19803-10-2

Upstream product

• 16188-57-1 2-iodo-4-methylphenol 
• 84384-30-5 4-(4-methoxyphenyl)-2-methyl-3-butyn-2-ol 
• 5720-07-0 4-methoxyphenylboronic acid 
• 123389-03-7 (E)-1-(1,2-dichlorovinyloxy)-4-methylbenzene 
• 768-60-5 4-methoxyphenylacetylen 
• 4383-07-7 2-hydroxymethyl-4-methylphenol 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 1452849-98-7 5-methyl-2-hydroxybenzyltriphenylphosphonium bromide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 6627-55-0 2-bromo-p-cresol 
• 106-44-5 p-cresol 
• 1313886-73-5 2-((4-methoxyphenyl)ethynyl)-4-methylphenyl acetate 

Downstream Products

• 1260505-22-3 (2-bromo-4,5-difluorophenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-23-4 (4-hydroxyphenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-26-7 (4-hydroxy-3-methylphenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-28-9 (4-hydroxy-3-iodophenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-21-2 (3,5-dichlorophenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1313886-74-6 (2-hydroxy-3-methoxyphenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-24-5 (3-hydroxy-5-methoxyphenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-15-4 (3,4,5-trimethoxyphenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-19-8 (4-chlorophenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-13-2 (4-methoxyphenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-20-1 (2-bromophenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-14-3 (3,5-dimethoxyphenyl)(2-(4-methoxy-phenyl)-5-methylbenzofuran-3-yl)methanone 
• 1260505-16-5 (2,3-dimethoxyphenyl)(2-(4-methoxyphenyl)-5-methylbenzofuran-3-yl)methanone 

Relevant academic research and scientific papers

A new synthesis of 2-aryl/alkylbenzofurans by visible light stimulated intermolecular Sonogashira coupling and cyclization reaction in water

A visible light induced rapid one pot intermolecular Sonogashira coupling and 5-endo-dig cyclization in water of ortho-halophenols and terminal alkynes catalyzed by [Pd] have been developed to furnish 2-aryl/alkyl benzofurans in good yields sans Ru or Ir

CuI catalyzed domino coupling–cyclization of 2-iodo-phenols and 1-alkynes to the synthesis of 2-substituted benzo[b]furans/furo-pyridines

CuI/proline-catalyzed coupling reaction of 2-iodo-phenols with terminal alkynes and the following cyclization process is carried out successively in DMSO at 80 °C. Under this tandem process, 2-substituted benzo[b]furans/furo-pyridines were synthesized in good to excellent yields with a great diversity.

Preparation method of multi-substituted benzofuran derivative

The invention provides a preparation method of a multi-substituted benzofuran derivative. The multi-substituted benzofuran derivative is obtained by taking end alkyne and a halogenated phenol derivative as starting raw materials, copper salt as a catalyst and amino acid as an additive and performing coupling reaction in an organic solvent under the condition of adding alkali, wherein the catalystis CuX, X is iodine or bromine, the molar ratio of the catalyst to the halogenated phenol derivative is (0.001-0.5):1, the molar ratio of the amino acid to the catalyst is (0.1-3):1, the molar ratio of the halogenated phenol derivative to the end alkyne is (1-1.5):1, and the reaction temperature is 30 to 150 DEG C. An expensive palladium catalyst liable to cause environmental pollution is not used. The method is simple in process and high in operability, and has a good industrial application prospect.

2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: Synthesis, biological activity and molecular modeling

A series of 2-phenylbenzofurans compounds was designed, synthesized and evaluated as cholinesterase inhibitors. The biological assay experiments showed that most of the compounds displayed a clearly selective inhibition for butyrylcholinesterase (BChE), while a weak or no effect towards acetylcholinesterase (AChE) was detected. Among these benzofuran derivatives, compound 16 exhibited the highest BChE inhibition with an IC50 value of 30.3 μM. This compound was found to be a mixed-type inhibitor as determined by kinetic analysis. Moreover, molecular dynamics simulations revealed that compound 16 binds to both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of BChE and it displayed the best interaction energy value, in agreement with our experimental data.

