4-[(Dimethylamino)methylene]-2-ferrocenyl-5-oxo-4, 5-dihydrofuran-3-carboxaldehyde: Synthesis, spectral characterization and single crystal X-ray analysis
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Ratković, Zoran R.Muškinja, Jovana
Novaković, Slađana B.
Bogdanović, Goran A.
Micskei, Karoly
Vukićević, Rastko D.
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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-carb...oxaldehyde and 4-[(dimethylamino)methylene]-2-(2-thienyl)-5-oxo-4, 5-dihydrofuran-3-carboxaldehyde and their structures were compared. (C) 2014 Elsevier Ltd. All rights reserved.
Keywords:
3-Aroylpropanoic acids / 3-Ferocenoylpropanoic acid / Vilsmeier reagent / Furan derivatives / Crystal structureSource:
Polyhedron, 2014, 80, SI, 193-197Funding / projects:
- Novel Electrochemical and Chemical Methods in Synthesis of Organic Compounds of Interest for Medicine and Material Chemistry (RS-MESTD-Basic Research (BR or ON)-172034)
- Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds (RS-MESTD-Basic Research (BR or ON)-172014)
DOI: 10.1016/j.poly.2014.03.038
ISSN: 0277-5387
WoS: 000341348300025
Scopus: 2-s2.0-84905442719
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VinčaTY - JOUR AU - Ratković, Zoran R. AU - Muškinja, Jovana AU - Novaković, Slađana B. AU - Bogdanović, Goran A. AU - Micskei, Karoly AU - Vukićević, Rastko D. PY - 2014 UR - https://vinar.vin.bg.ac.rs/handle/123456789/101 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. (C) 2014 Elsevier Ltd. All rights reserved. T2 - Polyhedron T1 - 4-[(Dimethylamino)methylene]-2-ferrocenyl-5-oxo-4, 5-dihydrofuran-3-carboxaldehyde: Synthesis, spectral characterization and single crystal X-ray analysis VL - 80 IS - SI SP - 193 EP - 197 DO - 10.1016/j.poly.2014.03.038 ER -
@article{ author = "Ratković, Zoran R. and Muškinja, Jovana and Novaković, Slađana B. and Bogdanović, Goran A. and Micskei, Karoly and Vukićević, Rastko D.", year = "2014", 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. (C) 2014 Elsevier Ltd. All rights reserved.", journal = "Polyhedron", title = "4-[(Dimethylamino)methylene]-2-ferrocenyl-5-oxo-4, 5-dihydrofuran-3-carboxaldehyde: Synthesis, spectral characterization and single crystal X-ray analysis", volume = "80", number = "SI", pages = "193-197", doi = "10.1016/j.poly.2014.03.038" }
Ratković, Z. R., Muškinja, J., Novaković, S. B., Bogdanović, G. A., Micskei, K.,& Vukićević, R. D.. (2014). 4-[(Dimethylamino)methylene]-2-ferrocenyl-5-oxo-4, 5-dihydrofuran-3-carboxaldehyde: Synthesis, spectral characterization and single crystal X-ray analysis. in Polyhedron, 80(SI), 193-197. https://doi.org/10.1016/j.poly.2014.03.038
Ratković ZR, Muškinja J, Novaković SB, Bogdanović GA, Micskei K, Vukićević RD. 4-[(Dimethylamino)methylene]-2-ferrocenyl-5-oxo-4, 5-dihydrofuran-3-carboxaldehyde: Synthesis, spectral characterization and single crystal X-ray analysis. in Polyhedron. 2014;80(SI):193-197. doi:10.1016/j.poly.2014.03.038 .
Ratković, Zoran R., Muškinja, Jovana, Novaković, Slađana B., Bogdanović, Goran A., Micskei, Karoly, 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, 80, no. SI (2014):193-197, https://doi.org/10.1016/j.poly.2014.03.038 . .