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

Stajer, G.; Csende, Ferenc

doi:10.2174/1385272054863952

Cited by 32 publications

(8 citation statements)

References 53 publications

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“…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.…”

Section: Resultsmentioning

confidence: 99%

“…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.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2014

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Despite the promising application of porous Si‐based anodes in future Li ion batteries, the large‐scale synthesis of these materials is still a great challenge. A scalable synthesis of porous Si materials is presented by the Rochow reaction, which is commonly used to produce organosilane monomers for synthesizing organosilane products in chemical industry. Commercial Si microparticles reacted with gas CH3Cl over various Cu‐based catalyst particles to substantially create macropores within the unreacted Si accompanying with carbon deposition to generate porous Si/C composites. Taking advantage of the interconnected porous structure and conductive carbon‐coated layer after simple post treatment, these composites as anodes exhibit high reversible capacity and long cycle life. It is expected that by integrating the organosilane synthesis process and controlling reaction conditions, the manufacture of porous Si‐based anodes on an industrial scale is highly possible.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2014

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“…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).…”

Section: Resultsmentioning

confidence: 99%

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

Jelali

Nasr

Koko

et al. 2021

Preprint

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In this work, the synthesis of isoindolin-1-one-3-phosphonates by a ‘one-pot’ three-component reaction of 2-formylbenzoic acid with primary amines and dimethyl phosphite under solvent and catalyst free-conditions was reported. 1H NMR, 13C NMR, FT-IR and elemental analysis techniques, characterized the obtained compounds. The isoindolin-1-one-3-phosphonates were screened for their antimicrobial activities against bacteria and a fungus (Candida albicans). They were additionally also investigated for their anti-parasitical activities against Leishmania major promastigotes and amastigotes and Toxoplasma gondii in vitro. Cytotoxicity investigations of the isoindolin-1-one-3-phosphonates were led conducted in two human cancer cell lines, MDA-MB-231 and MCF-7and vero cells.

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“…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.…”

Section: Methodsmentioning

confidence: 99%

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

Schwan¹,

Duspara²,

Paquette³

et al. 2006

Synlett

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R e a r r a n g e m e n t o f N -P r o t e c t e d 2 , 3 -D i h y d r o -3 -h y d r o x y -1 H -b e n z i s o i n d o l -1 -o n e sAbstract: A BF 3 -mediated release of the hydroxy and the nitrogenprotecting group of N-(cumyl or 1,1-diphenylethyl)-2,3-dihydro-3-hydroxy-1H-benzisoindol-1-ones is accompanied by recombination of the nitrogen-protecting unit to the 3-position of the ring system. The addition of sulfur or carbon nucleophiles affords products of preferential capture of the rearrangement intermediate offering a convenient and rapid synthetic route to N-unprotected 2,3-dihydro-3-substituted-1H-benzisoindol-1-ones.The naphthyl amide organic fragment is prevalent in a number of bioactive compounds 1-6 including those targeting the NK1 receptor, 1 the inhibition of aldosterone synthase, 3 the leukocyte proteases cathepsin G 4 and chymase, 5 and a malarial receptor. 2 Aromatic amides including some naphthyl amides are also central to the inhibition of a group of poly(ADP-ribose) polymerase enzymes (PARPs) 7-9 that bind NAD + and have been implicated in the cellular response to DNA injury. 10 The catalytic domain of the PARP enzymes has been shown to be structurally similar to that of bacterial ribosyltransferases, including Pseudomonas aeruginosa exotoxin A, which we are currently studying. PARP inhibitors often contain aromatic amide or lactam functionalities and operate by preferentially binding to the nicotinamide portion of the binding pocket normally occupied by NAD + . 9,11,12 As such, we have targeted novel amides and imides possessing the naphthalene 11 backbone as part of a study to find inhibitors of exotoxin A.Specifically, we have been probing the functionalization of the 2-position of N-protected 1-naphthamides. We applied the Dai protocol for the ortho-metalation of N,Ndisubstituted amides (3.2 equiv s-BuLi, THF, -78°C, 3 h) 13 to monosubstituted amides 1 (a: R = 1,1-diphenylethyl, b: R = cumyl) as a means to introduce additional functionality. Consistent with the literature, 14 the metalation proceeds at the 2-position rather than the 8-position giving dianions 2. Quenching with DMF affords two naphthalimidines (2,3-dihydro-3-hydroxy-1H-benz[e]isoindol-1-ones, 3), which differ only by their protection on the nitrogen (Scheme 1). At this point, nitrogen deprotection was attempted with BF 3 ·OEt 2 15 and a surprising yet parallel manifold of products was obtained for both compounds 3a and 3b. Scheme 2 and the first two entries of Table 1 indicate the assigned structures of the unexpected products. In each product, the nitrogen-protecting group is apparently lost and its carbon skeleton is reattached at the adjacent carbon atom. 16 Scheme 1Three more substrates were prepared in order to establish the generality of the rearrangement. Application of the Dai metalation conditions to the appropriate N-1,1-diphenylethyl and N-cumyl amides gave phthalimidines (2,3-dihydro-3-hydroxy-1H-isoindol-1-ones) 4a (79%) and 4b 15 (67%), respectively, and 3-hydroxy-2,3-dihydro-1H-benz[f]isoindol-1-one (5b, 50%, T...

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

Cited by 32 publications

References 53 publications

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

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

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

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

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

Cited by 32 publications

References 53 publications

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

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

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

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

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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