Facile synthesis of 3-substituted isoindolinones

Quaternary Ammonium Salt‐Promoted Multi‐Component Reaction in Water: Access to 3‐Alkyl‐2, 3‐Dihydro‐1H‐Isoindolin‐1‐One Derivatives

“…3‐(2‐oxo‐2‐phenylethyl)‐2‐(p–tolyl)isoindolin‐1‐one (5 p) . White solid, 81% yield, m.p.=179–180 °C.…”

Expedient and Diastereoselective Synthesis of Substituted 6,6a-Dihydroisoindolo[2,1-a]quinolin-11(5H)-ones

“…18 In continuation of our previous studies on the development of various synthetic methodologies, [18][19][20][21][22][23][24] we have recently reported the synthesis of 3-substituted 2-arylisoindolin-1-ones in 56-96% yields from N-aryl-3-hydroxyisoindolinones and diverse alkyl aryl ketones such as acetophenones, 1-indanones, and α-tetralones in one step (C-C bond formation) under Lewis acid catalyzed microwave heating conditions (Scheme 1). 25 These reactions apparently involve the formation of N-acyliminium ion intermediate. This approach provided a new strategy for the synthesis of 3-(2-oxo-2-arylethyl)-substituted 2-arylisoindolin-1-ones 1a-p from inexpensive starting materials.…”

“…The proposed strategy provides an alternate approach for the synthesis of 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones. Although such compounds have been synthesized in one step by the Aza-Diels-Alder reactions of 3-hydroxy-2-arylisoindol-1-ones with olefins, 11 the proposed two-step reaction sequence offers several advantages: i) it constitutes a new and versatile synthetic procedure, ii) new intermediates are produced en route that may have potential applications, 25 and iii) higher commercial availability of diverse alkyl aryl ketones compared to styrene-type starting materials for the one-step Aza-Diels-Alder reactions. 11 The syntheses of starting materials, substituted isoindolinones 1a-p, were recently reported by us.…”

“…11 The syntheses of starting materials, substituted isoindolinones 1a-p, were recently reported by us. 25 This study presents their further synthetic transformations. First, the reduction of the keto group of 3-(2-oxo-2-phenylethyl)-2phenylisoindolin-1-one (1a) with NaBH 4 afforded the corresponding alcohol, 3-(2-hydroxy-2-phenylethyl)-2phenylisoindolin-1-one (2a) in 85% yield (Table 1, entry 1, compound 2a).…”

“…Starting materials were purchased from commercial sources and used as received without further purification; 3-substituted N-arylisoindolinones 1a-p were prepared and characterized following the previous report from our group. 25 Toluene was refluxed using a Dean-Stark apparatus to remove H 2 O. Precoated silica gel 60 F-254 TLC plates (0.25 mm) was used to monitor the progress of the reactions and visualized using UV irradiation. Silica gel of particle size 230-400 mesh was used for column chromatography.…”