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Inicio » Actividades I+D > Publicaciones 2017 > Alkylation of 2- and 3-alkoxycarbonyl-4-...
artículo con referato
"Alkylation of 2- and 3-alkoxycarbonyl-4-quinolinones. DFT study on the regioselectivity"
María S. Shmidt, Pau Arroyo Mañez, Carlos A. Stortz, Isabel A. Perillo, Daniel Vega and María M. Blanco
J. Mol. Struct. 1128 (2017) 142-150
The reaction of 2-alkoxycarbonyl-4-quinolinones (1) with a variety of alkylating reagents under different conditions, lead to the corresponding O-alkylated products. The behavior in basic medium of compounds 1 differs from the 3-alkoxycarbonyl-4-quinolinones (4) isomers suggesting that the position of the carboxylate group determines the regioselectivity of the reaction. DFT calculations allow us to conclude that for 3-alkoxycarbonyl-4-quinolinones, the N-alkylation would be thermodynamically and kinetically favored. But for 2-alkoxycarbonyl-4-quinolinones the side chain in the 2-position of the ring prevents the planar approximation to the contiguous heteroatom leading to a more favorable O-alkylation transition state. Crystal structure of an O-alkylated product is determined by single crystal X-ray diffractometry.
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