62827-72-9

Upstream product

• 118520-71-1 2-(2-(4-chlorophenyl)ethynyl)benzoic acid methyl ester 
• 92428-45-0 2-(4'-chlorobenzoyl)methylbenzoic acid 
• 89-51-0 Homophthalic acid 
• 122-01-0 4-chloro-benzoyl chloride 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 74-11-3 para-chlorobenzoic acid 
• 1127955-67-2 2-(2-bromophenyl)-1-(4-chlorophenyl)ethanone 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 18931-60-7 1-(4-chlorophenyl)-4,4,4-trifluorobutane-1,3-dione 
• 873-73-4 4-n-chlorophenylacetylene 
• 124-38-9 carbon dioxide 
• 1864-94-4 phenyl formate 
• 88-67-5 2-Iodobenzoic acid 
• 18362-49-7 1,3-bis(4-chlorophenyl)propane-1,3-dione 

Downstream Products

• 92428-45-0 2-(4'-chlorobenzoyl)methylbenzoic acid 
• 92429-97-5 3-(4-chlorophenyl)-1H-isochromene-1-thione 
• 38453-86-0 1-(4-chlorophenyl)-2-[2-(hydroxymethyl)phenyl]ethanol 
• 1138559-19-9 2-(2-benzoylphenyl)-1-(4-chlorophenyl)ethanone 
• 92874-01-6 methyl 2-(2-(4-chlorophenyl)-2-oxoethyl) benzoate 
• 38453-75-7 3-(4-chlorophenyl)-3,4-dihydro-1H-isochromen-1-one 

Relevant academic research and scientific papers

Modular synthesis of 3-substituted isocoumarinsviasilver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes

A method involving silver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes to yield 3-substituted isocoumarins is described. The developed protocol allows convenient access to a range of synthetically useful 3-substituted isocoumarins and related fused heterocyclolactones in good to high yields, using silver tetrafluoroborate as the catalyst, and atmospheric oxygen as the terminal oxidant and the source of endocyclic oxygen. Mechanistic studies suggest the involvement of a free-radical pathway.

p-TSA-Based DESs as “Active Green Solvents” for Microwave Enhanced Cyclization of 2-Alkynyl-(hetero)-arylcarboxylates: an Alternative Access to 6-Substituted 3,4-Fused 2-Pyranones

In this paper, we describe the use of p-TSA based Deep Eutectic Solvents (DESs) as alternative environmental-friendly “active” solvents for the microwave-mediated synthesis of 6-substituted 3,4-fused 2-pyranones, and in particular isocoumarins, starting from 2-alkynyl-(hetero)arylcarboxylates. When the alkyne terminus bears a neutral or an electron-donating group (EDG), the reactions are fast, clean and highly regioselective, to give the 6-endo-dig cyclization products in good to excellent yields. For substrates bearing an electron-withdrawing group (EWG) on the alkyne end, the regioselectivity can be tuned by adding a small amount of silver(I) triflate as co-catalyst. DES was demonstrated to be reusable without loss of efficiency in terms of reaction yields. Based on experimental evidence and previous findings, two competitive mechanisms working simultaneously are proposed to explain the outcomes and the regioselectivity issues.

Sulfoxonium Ylides as Carbene Precursors: Rhodium(III)-Catalyzed Sequential C?H Functionalization, Selective Enol Oxygen-Atom Nucleophilic Addition, and Hydrolysis

Herein, we report a protocol for Rh(III)-catalyzed annulation reactions between oxazolines and sulfoxonium ylides via a sequence involving C?H activation, selective enol oxygen-atom nucleophilic addition, and hydrolysis. This practical, operationally simple protocol has a wide substrate range, excellent regioselectivity, and moderate to good yields.

Fluorination-triggered tandem cyclization of styrene-type carboxylic acids to access 3-aryl isocoumarin derivatives under microwave irradiation

A practical and straightforward synthetic route through a fluorination-triggered tandem cyclization of styrene-type carboxylic acids was developed to construct a variety of 4-fluoro-3-aryl-3,4-dihydroisocoumarins and 3-arylisocoumarins under microwave irr

Silver triflate/: P -TSA co-catalysed synthesis of 3-substituted isocoumarins from 2-alkynylbenzoates

In this paper, we describe the silver triflate/p-toluenesulfonic acid co-catalysed synthesis of seventeen isocoumarins and two thieno[2,3-c]pyran-7-ones starting from 2-alkynylbenzoates and 3-alkynylthiophene-2-carboxylates, respectively. The reaction proceeds with absolute regioselectivity under mild reaction conditions and low catalyst loading, to afford the desired products in good to excellent yields. A conceivable reaction mechanism is proposed and supported by isotope-exchange tests, 1H NMR studies and ad hoc experiments.