Fluorination of 2-substituted benzo[b]furans with Selectfluor

An efficient protocol was developed to access 3-fluoro-2-hydroxy-2-substituted benzo[b]furans with Selectfluor as the fluorinating reagent in MeCN and water. By utilizing SOCl2/Py as the dehydrating agent, the compounds above were readily conve

MAO Inhibitory Activity of 2-Arylbenzofurans versus 3-Arylcoumarins: Synthesis, invitro Study, and Docking Calculations

Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Several 3-arylcoumarin derivatives were previously described as interesting selective MAO-B inhibitors. Preserving the trans-stilbene structure, a series of 2-arylbenzofuran and corresponding 3-arylcoumarin derivatives were synthesized and evaluated as inhibitors of both MAO isoforms, MAO-A and MAO-B. In general, both types of derivatives were found to be selective MAO-B inhibitors, with IC50 values in the nano- to micromolar range. 5-Nitro-2-(4-methoxyphenyl)benzofuran (8) is the most active compound of the benzofuran series, presenting MAO-B selectivity and reversible inhibition (IC50=140nM). 3-(4′-Methoxyphenyl)-6-nitrocoumarin (15), with the same substitution pattern as that of compound 8, was found to be the most active MAO-B inhibitor of the coumarin series (IC50=3nM). However, 3-phenylcoumarin 14 showed activity in the same range (IC50=6nM), is reversible, and also severalfold more selective than compound 15. Docking experiments for the most active compounds into the MAO-B and MAO-A binding pockets highlighted different interactions between the derivative classes (2-arylbenzofurans and 3-arylcoumarins), and provided new information about the enzyme-inhibitor interaction and the potential therapeutic application of these scaffolds.

Synthesis and antimicrobial evaluation of new benzofuran derivatives

Thirteen compounds, based on benzofuran skeleton bearing aryl substituents at its C-3 position through methanone linker, were synthesized and screened for their antibacterial and antifungal activities against four bacteria Escherichia coli, Staphylococcus aureus, Methicillin-resistant S. aureus, Bacillus subtilis, and a fungus Candida albicans. Four hydrophobic benzofuran analogs were found to exhibit favorable antibacterial activities (MIC80 = 0.39-3.12 μg/mL), which were better than the control drugs.

Microwave-assisted efficient synthesis of 2-arylbenzo[b]furans and 2-ferrocenylbenzo[b]furans from readily prepared propargylic alcohols and o-iodophenols

A simple, efficient and expeditious method for synthesis of 2-arylbenzo[b]furans and 2- ferrocenylbenzo[b]furans from readily prepared propargylic alcohols, o-iodophenols and silica gel with the catalyst of PdCl2(PPh3)2 (2 mol%)/CuI (2mol%) and microwave-promoted Sonogashira coupling/cyclization reaction is developed. The methodology can produce good to excellent yields. In addition, this method can also be completed in one-pot with iodobenzene, 2-methyl-3-butyn-2-ol and 2-iodo-4-methylphenol as reactants. Indian Academy of Sciences.

2-substituted benzo[b]furans from (E)-1,2-dichlorovinyl ethers and organoboron reagents: Scope and mechanistic investigations into the one-pot Suzuki coupling/direct arylation

2-Substituted benzo[b]furans can easily be assembled from simple phenols, boronic acids or other organoboron reagents, and trichloroethylene. The overall process requires only two synthetic steps, with the key step being a one-pot sequential Suzuki cross-coupling/direct arylation reaction. The method tolerates many useful functional groups and does not require the installation of any other activating functionality. The modular nature of the process permits the rapid synthesis of many analogues using essentially the same chemistry, of particular value in drug development. Results of kinetic isotope effect studies and investigations into the regioselectivity of the process indicate that the direct arylation step most likely does not involve an electrophilic palladation. The most likely mechanism lies somewhere on the continuum between a C-H bond metathesis and an assisted palladation or concerted metallation-deprotonation pathway. A very efficient modular approach to the construction of benzo[b]furans using trichloroethylene as a scaffold is described. This method gives easy access to highlysubstituted heterocycles in only two synthetic operations, and is especially suitable for rapid construction of compound libraries.

Simple, convenient, and efficient synthesis of 2-aryl-substituted benzo[b]furans

A simple, convenient, and efficient one-pot method for the preparation of benzofuran is reported. Sonogashira coupling reaction of aryl iodides with 2-methyl-3-butyn-2-ol was used as an acetylene source in the presence of Pd(PPh3)2Cl2 and CuI. Deprotection of the acetylene moiety in the same pot using a strong base and the second Sonogashira coupling/cyclization of and substituted o-iodophenols led to the formation of the appropriate benzo[b]furans. These protocols also can be used in the synthesis of natural products and indoles. Copyright Taylor & Francis Group, LLC.