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88-74-4Relevant articles and documents
Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines
Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju
supporting information, p. 1915 - 1923 (2021/02/06)
Candida parapsilosisATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method can selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which are useful for the preparation of pharmaceuticals, polymers and agrochemicals were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (≥10 cycles) and is a robust free flowing powder, stored and used after eight months without any loss in catalytic activity.
Discovery and development of 2-aminobenzimidazoles as potent antimalarials
Avery, Vicky M.,Challis, Matthew P.,Creek, Darren J.,De Paoli, Amanda,Devine, Shane M.,Kigotho, Jomo K.,MacRaild, Christopher A.,Norton, Raymond S.,Scammells, Peter J.,Siddiqui, Ghizal
, (2021/06/03)
The emergence of Plasmodium falciparum resistance to frontline antimalarials, including artemisinin combination therapies, highlights the need for new molecules that act via novel mechanisms of action. Herein, we report the design, synthesis and antimalarial activity of a series of 2-aminobenzimidazoles, featuring a phenol moiety that is crucial to the pharmacophore. Two potent molecules exhibited IC50 values against P. falciparum 3D7 strain of 42 ± 4 (3c) and 43 ± 2 nM (3g), and high potency against strains resistant to chloroquine (Dd2), artemisinin (Cam3.IIC580Y) and PfATP4 inhibitors (SJ557733), while demonstrating no cytotoxicity against human cells (HEK293, IC50 > 50 μM). The most potent molecule, possessing a 4,5-dimethyl substituted phenol (3r) displayed an IC50 value of 6.4 ± 0.5 nM against P. falciparum 3D7, representing a 12-fold increase in activity from the parent molecule. The 2-aminobenzimidazoles containing a N1-substituted phenol represent a new class of molecules that have high potency in vitro against P. falciparum malaria and low cytotoxicity. They possessed attractive pharmaceutical properties, including low molecular weight, high ligand efficiency, high solubility, synthetic tractability and low in vitro clearance in human liver microsomes.
Magnetically‐recoverable Schiff base complex of Pd(II) immobilized on Fe3O4@SiO2 nanoparticles: an efficient catalyst for the reduction of aromatic nitro compounds to aniline derivatives
Azadi, Sedigheh,Esmaeilpour, Mohsen,Sardarian, Ali Reza
, p. 809 - 821 (2021/07/20)
Fe3O4@SiO2/Schiff base/Pd(II) is reported as a magnetically recoverable heterogeneous catalyst for the chemoselective reduction of aromatic nitro compounds to the corresponding amines through catalytic transfer hydrogenation (CTH). In this regard, a small amount of the nanocatalyst (0.52?mol% Pd) and hydrazine hydrate, showing safe characteristics and perfect ability as the hydrogen donor, were added to the nitro substrates. The experiments described the successful reduction of aromatic nitro compounds with good to excellent yields and short reaction times. The catalyst, due to its magnetic property, could be simply separated from the reaction mixture by a permanent magnet and reused in seven consecutive reactions without considerable loss in its activity. Moreover, the leaching of Pd was only 3.6% after the seventh run. Thus, the most striking feature of this method is to use a small amount of the magnetic nanocatalyst along with a cheap and safe hydrogen source to produce the important amine substances selectively, which makes the method economical, cheap, environmentally friendly, and simple. Graphic abstract: [Figure not available: see fulltext.]
A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride
Kalola, Anirudhdha G.,Prasad, Pratibha,Mokariya, Jaydeep A.,Patel, Manish P.
supporting information, p. 3565 - 3589 (2021/10/12)
The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.
Copper catalyzed reduction of azides with diboron under mild conditions
Chen, Yang,Deng, Shengqi,Gao, Yihua,Liu, Liwen,Liu, Yu,Lu, Da,Wang, Qianwen,Zhang, Xiao
supporting information, (2020/02/27)
We report herein the first Cu catalyzed reduction of azides with B2pin2 (pin = pinacolato) as the reductant under very mild conditions. A series of primary amines and amides were obtained in moderate to excellent yields with high chemoselectivity and good functional group tolerance. This reaction can be performed with a cheap copper salt, a simple NHC ligand and a diboron reagent.
