Efficient one-pot synthesis of 3,7-disubstituted 1,6-naphthyridin-2(1H)-ones through regioselective palladium-catalyzed cross-coupling and SNAr reactions

Abstract

An efficient synthesis of original 3,7-disubstituted 1,6-naphthyridones via one-pot palladium-catalyzed cross-coupling and SNAr 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 SNAr reactions were employed to functionalize the position 7. This one-pot approach afforded highly functionalized 1,6-naphthyridin-2(1H)-ones in good yields.