Convenient synthesis and characterization of molecules containing multiple β-keto ester units

Julio Belmar, Leandro Ortiz, Denis Ramírez, Fabiola Fuentes, María Parra, Verónica A. Jiménez, Claudio A. Jiménez

Resultado de la investigación: Article

2 Citas (Scopus)

Resumen

Three compounds containing two β-keto ester units and one containing three were obtained in good yields from sebacyl, terepthaloyl, isophthaloyl, and trimesoyl chlorides. In this one pot procedure the acid chlorides were first treated with ethyl acetoacetate and barium oxide and then with ethyl alcohol. The aliphatic ester exists mainly as keto ester with a very small amount of the enol tautomer. In the case of aromatic esters, all possible tautomers were found in considerable concentrations in deuterochloroform solution. Theoretical chemical shifts were estimated from GIAO/WP04/aug - cc-pVDZ/SCRF calculations, for a probable signal assignation for the corresponding tautomeric species. Our theoretical results are in agreement with experimental findings and account for negligible stability differences between the tautomers of each aromatic compound.

Idioma originalEnglish
Páginas (desde-hasta)4984-4988
Número de páginas5
PublicaciónTetrahedron Letters
Volumen53
N.º37
DOI
EstadoPublished - 12 sep 2012

Huella dactilar

Esters
Molecules
Chlorides
Aromatic compounds
Chemical shift
Ethanol
Acids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Citar esto

Belmar, Julio ; Ortiz, Leandro ; Ramírez, Denis ; Fuentes, Fabiola ; Parra, María ; Jiménez, Verónica A. ; Jiménez, Claudio A. / Convenient synthesis and characterization of molecules containing multiple β-keto ester units. En: Tetrahedron Letters. 2012 ; Vol. 53, N.º 37. pp. 4984-4988.
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abstract = "Three compounds containing two β-keto ester units and one containing three were obtained in good yields from sebacyl, terepthaloyl, isophthaloyl, and trimesoyl chlorides. In this one pot procedure the acid chlorides were first treated with ethyl acetoacetate and barium oxide and then with ethyl alcohol. The aliphatic ester exists mainly as keto ester with a very small amount of the enol tautomer. In the case of aromatic esters, all possible tautomers were found in considerable concentrations in deuterochloroform solution. Theoretical chemical shifts were estimated from GIAO/WP04/aug - cc-pVDZ/SCRF calculations, for a probable signal assignation for the corresponding tautomeric species. Our theoretical results are in agreement with experimental findings and account for negligible stability differences between the tautomers of each aromatic compound.",
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Belmar, J, Ortiz, L, Ramírez, D, Fuentes, F, Parra, M, Jiménez, VA & Jiménez, CA 2012, 'Convenient synthesis and characterization of molecules containing multiple β-keto ester units', Tetrahedron Letters, vol. 53, n.º 37, pp. 4984-4988. https://doi.org/10.1016/j.tetlet.2012.07.025

Convenient synthesis and characterization of molecules containing multiple β-keto ester units. / Belmar, Julio; Ortiz, Leandro; Ramírez, Denis; Fuentes, Fabiola; Parra, María; Jiménez, Verónica A.; Jiménez, Claudio A.

En: Tetrahedron Letters, Vol. 53, N.º 37, 12.09.2012, p. 4984-4988.

Resultado de la investigación: Article

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T1 - Convenient synthesis and characterization of molecules containing multiple β-keto ester units

AU - Belmar, Julio

AU - Ortiz, Leandro

AU - Ramírez, Denis

AU - Fuentes, Fabiola

AU - Parra, María

AU - Jiménez, Verónica A.

AU - Jiménez, Claudio A.

PY - 2012/9/12

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AB - Three compounds containing two β-keto ester units and one containing three were obtained in good yields from sebacyl, terepthaloyl, isophthaloyl, and trimesoyl chlorides. In this one pot procedure the acid chlorides were first treated with ethyl acetoacetate and barium oxide and then with ethyl alcohol. The aliphatic ester exists mainly as keto ester with a very small amount of the enol tautomer. In the case of aromatic esters, all possible tautomers were found in considerable concentrations in deuterochloroform solution. Theoretical chemical shifts were estimated from GIAO/WP04/aug - cc-pVDZ/SCRF calculations, for a probable signal assignation for the corresponding tautomeric species. Our theoretical results are in agreement with experimental findings and account for negligible stability differences between the tautomers of each aromatic compound.

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KW - β-Triketotriester

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