95-55-6Relevant articles and documents
Continuous synthesis of aminophenols from nitroaromatic compounds by combination of metal and biocatalyst
Luckarift, Heather R.,Nadeau, Lloyd J.,Spain, Jim C.
, p. 383 - 384 (2005)
The combined action of immobilized hydroxylaminobenzene mutase and zinc in a flow-through system catalyzes the conversion of nitroaromatic compounds to the corresponding ortho-aminophenols, including a novel analog of chloramphenicol.
Modification of poly (ethylene glycol) with a multifunctional silane ligand, stabilization of Ag nanoparticles and its catalytic activity toward nitro-aromatics reduction
Fathalipour, Soghra,Zolali, Amin,Najafpour, Behzad,Pourbeyram, Sima,Zirak, Maryam
, p. 47 - 54 (2021)
The modification of poly (ethylene glycol) (PEG) with (3, 3′-bis-(3-triethoxysilylpropyl)-2, 2′-dithioxo [5, 5′] bithiazolidinylidene-4, 4′-dione) ligand was performed in the presence of Et3N in toluene (MPEG). With the addition of AgNO3, MPEG with obtain
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Brown,Warner
, (1923)
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Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes
Fu, Lihua,Li, Dingzhong,Lu, Hao,Qiu, Renhua,Sun, Tulai,Xing, Chen,Yang, Tianbao
, (2022/01/11)
The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).
Retro-aza-Michael reaction of an o-aminophenol adduct in protic solvents inspired by natural products
Kakeya, Hideaki,Kaneko, Kensuke,Nishimura, Shinichi,Takahashi, Nobuaki,Takenaka, Kei
, (2021/02/26)
α,β-Unsaturated carbonyls are reactive group often found in bioactive small molecules. Their non-specific reaction with biomolecules can be the cause of the low efficacy and unexpected side-effects of the molecule. Accordingly, unprotected α,β-unsaturated carbonyls are not often found in drugs. Here, we report that o-aminophenol is a new masking group of α,β-unsaturated ketone, which is inspired by natural products saccharothriolides. o-Aminophenol adduct of α,β-unsaturated ketone, but not those of α,β-unsaturated amide or ester, undergoes a retro-Michael reaction to yield o-aminophenol and the Michael acceptor. This reaction was observed only in protic solvents, such as MeOH and aqueous MeOH. In contrast, o-anisidine was not eliminated from its Michael adduct. o-Aminophenol may be a promising masking tool of highly-reactive bioactive α,β-unsaturated carbonyl compounds.