Preparation method of isocoumarin medicament intermediate

The invention relates to a preparation method of an isocoumarin medicament intermediate as shown in the following formula (5). The method has a reaction route as follows, and the method comprises thefollowing steps: S1: a compound in a formula (1) and a compound in a formula (2) are reacted under the existence of a palladium catalyst, a cationic ammonium compound, and alkali in an organic solvent, after the reaction ends, aftertreatment is carried out, in order to obtain a compound in a formula (3); S2: in an organic solvent, under the existence of an oxidizing agent, a self cyclization reaction of the compound in the formula (3) is carried out, and after the reaction ends, aftertreatment is carried out in order to obtain a compound in a formula (4); S3: under the existence of the palladium compound catalyst and the acidic compound, in a solvent, a reaction is carried out for the compound in the formula (4), and after the reaction ends, aftertreatment is carried out in order to obtainthe isocoumarin medicament intermediate as shown in the formula (5). According to the method, multiple technical characteristics of each step can be subjected to creative optimization, a whole new synthetic method and synthetic route is provided for preparing the isocoumarin compound, and the method has good industrialization prospect and latent application values.

Medical intermediate diaryl ethylene oxide compound and synthesis method thereof

The invention relates to a medical intermediate namely a diaryl ethylene oxide compound shown by the formula (I) as shown in the specification and a synthesis method thereof, wherein R1 is selected from H, halogen or C1-C6 alkyl; and R2 is selected from H, halogen, C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkyl or halogenated C1-C6 alkoxy. The invention also relates to a synthesis method of the derivative. The diaryl ethylene oxide compound can be used for one-step synthesis of isocoumarin compounds, thus having good application prospect and research value in the field of synthesis of theisocoumarin compounds.

Synthetic method of isocoumarin medicament intermediate

The invention relates to a synthetic method of an isocoumarin medicament intermediate as shown in the following formula (I). The method comprises the following steps: under existence of a palladium compound catalyst and an acidic compound, in a solvent, a reaction is carried out for a compound as shown in the following formula (II), after the reaction ends, an isocoumarin medicament intermediate as shown in the formula (I) is obtained, wherein R1 is selected from H, halogen, or C1-C6 alkyls; R2 is selected from H, halogen, C1-C6 alkyls, C1-C6 alkoxys, halogenated C1-C6 alkyls or halogenated C1-C6 alkoxys. The method employs specific catalysts, acidic compounds and solvents, in order to provide good technical effects. The invention also provides a novel synthetic method of the compound in the formula (II) as a reactant, in order to provide a simple preparation method for synthesis of the isocoumarin medicament intermediate, and the method has good application prospects and research values.

Palladium-Catalyzed Sequential Nucleophilic Addition/Oxidative Annulation of Bromoalkynes with Benzoic Acids to Construct Functionalized Isocoumarins

An efficient and robust protocol for the preparation of 3-substituted isocoumarins via palladium-catalyzed nucleophilic addition/oxidative annulation of bromoalkynes with benzoic acids has been developed. Remarkably, preliminary mechanistic studies indicated that the transformation might proceed via a stereo- and regioselective nucleophilic addition and C-H functionalization procedure.

Pd-Catalyzed/Iodide-Promoted α-Arylation of Ketones for the Regioselective Synthesis of Isocoumarins

A variety of isocoumarins have been synthesized directly from 2-halobenzoates and ketones through a palladium-catalyzed α-arylation step followed by an intramolecular cyclization process. The addition of iodide anions to the reaction mixture increased yields and selectivities especially when 2-bromobenzoates were employed. This phosphine-free one-pot synthesis features a high functional group tolerance and gives access to richly decorated isocoumarins. This general methodology was successful in the total synthesis of Xyridin A, an important natural product with antibacterial and antifungal activity.