfully performed for 4-[(dimethylamino)methylene]-2- ferrocenyl-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 4-[(dimethylamino) methylene]-2-(2-thienyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and their structures were compared.

Original languageEnglish
Pages (from-to)193-197
Number of pages5
JournalPolyhedron
Volume80
DOIs
Publication statusPublished - Sep 25 2014

Fingerprint

X ray analysis
methylene
Single crystals
acids
Acids
single crystals
synthesis
crystals
x rays
furans
reagents

Keywords

  • 3-Aroylpropanoic acids
  • 3-Ferocenoylpropanoic acid
  • Crystal structure
  • Furan derivatives
  • Vilsmeier reagent

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Materials Chemistry
  • Physical and Theoretical Chemistry

Cite this

4-[(Dimethylamino)methylene]-2-ferrocenyl-5-oxo-4,5-dihydrofuran-3- carboxaldehyde : Synthesis, spectral characterization and single crystal X-ray analysis. / Ratković, Zoran; Muškinja, Jovana; Novaković, Sladjana B.; Bogdanović, Goran A.; Micskei, K.; Vukićević, Rastko D.

In: Polyhedron, Vol. 80, 25.09.2014, p. 193-197.

Research output: Contribution to journalArticle

Ratković, Zoran ; Muškinja, Jovana ; Novaković, Sladjana B. ; Bogdanović, Goran A. ; Micskei, K. ; Vukićević, Rastko D. / 4-[(Dimethylamino)methylene]-2-ferrocenyl-5-oxo-4,5-dihydrofuran-3- carboxaldehyde : Synthesis, spectral characterization and single crystal X-ray analysis. In: Polyhedron. 2014 ; Vol. 80. pp. 193-197.
@article{f80cbac120b241a6968f516f604470a5,
title = "4-[(Dimethylamino)methylene]-2-ferrocenyl-5-oxo-4,5-dihydrofuran-3- carboxaldehyde: Synthesis, spectral characterization and single crystal X-ray analysis",
abstract = "The title compound 4-[(dimethylamino)methylene]-2-ferrocenyl-5-oxo-4,5- dihydrofuran-3-carboxaldehyde was synthesized by reacting 3-ferrocenoylpropionic acid with Vilsmeier reagent. This result is rather unexpected, since 3-aroylpropanoic acids under these conditions usually give the corresponding 2-aryl-4-chloro-3-formylfurans. 3-Ferrocenoylpropanoic acid is not the only 3-aroylpropanoic acid that exhibit an unusual behavior under the same conditions: 3-thenoylpropanoic acid gave 4-[(dimethylamino)-methylene]-2-(2- thienyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 4-[(dimethylamino) methylene]-2-(2-thienyl-5-formyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde, whereas 3-(4-methoxybenzoyl)propanoic acid yielded 4-[(dimethylamino)methylene]- 2-(4-methoxyphenyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 2-(4-methoxyphenyl)-5-chloro-furan-3,4-dicarboxaldehyde. Single crystal X-ray analysis was successfully performed for 4-[(dimethylamino)methylene]-2- ferrocenyl-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 4-[(dimethylamino) methylene]-2-(2-thienyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and their structures were compared.",
keywords = "3-Aroylpropanoic acids, 3-Ferocenoylpropanoic acid, Crystal structure, Furan derivatives, Vilsmeier reagent",
author = "Zoran Ratković and Jovana Muškinja and Novaković, {Sladjana B.} and Bogdanović, {Goran A.} and K. Micskei and Vukićević, {Rastko D.}",
year = "2014",
month = "9",
day = "25",
doi = "10.1016/j.poly.2014.03.038",
language = "English",
volume = "80",
pages = "193--197",
journal = "Polyhedron",
issn = "0277-5387",
publisher = "Elsevier Limited",

}

TY - JOUR

T1 - 4-[(Dimethylamino)methylene]-2-ferrocenyl-5-oxo-4,5-dihydrofuran-3- carboxaldehyde

T2 - Synthesis, spectral characterization and single crystal X-ray analysis

AU - Ratković, Zoran

AU - Muškinja, Jovana

AU - Novaković, Sladjana B.

AU - Bogdanović, Goran A.

AU - Micskei, K.

AU - Vukićević, Rastko D.

PY - 2014/9/25

Y1 - 2014/9/25

N2 - The title compound 4-[(dimethylamino)methylene]-2-ferrocenyl-5-oxo-4,5- dihydrofuran-3-carboxaldehyde was synthesized by reacting 3-ferrocenoylpropionic acid with Vilsmeier reagent. This result is rather unexpected, since 3-aroylpropanoic acids under these conditions usually give the corresponding 2-aryl-4-chloro-3-formylfurans. 3-Ferrocenoylpropanoic acid is not the only 3-aroylpropanoic acid that exhibit an unusual behavior under the same conditions: 3-thenoylpropanoic acid gave 4-[(dimethylamino)-methylene]-2-(2- thienyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 4-[(dimethylamino) methylene]-2-(2-thienyl-5-formyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde, whereas 3-(4-methoxybenzoyl)propanoic acid yielded 4-[(dimethylamino)methylene]- 2-(4-methoxyphenyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 2-(4-methoxyphenyl)-5-chloro-furan-3,4-dicarboxaldehyde. Single crystal X-ray analysis was successfully performed for 4-[(dimethylamino)methylene]-2- ferrocenyl-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 4-[(dimethylamino) methylene]-2-(2-thienyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and their structures were compared.

AB - The title compound 4-[(dimethylamino)methylene]-2-ferrocenyl-5-oxo-4,5- dihydrofuran-3-carboxaldehyde was synthesized by reacting 3-ferrocenoylpropionic acid with Vilsmeier reagent. This result is rather unexpected, since 3-aroylpropanoic acids under these conditions usually give the corresponding 2-aryl-4-chloro-3-formylfurans. 3-Ferrocenoylpropanoic acid is not the only 3-aroylpropanoic acid that exhibit an unusual behavior under the same conditions: 3-thenoylpropanoic acid gave 4-[(dimethylamino)-methylene]-2-(2- thienyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 4-[(dimethylamino) methylene]-2-(2-thienyl-5-formyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde, whereas 3-(4-methoxybenzoyl)propanoic acid yielded 4-[(dimethylamino)methylene]- 2-(4-methoxyphenyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 2-(4-methoxyphenyl)-5-chloro-furan-3,4-dicarboxaldehyde. Single crystal X-ray analysis was successfully performed for 4-[(dimethylamino)methylene]-2- ferrocenyl-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and 4-[(dimethylamino) methylene]-2-(2-thienyl)-5-oxo-4,5-dihydrofuran-3-carboxaldehyde and their structures were compared.

KW - 3-Aroylpropanoic acids

KW - 3-Ferocenoylpropanoic acid

KW - Crystal structure

KW - Furan derivatives

KW - Vilsmeier reagent

UR - http://www.scopus.com/inward/record.url?scp=84905442719&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84905442719&partnerID=8YFLogxK

U2 - 10.1016/j.poly.2014.03.038

DO - 10.1016/j.poly.2014.03.038

M3 - Article

AN - SCOPUS:84905442719

VL - 80

SP - 193

EP - 197

JO - Polyhedron

JF - Polyhedron

SN - 0277-5387

ER -