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New molecules with a triphenylmethane-type structure have been synthesised based on the structure of coloured compounds obtained from natural substrates.Satisfactory yields were obtained from benzofuran derivatives as starting material, which have been condensed in methanol with aromatic aldehydes in the presence of catalytic amounts of mineral acids.Several of the new compounds behave as pH indicators.The condensation products, obtained from suitably functionalized starting products, can be easily oxidised giving rise to new triphenylmethane-type dyes, such as 10.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1319O – PubChem

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This invention is to provide a compound of the formula: wherein R1 is an optionally substituted 5- to 6-membered ring; the ring A is an optionally substituted 6- to 7-membered ring; the ring B is an optionally substituted benzene ring; n is an integer of 1 or 2; Z is a chemical bond or a divalent group; R2 is (1) an optionally substituted amino group in which a nitrogen atom may form a quaternary ammonium, (2) an optionally substituted nitrogen-containing heterocyclic ring group which may contain a sulfur atom or an oxygen atom as ring constituting atoms and wherein a nitrogen atom may form a quaternary ammonium, (3) a group binding through a sulfur atom or (4) a group of the formula: ?wherein k is 0 or 1, and when k is 0, a phosphorus atom may form a phosphonium; and R5 and R6 are independently an optionally substituted hydrocarbon group, an optionally substituted hydroxy group or an optionally substituted amino group, and R5 and R6 may bind to each other to form a cyclic group together with the adjacent phosphorus atom, or a salt thereof , which is useful for antagonizing CCR5 and also for the prevention and treatment of infectious disease of HIV.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1318O – PubChem

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2,3-Dihydrobenzofurans are key pharmacophores in many natural and synthetic bioactive molecules. A biocatalytic strategy is reported here for the highly diastereo- and enantioselective construction of stereochemically rich 2,3-dihydrobenzofurans in high enantiopurity (>99.9% de and ee), high yields, and on a preparative scale via benzofuran cyclopropanation with engineered myoglobins. Computational and structure-reactivity studies provide insights into the mechanism of this reaction, enabling the elaboration of a stereochemical model that can rationalize the high stereoselectivity of the biocatalyst. This information was leveraged to implement a highly stereoselective route to a drug molecule and a tricyclic scaffold featuring five stereogenic centers via a single-enzyme transformation. This work expands the biocatalytic toolbox for asymmetric C?C bond transformations and should prove useful for further development of metalloprotein catalysts for abiotic carbene transfer reactions.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1330O – PubChem

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2-(5-Resorcinyl)benzofurans have been synthesised by the palladium catalysed cross coupling of 2-trimethylstannyl- or 2-bromozinc benzofurans with the appropriately functionalised 5-iodoresorcinols.These were synthesised by the tri-isopropylsilyloxy directed remote (C-5) lithiation/iodination of the O,O-di(triisopropylsilyl)resorcinoltricarbonylchromium(0) complex.The method was applied to the synthesis of moracin M, a phytoalexin of Morus alba Linn.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1323O – PubChem

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An efficient and environmentally benign heterogeneous catalytic process for the synthesis of 2,3-unsubstituted benzo[b]furans has been established via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals. By utilizing tin-exchanged H-beta zeolite (Sn-beta) as catalyst, a wide range of functionalized 2,3-unsubstituted benzo[b]furans could be prepared in good to excellent yields. The Sn-beta zeolite catalyst also exhibited excellent shape selectivity on the cyclization of meta-substituted 2-aryloxyacetaldehyde acetals, and 6-substituted isomers were preferably formed up to 97% regio-selectivity. Moreover, Sn-beta zeolite could be easily recovered and reused without any noticeable activity loss.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1327O – PubChem

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An optimized process for the preparation of 6-hydroxybenzofuran is described. This process consists of three steps: the reaction of 2-hydroxy-4-methoxybenzaldehyde with chloroacetic acid, the formation of the 6-methoxybenzofuran in acetic anhydride, and the demethylation with sodium 1-dodecanethiolate to afford the desired product. The entire process is safe, cost effective, environmentally benign, and scalable. A production scale of over 2.6 kg product was achieved in good overall yield.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1326O – PubChem

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The reaction of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) with 6-methoxy-3-methylbenzofuran gave carbon-oxygen adduct.The reaction in less polar solvents such as benzene and CH2Cl2 proceeds faster than that in more polar solvents such as THF and dioxane.In contrast, the reaction of DDQ with indoles gave carbon-carbon adducts.This reaction proceeds rapidly with increasing solvent polarity.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1328O – PubChem

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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 isobutyl complexes and their carboxylation products were isolated and structurally characterized by X-ray crystallographic analyses, thus offering important information on the reaction mechanism.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1329O – PubChem

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In the present work we report the synthesis of four new ER ligands which can be used as scaffolds for the introduction of the basic side chains necessary for antiestrogenic activity. Affinities and agonist/antagonist characterization of the ligands for both ERalpha and ERbeta have been determined in a competitive radioligand assay, and in an in vitro coactivator recruitment functional assay, respectively. Molecular modelling techniques have been used in order to rationalize the experimental results. Compound 2 is reported as a novel ERbeta-agonist/ERalpha-antagonist. Two compounds show an interesting antitumour profile towards two pancreatic cancer cell lines and have been selected for in vivo assays.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1324O – PubChem

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Copper-mediated alkylation of furan and thiophene derivatives with cyclic ethers

An efficient and complementary copper-catalyzed alkylation of (benzo)furans/(benzo)thiophenes with cyclic ethers was reported. A broad range of C2 heteroaryl-substituted cyclic ethers were obtained in moderate to good yields. The results of control experiments indicated that this transformation might proceed via a radical process.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H1331O – PubChem