Advanced Methods for the Synthesis of 3-Substituted 1H-Isoindol-1-Ones

Abstract

The development of novel synthetic methods for the preparation of condensed aromatic and saturated isoindolones containing one or more heteroatoms is described and several new types of related ring systems are presented. The frequently applied N-acyliminium ion cyclization, the cyclocondensation of dicarbonyl compounds (e.g. γ-oxoacids) with amines and the photoinduced intramolecular ring-closure of N-substituted phthalimides are utilized in the syntheses. The enantioselective and diastereoselective procedures with the ratios of the isomers obtained are also discussed. R 1 , R 2 = H, Me, OH, CH 2 OH R 3 , R 4 = H, OMe Approaches to the Formation of Condensed Isoindolones

Scalable Synthesis of Interconnected Porous Silicon/Carbon Composites by the Rochow Reaction as High‐Performance Anodes of Lithium Ion Batteries

“…When the above conditions were applied to o ‐methoxycarbonyl sulfinamide 3Ea , isoindolinone 6Ea 27 was obtained by intramolecular cyclization reaction of initially formed amino ester 5Ea , which is presumably formed. Remarkably, this procedure to obtain ( R )‐3‐isopropylisoindolin‐1‐one has clear advantages with respect to existing procedures to prepare27,28 these compounds (of high potential both in asymmetric synthesis20c and in medicinal chemistry17), especially when these contain bulky alkyl groups at C‐3.…”

“…A particularly interesting group of (α‐phenylalkyl)amines contain ortho substituents like OH or OMe (with coordinating properties),15 CN16 or CO 2 R (as precursors of pharmacologically important isoindolin‐1‐ones)17 and halogens18 (susceptible to coupling, amidation or heteroatom addition reactions) 19. In particular, enantiomerically pure ortho ‐OH (or OMe) benzylamines and isoindolin‐1‐ones (readily obtained from ortho ‐CO 2 Me derivatives) with methyl groups at the benzyl position, have been used as chiral auxiliaries,20 ligands,21 or building blocks to prepare catalysts22 and biologically active compounds 23.…”

An Efficient, Three-Component Synthesis of Isoindolin-1-One-3-Phosphonates Under Mild and Solvent-Free Conditions and Their Biological Activities

“…For the synthesis of target compounds 4, we initially decided to explore the use of 2-formylbenzoic acid as starting material, considering its recent application in the synthesis of N-substituted isoindolin-1-one compounds [48][49][50][51][52][53][54][55][56][57][58]. Table 1: Isoindolin-1-one-3-phosphonantes 4a-f prepared Thus, the 'one-pot' three-component reaction of 2-formylbenzoic acid with a primary amine and diethylphosphite was stirred at 80 °C under solvent free-conditions, which generated the corresponding isoindolin-1-one-3-phosphonate 4a-f in 70-88% yield after 1 h ( Table 1).…”

A BF3-Mediated Nitrogen-to-Carbon Rearrangement of N-Protected 2,3-Dihydro-3-hydroxy-1H-benzisoindol-1-ones, and Its Interception for a Facile Preparation of 3-Substituted Benzisoindolones

“…26 Hence interception of the electrophilic intermediate 9 by an added nucleophile should permit the introduction of diverse groups at the 3-position while precluding re-attack of a-methylstyrene or 1,1-diphenylethylene. Given the large number of known 3-substituted isoindolones 27 and our interest in naphthyl-derived targets, we focused primarily on substitution of compounds 3b and 5b. A wide variety of common neutral carbon nucleophiles proved amenable for this chemistry.…”