39142-91-1

Upstream product

• 5194-48-9 α-oxo-bibenzyl-2-carboxylic acid amide 
• 40523-32-8 3-(phenylmethylene)isoindol-1-one 
• 342608-09-7 3-benzyl-2-(dimethylamino)-2,3-dihydro-1H-isoindol-1-one 
• 20871-31-2 2,3-dihydro-3-hydroxy-3-(phenylmethyl)-1H-isoindol-1-one 
• 136918-14-4 phthalimide 
• 1589-82-8 phenylmagnesium bromide 
• 85-44-9 phthalic anhydride 
• 4770-30-3 2-(dimethylamino)isoindoline-1,3-dione 
• 287199-38-6 2-(dimethylamino)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one 
• 80221-08-5 2-(2-phenylethynyl)benzamide 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 100-42-5 styrene 
• 60901-21-5 o-styrylbenzoic acid 
• 63404-82-0 (E)-2-styrylbenzamide 

Downstream Products

• 1012068-67-5 7-benzyl-12-methoxycarbonylisoindolo[2,1-b]isoquinolin-5-one 

Relevant academic research and scientific papers

Corrigendum: Rhodium(III) Complex with a Bulky Cyclopentadienyl Ligand as a Catalyst for Regioselective Synthesis of Dihydroisoquinolones through C?H Activation of Arylhydroxamic Acids (Chemistry – A European Journal, (2018), 24, (16570–16575), 10.1002/chem.201804050)

In the original article, Scheme 5 describes the reaction of O-Boc-phenylhydroxamic acid with a mixture of alkenes, Scheme 6 describes the reaction of O-Boc- and O-Piv-phenylhydroxamic acid with styrene. Both schemes show the formation of the product 4 p, which was erroneously assigned as 4-phenyl-3,4-dihydroisoquinolinone, based on the previous literature report.[1] Recently, S.-L. You et al. and H. Waldmann et al. have independently discovered that 4 p has in fact the structure of 3-benzylisoindolin-1-one (this was confirmed by X-ray structures of chloro-substituted derivatives).[2, 3] Therefore, we provide the corrected Schemes 5 and 6 and the corresponding text for our article as shown below. The yields and selectivities remain the same. We apologize for any inconvenience caused by the previous incorrect assignment. Recently, another paper with the incorrect assignment of 4 p has been corrected in a similar manner.[4] Corrected description for the Scheme 5. The difference in reactivity of alkenes creates the opportunity of chemoselective reactions. For example, reaction of 1 a with an equimolar mixture of allyl alcohol, styrene and myrcene proceed selectively in the presence of the catalyst 5 to give 4-CH2OH-substituted product 4 e in 89 % yield (Scheme 5). Similar reaction in the presence of the classical catalyst [Cp*RhCl2]2 gave a mixture of three products: 3-benzylisoindolin-1-one 4 p, as well as two CH2OH-substituted isomers 4 e and 3 e in 1.7:1:2.5 ratio (note that myrcene did not react in both cases). 5 Scheme (Figure presented.) Chemoselectivity of reaction of 1 a with a mixture of alkenes. Corrected description for the Scheme 6. Additionally, as it was noted by Corminboeuf and Cramer et al., (References [14, 17] in the original publication) the steric interactions between the cyclopentadienyl ligand and the Boc group are important for selectivity. Indeed, we observed that the reaction of O-Boc-phenylhydroxamic acid 1 a with styrene in the presence of the classical catalyst [Cp*RhCl2]2 gives only the 3-benzylisoindolin-1-one 4 p, while similar reaction of O-pivaloyl-phenylhydroxamic acid 1 b produced the 3-substituted structural isomer 3 p (Scheme 6). The reasons for this striking difference are not fully clear. Unfortunately, both reactions in the presence of the catalyst 5 proceeded slowly and gave mixtures of product. 6 Scheme (Figure presented.) Regioselectivity determined by Boc- or pivalyl group of hydroxamic acid derivative.

