Abstract
Abstract magnified imageA tandem Michael‐SNAr annulation reaction has been developed for the synthesis of 1‐alkyl‐2,3‐dihydro‐4(1H)‐quinolinones. Success in the reaction followed expected electronic effects for the final SNAr ring closure. Treatment of doubly activated 1‐(2‐fluoro‐5‐nitrophenyl)‐2‐propen‐1‐one with primary amines in N,N‐dimethylformamide at 50°C for 24 h provided 2,3‐dihydro‐4(1H)‐quinolinones in 67–78% yields. Singly activated 1‐(2‐fluorophenyl)‐2‐propen‐1‐one reacted similarly, but failed to undergo the final ring closure with hindered or aromatic amines. Finally, 1‐(2‐fluoro‐5‐methoxyphenyl)‐2‐propen‐1‐one, with one activating and one deactivating group on the ring, gave only simple 1,4‐addition products. J. Heterocyclic Chem., (2009).
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