Substituted 4‐Oxo‐1,2,3,4‐tetrahydroquinoline‐3‐carboxylic Esters by a Tandem Imine Addition‐S_NAr Reaction

Recent Syntheses of 1,2,3,4-Tetrahydroquinolines, 2,3-Dihydro-4(1H)-quinolinones and 4(1H)-Quinolinones using Domino Reactions

“…Bunce and Schammerhorn have described a new domino strategy for the synthesis of highly substituted 2,3-dihydro-4( 1H )-quinolinones using an imine addition-S N Ar approach [89]. Reaction of tert -butyl 2-fluoro-5-nitrobenzoylacetate ( 82 ) with pre-formed imines 83 at room temperature furnished the target compounds 84 in a single operation.…”

Domino Aldol-SNAr-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1H)-ones and 1,8-Naphthyridin-2(1H)-ones

“…More recent projects have broadened the scope of these processes. One study described an imine addition-S N Ar reaction to tert-butyl (2-fluoro-5-nitrobenzoyl)acetate to give 4-oxo-1,2,3,4-tetrahydroquinoline-3carboxylic esters [2]. Further use of domino procedures on Morita-Baylis-Hillman acetates afforded efficient access to naphthalenes and quinolines [3] as well as dihydroquinolines, dihydronaphthyridines and quinolin-4(1H)-ones [4].…”

“…(1) (2) Four additional papers explored additions of nitrogen heterocycles to allylic esters. Tong and co-workers reported access to thiopyrano [2,3-b]indoles by addition of indoline-2-thiones to β-acetoxy allenoates (Reaction (3)) [9].…”

Synthesis and Photophysical Characterization of 2,3‐Dihydroquinolin‐4‐imines: New Fluorophores with Color‐Tailored Emission

“…Lu and co‐workers have reported the asymmetric synthesis of 2‐aryl‐2,3‐dihydro‐4(1 H )‐quinolinones using a chiral tertiary amine tethered to a bifunctional thiourea derivative (Scheme c) . Bunce and co‐workers have reported a strategy for the synthesis of substituted 2,3‐dihydro‐4(1 H )‐quinolinones by the addition of an imine by an S N Ar approach (Scheme d) . As shown in Scheme , all the above‐mentioned methods have utilized suitable ortho ‐substituents of anilines or fluorobenzene for participating in cyclization.…”

“…[8] Bunce and co-workers have reported as trategy for the synthesis of substituted2 ,3-dihydro-4(1H)-quinolinones by the addition of an imine by an S N Ar approach( Scheme1d). [9] As shown in Scheme 1, all the above-mentionedm ethods have utilized suitable ortho-substituents of anilineso rf luorobenzenef or participating in cyclization. The preparation of the startingd isubstitutedb enzenes is tedious and time-consuming.…”