Novel approach towards 3,7-disubstituted 1,6-naphthyridin-4(1H)-ones exploiting cross-coupling and SNAr reactions of a dihalogenated compound

[Display omitted] •A new access to 3,7-disubstituted 1,6-naphthyridin-4(1H)-ones.•Differential functionalization of 1,6-naphthyridin-4(1H)-ones.•Palladium-catalyzed cross-coupling reactions and SNAr reactions. A new route towards the synthesis of a series of 3,7-disubstituted 1,6-naphthyridin-4(1H)-...

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Bibliographic Details
Published in:Tetrahedron letters 2018-09, Vol.59 (39), p.3519-3523
Main Authors: Dembélé, Ousmane, Montoir, David, Yvorra, Thomas, Sérillon, Dylan, Tonnerre, Alain, Duflos, Muriel, Robert, Jean-Michel, Bazin, Marc-Antoine
Format: Article
Language:English
Subjects:
1,6-Naphthyridin-4(1H)-ones
Buchwald-Hartwig amination
Halodecarboxylation
Nucleophilic aromatic substitution
Suzuki-Miyaura reaction
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Summary:[Display omitted] •A new access to 3,7-disubstituted 1,6-naphthyridin-4(1H)-ones.•Differential functionalization of 1,6-naphthyridin-4(1H)-ones.•Palladium-catalyzed cross-coupling reactions and SNAr reactions. A new route towards the synthesis of a series of 3,7-disubstituted 1,6-naphthyridin-4(1H)-ones in moderate to good yields is reported. The strategy involves the preparation of a 3,7-dihalogenated compound that undergoes differential functionalization using palladium-catalyzed cross-coupling and SNAr reactions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.08.013