Efficient one-pot synthesis of 3, 7-disubstituted 1, 6-naphthyridin-2(1H)-ones through regioselective palladium-catalyzed cross-coupling and SNAr reactions. Issue 21 (27th May 2015)

• Record Type: Journal Article
• Authors: Montoir, David; Tonnerre, Alain; Duflos, Muriel; Bazin, Marc-Antoine
• Is Part Of: Tetrahedron. Volume 71:Issue 21(2015)
• Page Start: 3303
• Page End: 3313
• Publication Date: 2015-05-27
• Subjects: Nitrogen-containing heterocycles -- C–N bond formation -- Buchwald–Hartwig coupling -- Suzuki–Miyaura cross-coupling -- Nucleophilic aromatic substitution; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.03.110
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An efficient synthesis of original 3, 7-disubstituted 1, 6-naphthyridones via one-pot palladium-catalyzed cross-coupling and SN Ar reactions is reported. Buchwald–Hartwig amination was investigated to introduce a large variety of nitrogen-containing nucleophiles at position 3 of 1, 6-naphthyridones. Then, palladium-catalyzed C - and N -arylation or SN Ar reactions were employed to functionalize the position 7. This one-pot approach afforded highly functionalized 1, 6-naphthyridin-2(1 H )-ones in good yields. Graphical abstract: