Heterocyclic Building Block-benzofuran

Paymode, Dinesh J. published the artcileStudies toward the Total Synthesis of Parvifolals A/B: An Intramolecular o-Quinone Methide [4 + 2]-Cycloaddition To Construct the Central Tetracyclic Core, Category: benzofurans, the main research area is parvifolol tetracyclic core preparation cycloaddition.

Two different approaches comprising the intramol. [4+2]-cycloaddition of in situ generated o-quinone methides (o-QMs) have been explored to construct the central tetracyclic core of parvifolols A/B. At the outset, a cross-pinacol coupling of 2-formyl-tri-O-Methylresveratrol with 4-methoxysalicylaldehyde followed by acid treatment were found to provide the desired tetracyclic core (I) with an internal olefin. The requisite pendant aryl group has been introduced by a Pd-catalyzed direct coupling of corresponding diazonium salt.

ACS Omega published new progress about [4+2] Cycloaddition reaction. 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, Category: benzofurans.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Kubeczka, K. H. published the artcileThe compositions of the essential root oils from Pimpinella saxifraga s.l. and chemotaxonomic implications, HPLC of Formula: 13391-27-0, the main research area is Pimpinella root oil composition chemotaxonomy; sesquiterpene Pimpinella root oil chemotaxonomy.

The essential root oils of the P. saxifraga subspecies eusaxifraga, alpestris and nigra were investigated by means of capillary GC and spectroscopic methods. A total of 48 components was identified. Characteristic constituents of all oils are pseudoisoeugenol derivatives, sesquiterpenoids and trinor-sesquiterpene hydrocarbons, but the qual. and quant. patterns of the individual oils exhibit significant differences. The results obtained were discussed in regard to a chemotaxonomic reliable delimitation of the 3 described subspecies of P. saxifraga.

Zeitschrift fuer Naturforschung, C: Journal of Biosciences published new progress about Pimpinella saxifraga alpestris. 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, HPLC of Formula: 13391-27-0.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Okuyama, Tadashi published the artcileSubstituent effects in the benzofuran system. I. Proton and carbon-13 chemical shifts, Name: 6-Methoxybenzofuran, the main research area is NMR benzofuran substituent effect.

PMR and 13C NMR spectra of benzofuran and its derivatives (2-Me, 3-Me, 5-Me, 6-Me, 5-MeO, 6-MeO, 5-Cl) have been measured. The chem. shifts of 2-H and 2-C of 5- and 6-substituted derivatives obeyed a modified Hammett equation, δ = ρ1σ1 + ρ2σ2 +δ0. Electronic effects were transmitted mainly through the bond 8-3. The ground state electronic structure was similar to that of styrene rather than phenyl vinyl ether.

Bulletin of the Chemical Society of Japan published new progress about Linear free energy relationship. 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, Name: 6-Methoxybenzofuran.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Boykin, David W. published the artcileOxygen-17 nuclear magnetic resonance spectroscopic study of substituted phthalic anhydrides and phthalides, Category: benzofurans, the main research area is NMR oxygen phthalic anhydride phthalide.

17O chem. shift data (natural abundance) for 3-substituted phthalic anhydrides and 4- and 7-substituted phthalides in acetonitrile at 75° are reported. Steric interactions of substituents ortho to the carbonyl groups result in deshielding effects (9-22 ppm) relative to parent compounds regardless of the electronic character of the substituents. Factors contributing to the deshielding effects are discussed. The relationship between 17O chem. shifts and regiochem. of the phthalic anhydrides is discussed.

Canadian Journal of Chemistry published new progress about NMR (nuclear magnetic resonance). 52010-22-7 belongs to class benzofurans, name is 4-Chlorophthalide, and the molecular formula is C8H5ClO2, Category: benzofurans.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Cao, Jun published the artcilePalladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N’-Acyl Arylhydrazines, Recommanded Product: 6-Methoxybenzofuran, the main research area is benzofuran acyl arylhydrazine palladium catalyst TEMPO regioselective arylation; arylbenzofuran preparation.

A novel ligand-free palladium-catalyzed C-2 arylation of benzofurans has been developed using N’-acyl arylhydrazines as the coupling partners and TEMPO as an oxidant. This protocol features a wide functional-group tolerance and highly regioselective products with good to excellent yields.

European Journal of Organic Chemistry published new progress about Arylation catalysts (regioselective). 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, Recommanded Product: 6-Methoxybenzofuran.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Menkir, Mengistu Gemech published the artcileThe role of cesium fluoride in aryl propargyl ether Claisen rearrangement and its mechanistic elucidation: a theoretical study, Formula: C10H10O2, the main research area is cesium fluoride aryl propargyl ether Claisen rearrangement mechanistic theor.

The role of cesium fluoride (CsF) in aryl propargyl ether Claisen rearrangement and its mechanistic pathway were studied in gas and solvent phase using the d. functional theory implemented in Gaussian 09. Results indicate that the [3,3]-sigmatropic rearrangement is the rate-limiting step with ΔG‡ value of 37.1 kcal/mol in solvent phase. Also, the enolization of α-allenylketone intermediate (Int1-CsF) has a higher free energy barrier, which implies that the formation of benzopyran is not favored in the presence of CsF. However, the abstraction of the α-hydrogen atom in Int1-CsF with CsF shows a very low free energy barrier and is the most favored pathway for aryl propargyl ether Claisen rearrangement in the presence of CsF to form benzofuran. In the case of substituted aryl propargyl ethers, a methoxy group on the benzene ring lowers the activation barrier. The HOMO-LUMO, conformational and NBO anal. indicate that increasing Me substitution on the propargyl residue enhances the rearrangement reaction.

Structural Chemistry published new progress about [3,3]-Sigmatropic rearrangement (rds). 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Formula: C10H10O2.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Ueno, Atsushi published the artcileCopper-Catalyzed Formal C-H Carboxylation of Aromatic Compounds with Carbon Dioxide through Arylaluminum Intermediates, Safety of 6-Methoxybenzofuran, the main research area is aryl carboxylic acid regioselective preparation; aromatic compound alkyl amido lithium aluminate deprotonative alumination; carbon dioxide arylaluminum carboxylation copper catalyst; aromatic compounds; carbene ligands; carbon dioxide; carboxylation; copper.

The C-H bond carboxylation of various aromatic compounds with CO2 was achieved by the deprotonative alumination with a mixed alkyl amido lithium aluminate compound iBu3Al(TMP)Li followed by the NHC-copper-catalyzed carboxylation of the resulting arylaluminum species, which afforded the corresponding carboxylation products in high yield and high selectivity. In addition to benzene derivatives, heteroarenes such as benzofuran, benzothiophene, and indole derivatives are also suitable substrates. Functional groups such as Cl, Br, I, vinyl, amide, and CN could survive the reaction conditions. Some key reaction intermediates such as the copper aryl and iso-Bu complexes and their carboxylation products were isolated and structurally characterized by X-ray crystallog. analyses, thus offering important information on the reaction mechanism.

Chemistry – An Asian Journal published new progress about Alumination (deprotonative, regioselective). 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, Safety of 6-Methoxybenzofuran.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Liu, Bin published the artcileSynthesis of 1,2-phenylenedimethanols by base-promoted reduction of isobenzofuran-1(3H)-ones with silane, Computed Properties of 52010-22-7, the main research area is phenylenedimethanol preparation isobenzofuranone reduction base silane.

An efficient method for preparation of substituted 1,2-phenylenedimethanols and aliphatic 1,4-diols that are valuable intermediates in organic synthesis, was developed by the base-promoted reduction of isobenzofuran-1(3H)-ones and γ-lactones with silane under mild conditions. Compared with traditional procedures using stoichiometric amounts of metal hydrides and alkyl reductants, the present method avoids the use of sensitive reagents and is operationally simple and a broad variety of functional groups are tolerated.

Chinese Chemical Letters published new progress about Bases Role: RGT (Reagent), RACT (Reactant or Reagent). 52010-22-7 belongs to class benzofurans, name is 4-Chlorophthalide, and the molecular formula is C8H5ClO2, Computed Properties of 52010-22-7.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Anderson, Wayne K. published the artcileUse of 2,3-dichloropropene and 1,3-dichlorobut-2-ene as synthons for heterocyclic compounds. Synthesis of 2-methylbenzo[b]furans, 2-methylbenzo[b]thiophenes, and 4-methyl-2H-chromene, Category: benzofurans, the main research area is phenol condensation chloro alkene; thiophenol condensation chloro alkene; cyclization propene arylthio chloro; Claisen rearrangement aryloxychloropropene; benzofuran methyl; benzothiophene methyl; chromene methyl.

Addnl. data considered in indexing and abstracting are available from a source cited in the original document. The ethers I (X = O, R = H, p-Me, p-OMe, p-Cl, o-Me, o-OMe, o-Cl), prepared by condensation of the appropriate phenol with CH2:CClCH2Cl (II), underwent Claisen rearrangement to give the phenols III, acid-catalyzed cyclization of which gave 28-77% benzofurans IV (X = O). The thio ether I (X = S, R = H, p-Me, p-OMe, p-Cl, o-Me), similarly prepared from the appropriate thiophenol and II, cyclized directly on heating in PhNEt2 to give 54-80% benzothiophenes IV (X = S). Condensation of PhOH with MeCCl:CHCH2Cl gave 78% 3-chloro-1-phenoxybut-2-ene, which thermally cyclized to give 64% 4-methyl-2H-chromene.

Journal of the Chemical Society, Perkin Transactions 2: Organic and Bio-Organic Chemistry published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Category: benzofurans.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Zhou, Muxing published the artcileChiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters, Computed Properties of 52010-22-7, the main research area is acylative dynamic kinetic resolution hydroxyphthalide bicyclic imidazole catalyst; enantioselective acylation hydroxyphthalide dynamic kinetic resolution; phthalidyl ester prodrug preparation acylative dynamic kinetic resolution; bicyclic imidazole; dynamic kinetic resolution; enantioselective acylation; organocatalyst; phthalidyl ester prodrugs.

Utilizing a chiral bicyclic imidazole organocatalyst, I, and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99% ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure anal. of the key transition states shows that the CH-π interaction, and not the previously considered cation/π-π interactions between the catalyst and substrate, is the dominant factor giving rise to the observed stereocontrol.

Angewandte Chemie, International Edition published new progress about Acylation catalysts (stereoselective, kinetic resolution). 52010-22-7 belongs to class benzofurans, name is 4-Chlorophthalide, and the molecular formula is C8H5ClO2, Computed Properties of 52010-22-7.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem