Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones from 2-formylbenzoic acid

A one-pot, three-component and solvent-free synthesis of 2,3-disubstituted isoindolin-1-ones

“…18,19 However, few syntheses of these heterocycles using 2-formylbenzoic acid can be found in the literature. [20][21][22][23][24] In accordance with the increasing need to develop new and simple methods to prepare these biologically active heterocyclic compounds, and in a continuation of our previous studies on the development of efficient methods for the synthesis of biologically active heterocyclic compounds, 25 we herein report a novel synthesis of 2,3-disubstituted isoindolin-1-ones via a one-pot, three-component reaction between 2-formylbenzoic acid, a CH-acid, and a benzylamine.The reaction of 2-formylbenzoic acid 1, dimedone 2a, and benzylamine 3a was selected as a model reaction (Scheme 1), for which the reaction conditions would be optimized. We investigated the effect of solvent, various temperatures and reaction time on the yield of isoindolin-1-one 4a.…”

Alkali‐Metal Promoted Chemo‐ and Regioselective Cycloisomerization Reactions to (Z)‐3‐Alkylideneisoindolin‐1‐ones: Unusual Positive Role of H2O

“…Wang et al described an improved synthesis of 3‐alkylisoindolin‐1‐ones from phthalimide and organometallic reagents, through alkylation, dehydration, and with concomitant reduction by sodium cyanoborohydrate in an acidic medium . In addition, a Horner reaction between phosphorylated isoindolinones and aryl aldehydes was developed to prepare 3‐methyleneisoindolin‐1‐ones alkaloid . Kise and co‐workers recently reported electroreductive intramolecular coupling of phthalimides with aldehydes in the presence of TMS/TEA, thus generating fused isoindolobenzazepine alkaloids in good yields .…”

Tin(II) triflate Catalysed Synthesis of 3‐Methyleneisoindolin‐1‐ones

“…In another classical approach, organometallic reagents were added in phthalimides followed by subsequent dehydration afforded 3‐methyleneisoindolin‐1‐ones . Another approach developed for the preparation of 3‐methyleneisoindolin‐1‐ones was Horner reaction between phosphorylated isoindolinones and aryl aldehydes . In addition, Kise et al .…”