English   español  
Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/152530
Título

Synthesis, regioselectivity, and DFT analysis of new antioxidant pyrazolo[4,3-c]quinoline-3,4-diones

AutorTomassoli, I.; Herlem, G.; Picaud, F.; Benchekroun, M.; Bautista-Aguilera, Óscar M.; Luzet, V.; Jimeno, M. Luisa; Gharbi, T.; Refouvelet, B.; Ismaili, L.
Palabras claveAntioxidants
Density functional theory
Pyrazoloquinolines
Kinetic control
Isomers
Fecha de publicación2016
EditorSpringer
CitaciónMonatshefte für Chemie 147: 1069-1079 (2016)
ResumenThe condensation of hydrazine, N-methylhydrazine, and N-phenylhydrazine with ethyl 4-chloro-2-oxo- 1,2-dihydroquinoline-3-carboxylate derivatives has been investigated. As a result, 12 new antioxidant pyrazolo[4,3- c]quinolin-3,4-diones were obtained with good to high yields. When two cross-products could be possible, only one isomer bearing the methyl or the phenyl group at the N1 position is isolated and unequivocally characterized using 1D and 2D NMR techniques, FT-IR, and combustion analyses. DFT analysis of the reaction mechanism was carried out in the Pearson’s hard soft acid base framework, confirming the assigned structure to the observed pyrazolo[4,3-c]quinolin-3,4-diones. These calculations indicate a favored kinetic control for the synthesized pyrazolo[4,3- c]quinolin-3,4-diones compared to its possible regioisomer.
Versión del editorhttp://dx.doi.org/10.1007/s00706-016-1660-7
URIhttp://hdl.handle.net/10261/152530
DOI10.1007/s00706-016-1660-7
Identificadoresdoi: 10.1007/s00706-016-1660-7
issn: 0026-9247
e-issn: 1434-4475
Aparece en las colecciones: (CENQUIOR) Artículos
Ficheros en este ítem:
Fichero Descripción Tamaño Formato  
accesoRestringido.pdf15,38 kBAdobe PDFVista previa
Visualizar/Abrir
Mostrar el registro completo
 

Artículos relacionados:


NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.