28123-71-9

Upstream product

• 1192-62-7 1-(2-furyl)-1-ethanone 
• 100-01-6 4-nitro-aniline 
• 100-00-5 4-chlorobenzonitrile 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 586-78-7 para-nitrophenyl bromide 
• 100-05-0 4-nitrobenzenediazonium chloride 

Downstream Products

• 137503-52-7 (3-Chloro-2-methyl-phenyl)-{4-[5-(4-nitro-phenyl)-furan-2-yl]-thiazol-2-yl}-amine 
• 39170-35-9 2-bromo-1-(5-(4-nitrophenyl)furan-2-yl)ethanone 
• 42143-01-1 4-[5-(4-nitro-phenyl)-furan-2-yl]-thiazol-2-ylamine 
• 137503-53-8 (4-Chloro-2-methyl-phenyl)-{4-[5-(4-nitro-phenyl)-furan-2-yl]-thiazol-2-yl}-amine 
• 137503-49-2 (2-Chloro-phenyl)-{4-[5-(4-nitro-phenyl)-furan-2-yl]-thiazol-2-yl}-amine 
• 137503-48-1 (4-Chloro-phenyl)-{4-[5-(4-nitro-phenyl)-furan-2-yl]-thiazol-2-yl}-amine 
• 137503-54-9 (4-Bromo-phenyl)-{4-[5-(4-nitro-phenyl)-furan-2-yl]-thiazol-2-yl}-amine 
• 137503-50-5 {4-[5-(4-Nitro-phenyl)-furan-2-yl]-thiazol-2-yl}-o-tolyl-amine 
• 137503-51-6 {4-[5-(4-Nitro-phenyl)-furan-2-yl]-thiazol-2-yl}-p-tolyl-amine 
• 137503-55-0 {4-[5-(4-Nitro-phenyl)-furan-2-yl]-thiazol-2-yl}-pyridin-2-yl-amine 
• 137503-47-0 {4-[5-(4-Nitro-phenyl)-furan-2-yl]-thiazol-2-yl}-phenyl-amine 
• 1312997-70-8 2-hydroxy-2-(5-(4-nitrophenyl)furan-2-yl)ethyl acetate 
• 1312997-78-6 (R)-1-(5-(4-nitrophenyl)furan-2-yl)ethane-1,2-diyl diacetate 
• 1312997-74-2 (S)-2-hydroxy-2-(5-(4-nitrophenyl)furan-2-yl)ethyl acetate 

Relevant academic research and scientific papers

Synthesis of 4-(5-Nitrophenylfur-2-yl)-1,2,3-thia- and Selenadiazoles

Arylation of 2-acetylfuran with o-, m-, and p-nitrophenyldiazonium salts under the conditions of the Gomberg-Bachmann reaction has afforded the corresponding 5-(nitrophenyl)-2-acetylfurans. Their carbo-ethoxyhydrazones have undergone the cyclization into stable 4-(5-nitrophenylfur-2-yl)-1,2,3-thiadiazoles under the conditions of the Hurd-Mori reaction. Analogous semicarbazones have afforded the corresponding selenadiazoles upon oxidation with selenium dioxide. The analysis of electronic absorption spectra of the obtained hybrid heterocycles has shown that the conjugation of the phenyl and the furan ring in o-nitrophenyl derivatives is distorted due to steric hindrance, whereas the effect of direct polar conjugation leading to strong bathochromic shift of the absorption band has been observed in the case of the p-nitro derivatives. The position and intensity of the bands in the electronic absorption spectra of the studied compounds are determined by electronic as well as steric factors. The difference in the length of conjugation chain determined by the position of the nitro group in the phenyl fragment also contributes to the observed trend. The introduction of selenadiazole fragment instead of thiadiazole one has caused slight bathochromic shift of the band in the electron absorption spectra.

Polyaniline-Induced C-H Arylation of Arenes with Arenediazonium Salts

A reduced form of polyaniline has been shown to induce direct arylation of an arenediazonium salt with an arene (Gomberg-Bachmann reaction) to give the cross-coupling product in moderate to good yields under mild conditions. Various arenediazonium salts and arenes, including heteroarenes such as furans, thiophenes, and pyrroles, are employed for the reaction. The most favorable combination of substrates is an electron-poor arenediazonium salt with an electron-rich heteroarene. Investigation of the mechanism by reactions with radical scavengers and experiments on kinetic isotope effects indicated the occurrence of a radical chain reaction initiated by one-electron reduction of an arenediazonium salt by the polyaniline. Only 1 mol % (based on aniline tetramer) of the polyaniline is required for the cross-coupling reaction to occur. This reaction proceeds under metal-free conditions and with no need for photonic activation.

Efficient Pd-catalyzed direct arylations of heterocycles with unreactive and hindered aryl chlorides

A highly electron-rich Pd complex can efficiently catalyze the direct arylation of heteroaromatics with unreactive and sterically congested aryl chlorides.

Stereoselective bioreduction of 1-(5-phenylfuran-2-yl)-ethanones mediated by baker's yeast

Baker's yeast mediated reduction of various phenylfuran-2-yl-ethanones has been studied. The influence of the reaction conditions, the type and position of the substituents, as well the presence of various additives on the enantiomeric composition of the products and the reaction yield are discussed. The absolute configuration of the reaction products was established using a retrosynthetic procedure.

Substituent effects on the stereochemical outcome of the baker's yeast-mediated biotransformation of α-hydroxy- and α-acetoxymethyl-5-phenylfuran-2-yl-ethanones

In this Letter the baker's yeast-mediated biotransformation of variously substituted α-hydroxy- and α-acetoxymethyl-5-phenylfuran-2-yl-ethanones is described. The stereochemical outcome of the reactions was strongly influenced by the nature of the substituents on the phenyl ring.

Low catalyst loading ligand-free palladium-catalyzed direct arylation of furans: An economically and environmentally attractive access to 5-arylfurans

The direct 5-arylation of furans at very low catalyst loading using Pd(OAc)2 as catalyst without added ligand proceed in high yields. Turnover numbers up to 10000 have been obtained for the coupling of several activated aryl bromides. A wide ra

FURANTHIAZOLE DERIVATIVES AS HEPARANASE INHIBITORS

The invention provides a compound of formula (I) or a pharmaceutically acceptable salt or prodrug thereof: (I) wherein the groups Q, R2, R3, R4 and R5 represent various substituent groups, and their use as inhibitors of heparanase.