CuIBiOI is an efficient novel catalyst in Ullmann-type CN– couplings with wide scope—A rare non-photocatalyic application
Djerdj, Igor,Kónya, Zoltán,Kocsis, Marianna,Kukovecz, ákos,Pálinkó, István,Sipos, Pál,Varga, Gábor
, (2020/07/02)
Preparation of a new, mixed-cationic layered CuIBiOI was prepared and its non-photocatalytic catalytic properties were explored. This solid substance had BiOI-like, lamellar and deflected structure resulting from CuI ion incorporation in the Bi2O2 layers. The as-prepared substance was fully characterized by XRD, Raman, far IR, UV–DR, XP spectroscopies, thermal (TG-DTG) and analytical (ICP-MS, SEM-EDX) methods, electron microscopies (SEM, TEM) as well as BET surface area measurements. By performing Ullmann-type CN– coupling reactions between aryl halides and aqueous ammonia, its catalytic capabilities were tested. The effects of solvents, added base and catalyst loading as well as reaction time and reaction temperature were scrutinized, and a green way for the reaction was identified. The recyclability of the catalyst without the loss of activity and its general applicability for a wide range of aryl halides were also demonstrated.
Preparation method of 2-nitro-aniline
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Paragraph 0014-0068, (2020/11/12)
The invention discloses a preparation method of 2-nitro-aniline. The method comprises the steps: under conditions of a high-boiling-point high-polarity solvent used as a reaction solvent and the presence of an inorganic acid, controlling the temperature to be 100 to 140 DEG C and carrying out normal-pressure desulfonation reaction on the 2-nitro-4-sulfonic aniline; and after the reaction is finished, carrying out vacuum concentration to remove the high-boiling-point high-polarity solvent, adding water, uniformly mixing, regulating the pH value to 8-10, sequentially extracting, washing, concentrating and drying to obtain the 2-nitro-aniline, and recycling the high-boiling-point high-polarity solvent after the reaction for reuse. According to the preparation method, a normal-pressure desulfonation reaction is carried out within a relatively low temperature range, the energy consumption in the preparation process is low, meanwhile, less waste salt is generated, only 2.7-3.3 tons of sodiumsulfate is generated according to 2-nitro-aniline per ton, the purity (HPLC) of the finally obtained 2-nitro-aniline product is greater than 97%, and the highest yield can reach 91%.
Divergent Late-Stage (Hetero)aryl C?H Amination by the Pyridinium Radical Cation
Ham, Won Seok,Hillenbrand, Julius,Jacq, Jér?me,Genicot, Christophe,Ritter, Tobias
supporting information, p. 532 - 536 (2019/01/04)
(Hetero)arylamines constitute some of the most prevalent functional molecules, especially as pharmaceuticals. However, structurally complex aromatics currently cannot be converted into arylamines, so instead, each product isomer must be assembled through a multistep synthesis from simpler building blocks. Herein, we describe a late-stage aryl C?H amination reaction for the synthesis of complex primary arylamines that other reactions cannot access directly. We show and rationalize through a mechanistic analysis the reasons for the wide substrate scope and the constitutional diversity of the reaction, which gives access to molecules that would not have been readily available otherwise.
Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides
Gupta, Sampa,Ansari, Alisha,Sashidhara, Koneni V.
supporting information, (2019/09/07)
A useful and efficient approach for the synthesis of nitroarenes from several aromatic amines (including heterocycles) using peroxide and base has been developed. This oxidative reaction is very easy to handle and afforded the products in good yields. Formation of benzamides from benzylamine was also successfully carried out with this metal-free catalytic system in good to excellent yields.
Preparing method of ultraviolet absorber UV-234
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Paragraph 0028; 0030; 0035; 0037; 0042; 0044, (2019/08/26)
The invention provides a preparing method of an ultraviolet absorber UV-234. The preparing method comprises the steps of conducting ammoniation, diazotization, coupling, first-step reduction, second-step reduction reaction and post-treatment on ortho-nitrochlorobenzene to prepare 2-[2'-hydroxy-3',5'-di(alpha,alpha-dimethyl benzyl)phenyl]benzotriazole. According to the preparing method, ortho-nitrochlorobenzene is ammonified by adopting ammonium hydroxide with the concentration of 10-25%, then is subjected to diazotization with nitrite to produce diazonium salt, no diazotization needs to occurunder a strong acid medium, by-product ammonium hydroxide of existing products of a company is comprehensively utilized, low emission of three wastes is achieved, and the required cost is low; a two-step reduction method is adopted in a reduction ring closing process of intermediate azo products, the situation is avoided that a strong reduction agent directly reduces azo double bonds into amine, impurity production is reduced, and not only is the purity of the products increased but also the product yield is increased.