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.
Ruthenium(II)-Catalyzed Positional Selective C-H Oxygenation of N-Aryl-2-pyrimidines
Sarkar, Tanumay,Pradhan, Sourav,Punniyamurthy, Tharmalingam
, p. 6444 - 6453 (2018)
Efficient Ru-catalyzed regioselective C-H oxygenation of N-aryl-2-pyrimidines is described with aryl carboxylic acids in the presence of AgSbF6 as an additive and Ag2CO3 as an oxidant. The reaction can be extended to alkyl
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
Synthesis and characterization of Pd nanoparticle-modified magnetic Sm2O3–ZrO2 as effective multifunctional catalyst for reduction of 2-nitrophenol and degradation of organic dyes
Yilmaz, Erkan,Tut, Y?ld?z,Turkoglu, Orhan,Soylak, Mustafa
, p. 1721 - 1731 (2018)
In this study, Pd nanoparticle-modified magnetic Sm2O3–ZrO2 material (Pd–Fe3O4–Sm2O3–ZrO2) as multifunctional catalyst was fabricated and used for catalytic reduction
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).
A DFT and experimental study of the spectroscopic and hydrolytic degradation behaviour of some benzylideneanilines
Nelson, Peter N.,Robertson, Tahjna I.
, (2021/10/12)
The spectroscopic and hydrolytic degradation behaviour of some N-benzylideneanilines are investigated experimentally and theoretically via high quality density function theoretical (DFT) modelling techniques. Their absorption and vibrational spectra, accurately predicted by DFT calculations, are highly dependent on the nature of the substituents on the aromatic rings, hence, though some of their spectroscopic features are similar, energetic differences exist due to differences in their electronic structures. Whereas the o-hydroxy aniline derived adducts undergo hydrolysis via two pathways, the most energetically economical of which is initiated by a fast enthalpy driven hydration, over a conservative free energy (ΔG?) barrier of 53 kJ mol?1, prior to the rate limiting entropy controlled lysis step which occurs via a conservative barrier of ca.132 kJ mol?1, all other compounds hydrolyse via a slower two-step pathway, limited by the hydration step. Barriers heights for both pathways are controlled primarily by the structure and hence, stability of the transition states, all of which are cyclic for both pathways.
Single-Cell-Based Screening and Engineering of d -Amino Acid Amidohydrolases Using Artificial Amidophenol Substrates and Microbial Biosensors
An, Jung-Ung,Kim, Haseong,Kwon, Kil Koang,Lee, Dae-Hee,Lee, Hyewon,Lee, Jin-Young,Lee, Seung-Goo,Park, Sung Hyun,Rha, Eugene,Yeom, Soo-Jin
, p. 1203 - 1211 (2022/01/27)
Enantiomerically pure d-amino acids are important intermediates as chiral building blocks for peptidomimetics and semisynthetic antibiotics. Here, a transcriptional factor-based screening strategy was used for the rapid screening of d-stereospecific amino acid amidase via an enzyme-specific amidophenol substrate. We used a d-threonine amidophenyl derivative to produce 2-aminophenol that serves as a putative enzyme indicator in the presence of d-threonine amidases. Comparative analyses of known bacterial species indicated that several Bacillus strains produce amidase and form putative indicators in culture media. The estimated amidase was cloned and subjected to rapid directed evolution through biosensor cells. Consequently, we characterized the F119A mutation that significantly improved the catalytic activity toward d-alanine, d-threonine, and d-glutamate. Its beneficial effects were confirmed by higher conversions and recurrent applications of the mutant enzyme, compared to the wild-type. This study showed that rapid directed evolution with biosensors coupled to designed substrates is useful to develop biocatalytic processes.
Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines
Gillespie, James E.,Morrill, Charlotte,Phipps, Robert J.
supporting information, p. 9355 - 9360 (2021/07/19)
The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.
Method for catalytically synthesizing ortho-aminophenol
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Paragraph 0025-0044, (2021/07/08)
The invention provides a method for catalytically synthesizing ortho-aminophenol. The method comprises the following steps: taking sodium o-nitrophenolate as a reaction substrate and rhodium carbonyl chloride of superparamagnetic nanoparticle loaded ionic liquid as a catalyst, adding a solvent, introducing hydrogen, and carrying out reduction reaction for 1-10 hours under the conditions that the temperature is 50-80 DEG C and the pressure is 0.3-1.0 Mpa; after the reaction is finished, applying an external magnetic field to attract the catalyst, and then carrying out acidification, filtration, washing and vacuum drying on the reaction liquid to obtain ortho-aminophenol; and after the reaction is finished, simply recovering the catalyst through an external magnetic field. The recovered catalyst can be repeatedly used, and the activity is not obviously reduced. Compared with the traditional process, the method provided by the invention has the advantages of low reaction temperature, simple operation of a catalytic system, high yield, good reusability and good industrial prospect.
Electrochemical-induced hydroxylation of aryl halides in the presence of Et3N in water
Ke, Fang,Lin, Chen,Lin, Mei,Long, Hua,Wu, Mei,Yang, Li,Zhuang, Qinglong
supporting information, p. 6417 - 6421 (2021/08/03)
A thorough study of mild and environmentally friendly electrochemical-induced hydroxylation of aryl halides without a catalyst is presented. The best protocol consists of hydroxylation of different aryl iodides and aryl bromides by water solution in the presence of Et3N under air, affording the target phenols in good isolated yields. Moreover, aryl chlorides were successfully employed as substrates. This methodology also provides a direct pathway for the formation of deoxyphomalone, which displayed a significant anti-proliferation effect.
