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1‐Alkyl‐2,3‐dihydro‐4(1 H )‐quinolinones by a tandem Michael‐S N Ar annulation reaction
Author(s) -
Bunce Richard A.,
Nago Takahiro
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.70
Subject(s) - chemistry , annulation , tandem , ring (chemistry) , alkyl , michael reaction , dimethylformamide , medicinal chemistry , stereochemistry , cascade reaction , organic chemistry , catalysis , materials science , solvent , composite material
A tandem Michael‐S N Ar annulation reaction has been developed for the synthesis of 1‐alkyl‐2,3‐dihydro‐4(1 H )‐quinolinones. Success in the reaction followed expected electronic effects for the final S N Ar 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(1 H )‐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).