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Title

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

AuthorsTomassoli, I.; Herlem, G.; Picaud, F.; Benchekroun, M.; Bautista-Aguilera, Óscar M.; Luzet, V.; Jimeno, M. Luisa; Gharbi, T.; Refouvelet, B.; Ismaili, L.
KeywordsAntioxidants
Density functional theory
Pyrazoloquinolines
Kinetic control
Isomers
Issue Date2016
PublisherSpringer
CitationMonatshefte für Chemie 147: 1069-1079 (2016)
AbstractThe 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.
Publisher version (URL)http://dx.doi.org/10.1007/s00706-016-1660-7
URIhttp://hdl.handle.net/10261/152530
DOI10.1007/s00706-016-1660-7
Identifiersdoi: 10.1007/s00706-016-1660-7
issn: 0026-9247
e-issn: 1434-4475
Appears in Collections:(CENQUIOR) Artículos

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