RhIII-Catalyzed C?H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones

RhIII-catalyzed C?H functionalization reaction yielding isoindolinones from aryl hydroxamates and ortho-substituted styrenes is reported. The reaction proceeds smoothly under mild conditions at room temperature, and tolerates a range of functional groups. Experimental and computational investigations support that the high regioselectivity observed for these substrates results from the presence of an ortho-substituent embedded in the styrene. The resulting isoindolinones are valuable building blocks for the synthesis of bioactive compounds. They provide easy access to the natural-product-like compounds, isoindolobenzazepines, in a one-pot two-step reaction. Selected isoindolinones inhibited Hedgehog (Hh)-dependent differentiation of multipotent murine mesenchymal progenitor stem cells into osteoblasts.

COMPOUND HAVING BET INHIBITORY ACTIVITY AND PREPARATION METHOD AND USE THEREFOR

The invention relates to the field of pharmaceutical chemistry. Specifically, the present invention relates to a series of BET (bromodomain and extra-terminal domain) inhibitors having a novel structure, particularly inhibitors targeting BRD4 (Bromodomain-containing protein 4), and a preparation method and use therefor. The structure thereof is shown in the following general formula (I). Said compounds or a stereoisomer, racemate, geometric isomer, tautomer, prodrug, hydrate, solvate, or crystal form thereof, or a pharmaceutically acceptable salt thereof, and the pharmaceutical compsosition thereof can be used for the treatment and/or prevention of related diseases mediated by bromodomain proteins.

Corrigendum to: Ligand-Controlled Regiodivergent Pathways of Rhodium(III)-Catalyzed Dihydroisoquinolone Synthesis: Experimental and Computational Studies of Different Cyclopentadienyl Ligands (Chemistry - A European Journal, (2014), 20, 47, (15409-15418), 10.1002/chem.201404515)

The authors became aware that product 4aa was erroneously assigned to 4-phenyl- 3,4-dihydroisoquinolin-1(2H)-one. Reanalysis of the 1H NMR and 13C NMR spectra of product 4aa confirmed that the correct structure corresponds to the constitutional 3-benzyl-isoindolones isomer (Figure 1). 4-Phenyl-3,4-dihydroisoquinolin-1(2H)-one was reported by Ellman and its structure was confirmed by X-ray crystallographic analysis.[1] The corrected isoindolone structure of 4aa matches all data of 3-benzylisoindolone synthesized by a different route.[2]. (Figure presented.).

Synthesis of Lactams via Ir-Catalyzed C-H Amidation Involving Ir-Nitrene Intermediates

x-membered lactams were synthesized via either an amidation of sp3 C-H bonds or an electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.

Highly stereoselective synthesis of (Z)-3-methoxy-1-methyleneisoindoles via DMAP catalyzed cyclization of methyl 2-alkynylbenzimidates

A DMAP (4-dimethylaminopyridine) catalyzed cyclization of methyl 2-alkynylbenzimidates has been developed, which affords 3-methoxy-1-methyleneisoindoles with excellent Z-stereoselectivity under mild and transition-metal-free conditions. The (Z)-3-methoxy-

Intramolecular Hydroamidation of ortho-Vinyl Benzamides Promoted by Potassium tert-Butoxide/N,N-Dimethylformamide

An intramolecular hydroamidation of ortho-vinyl benzamides had been developed. The reaction was promoted efficiently by potassium tert-butoxide and N,N-dimethylformamide without the need for strong oxidants or transition-metal catalysts. A series of dihyd

Synthesis of Isoindolinones by Pd-Catalyzed Coupling between N-Methoxybenzamide and Styrene Derivatives

An atom-economical protocol for a tandem process involving Fujiwara-Moritani-aza-Wacker reactions has been developed for the Pd-catalyzed coupling between N-methoxy benzamide and styrene derivatives. The generality of the methodology was demonstrated by the synthesis of a library of 25 3-benzylidene isoindolinones in moderate to good yields. A further 40 3-benzyl derivatives were obtained by telescoping the process with a catalytic hydrogenation reaction.

Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones

Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones, was developed using chiral phosphoric acid as catalyst and a Hantzsch ester as the hydrogen source with up to 95% ee. The reaction process of this asymmetric

A Practical Two-Step Synthesis of 3-Alkyl-2,3-dihydro-1H-isoindolin-1-ones

A flexible approach to 3-alkyl-2,3-dihydro-1H-isoindolin-1-ones via the reductive-alkylation procedure is described. Present method is versatile in scope, allowing the easy introduction of various C-3 carbon-substituents by Grignard addition to phthalimid