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: Contribución a una revistaArtículo

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

Áreas temáticas de ASJC Scopus

  • Bioquímica
  • Descubrimiento de medicamentos
  • Química orgánica

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