856771-93-2

Upstream product

• 22367-83-5 ethyl 3-phenyl-1-benzofuran-2-carboxylate 
• 1060728-90-6 2-methylene-3-phenyl-2,3-dihydro-1-benzofuran-3-ol 
• 55038-01-2 benzofuran-2-yl-methanol 
• 108-86-1 bromobenzene 
• 4846-21-3 O-phenylhydroxylamine 
• 5661-50-7 N-(phenoxy)acetamide 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 98-80-6 phenylboronic acid 
• 64908-64-1 2-phenoxyisoindol-1,3-dione 
• 1005328-49-3 2-(1-hydroxy-1-phenylprop-2-ynyl)phenol 

Downstream Products

• 890715-13-6 2-[(3-phenyl-1-benzofurane-2-yl)methyl]-1H-isoindole-1,3(2H)-dione 
• 1393181-05-9 9-((3-phenylbenzofuran-2-yl)methyl)-9H-purin-6-amine 
• 1393176-53-8 (3-phenylbenzofuran-2-yl)methyl methanesulfonate 

Relevant academic research and scientific papers

A recyclable palladium-catalyzed synthesis of 2-methylene-2,3- dihydrobenzofuran-3-ols by cycloisomerization of 2-(1-hydroxyprop-2-ynyl)phenols in ionic liquids

A recyclable palladium-catalyzed synthesis of 2-methylene-2,3- dihydrobenzofuran-3-ols 2 by heterocyclization of 2-(1-hydroxyprop-2-ynyl) phenols 1 in an ionic liquid medium (BmimBF4) is presented. The process takes place under relativelyn mild conditions (100 °C, 5 h) in the presence of catalytic amounts (2 mol %) of PdI2 in conjunction with KI (5 equiv with respect to PdI2) and an organic base, such as morpholine (1 equiv with respect to 1), to give 2 in high yields (70%-86%). The PdI 2-KI catalytic system could be recycled up to six times without appreciable loss of activity. Moreover, products 2 could be easily converted in a one-pot fashion into 2-hydroxymethylbenzofurans 3 (52%-71%, based on 1) and 2-methoxymethylbenzofurans 4 (52%-80%, based on 1) by acid-catalyzed allylic isomerization or allylic nucleophilic substitution.

Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity

Give it a tweak: A novel oxidizing directing group was developed for a rhodium(III)-catalyzed C-H functionalization of N-phenoxyacetamides with alkynes. A small change in the reaction conditions leads to either ortho-hydroxyphenyl-substituted enamides or cyclization to deliver benzofurans with high selectivity (see scheme; Cp=C5Me5). Copyright

Palladium-catalyzed direct arylation of polysubstituted benzofurans

An efficient access to 2-substituted 3-arylbenzofurans through a palladium-catalyzed C3 direct arylation of 2-substituted benzofurans with aryl bromides is described. The scope and limitation of this reaction was studied. The method tolerates a variety of functional groups on the aryl halide and has been successfully extended to polysubstituted benzofurans to obtain the corresponding 3-arylbenzofurans with good to excellent yields.

A novel synthesis of 2-functionalized benzofurans by palladium-catalyzed cycloisomerization of 2-(1-hydroxyprop-2-ynyl)phenols followed by acid-catalyzed allylic isomerization or allylic nucleophilic substitution

(Chemical Equation Presented) A novel two-step synthesis of 2-hydroxymethylbenzofurans 3 and 2-alkoxymethylbenzofurans 4-6, based on palladium-catalyzed cycloisomerization of 2-(1-hydroxyprop-2-ynyl)phenols 1 under basic conditions to give 2-methylene-2,3-dihydrobenzofuran-3-ols 2, followed by acid-catalyzed isomerization or allylic nucleophilic substitution with alcohols as nucleophiles, is reported. Cycloisomerization reactions leading to 2 (80-98% yields) were carried out at 40°C in MeOH as the solvent, in the presence of a base and catalytic amounts of PdX2 + 2KX (X = Cl, I). Isomerization reactions of 2 readily occurred at 25-60 °C in DME as the solvent, with H2SO4 as the proton source, to give 2-hydroxymethylbenzofurans 3 in 65-90% yields. In a similar manner, allylic nucleophilic substitution reactions of 2 with ROH as nucleophiles [carried out at 25-40°C in ROH (R = Me) or ROH-DME mixtures (R = Bu, Bn) in the presence of H2SO4] afforded 2-alkoxymethylbenzofurans 4, 5, and 6 (R = Me, Bu, and Bn, respectively), in 65-98% yields.

CARBOXAMIDE DERIVATIVE

An SGLT inhibitor comprising a compound of the formula: (|) wherein the ring A is an optionally substituted ring; R1 is an optionally substituted hydrocarbon group, etc.; each of R2 and R3 independently is a hydrogen atom, an optionally substituted hydrocarbon group, etc.; R4 is an optionally substituted hydrocarbon group, etc.; and X is a bivalent chain group whose main chain consists of 1 to 6 atoms. This SGLT inhibitor is useful as a preventive/therapeutic agent for diabetes mellitus, obesity, hypertension, hyperlipemia, etc.