Alkylation of 2- and 3-alkoxycarbonyl-4-quinolinones. DFT study on the regioselectivity
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...
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| Autores principales: | , |
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2017
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v1128_n_p142_Shmidt http://hdl.handle.net/20.500.12110/paper_00222860_v1128_n_p142_Shmidt |
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| Sumario: | 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. © 2016 Elsevier B.V. |
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