588-96-5Relevant articles and documents
Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions
Yang, Yu-Ming,Yan, Wei,Hu, Han-Wei,Luo, Yimin,Tang, Zhen-Yu,Luo, Zhuangzhu
, p. 12344 - 12353 (2021/09/02)
A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.
Synthesis, evaluation and in silico studies of novel BRD4 bromodomain inhibitors bearing a benzo[d]isoxazol scaffold
Zhang, Maofeng,Liu, Zhuyun,Wang, Lizhong,Li, Yan,Ma, Yonggang
, (2021/02/12)
Abstract: The BRD4 protein is associated with various diseases, which has been an attractive target for the treatment of cancer and inflammation. This paper is a follow-up to our previous studies, in which we report the structure-based design, synthesis, and evaluation of a new class of small-molecule BRD4 bromodomain inhibitors bearing a benzo[d]isoxazol scaffold. The SARs focused on exploration of the 2′ or 3′ position to afford novel inhibitors that may avoid potential metabolically unstable site. The most potent inhibitor 13f exhibited high binding affinity to BRD4(1) with a ΔTm value of 7.8 °C as evaluated in thermal shift assay (TSA). The potent activity was also demonstrated by a peptide competition assay with an IC50 value of 0.21?μM. The docking studies revealed the binding mode of the compounds with the active site of BRD4(1). In addition, in silico predictions indicated that these compounds possessed good drug-likeness and pharmacokinetic profile. Graphic abstract: This paper is a follow-up to our previous studies, in which we report the structure-based design,synthesis, and evaluation of a new class of small-molecule BRD4 bromodomain inhibitors bearing a benzo[d]isoxazolscaffold.[Figure not available: see fulltext.].
9,9′-bifluorenylidene derivatives as novel hole-transporting materials for potential photovoltaic applications
Kula, Slawomir,Paj?k, Agnieszka,Szlapa-Kula, Agata,Mieszczanin, Angelika,Gnida, Pawe?,Lipiński, Marek,Schab-Balcerzak, Ewa
, (2019/11/26)
Novel 9,9′-bifluorenylidene derivatives were designed to study the effect of alkyl chain length on selected physical properties. The structure of the synthesized compounds was confirmed by using NMR spectroscopy (1H, 13C, H–H COSY, H–C HMQC, H–C HMBC) and elemental analysis. They showed high thermal stability and undergo decomposition in the range of 388–400 °C. As was revealed by DSC investigations, they can be converted from crystalline to amorphous materials with relatively high glass transition temperature. The replacement of the alkyl chains from ethyl to butyl resulted in a significant negative impact on melting and glass transition temperatures. The synthesized derivatives undergo reversible electrochemical oxidation and reduction and showed a very low energy band gap (1.47 and 1.79 eV). They intensively absorb the light up 550 nm and also exhibited a week absorption band in the range of 550–750 nm. Their hole transporting ability was tested in perovskite solar cells. Additionally, the effect of the doping concentration of Li+ on photovoltaic device performance for these compounds was investigated. It should be stressed found that 9,9′-bifluorenylidene derivative substituted with ethyl units applied as hole transporting materials in perovskite solar cells demonstrated the highest device efficiency of 7.33% higher than of the spiro-OMeTAD utilized for preparation of the reference cell (4.40%).
Preparation method of p-bromophenylalkyl ether
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Paragraph 0044-0058, (2020/07/15)
The invention relates to a preparation method of p-bromophenylalkyl ether, wherein the preparation method comprises the steps: carrying out bromination reaction on phenylalkyl ether, hydrobromic acidand an oxidant in an organic solvent to prepare p-bromophenylalkyl ether. A chlorinated non-polar solvent is used as a reaction solvent, so that the para-position substitution selectivity of the bromination reaction is greatly improved, the yield of the bromination reaction is remarkably improved, p-bromophenylalkyl ether is prepared by replacing an etherification reaction route with the bromination reaction, toxic diethyl sulfate does not need to be used in the preparation process, and potential safety hazards are avoided; meanwhile, the dosage of the solvent is greatly reduced, the loading capacity of the raw materials of a reaction kettle is greatly improved, the production efficiency is greatly improved, and the production time is shortened; the post-treatment is simple, the reaction solvent can be recycled, and the comprehensive production cost is reduced; the method has the advantages of easily available raw materials, simple operation, low risk, high yield, high product purity,small pollution of the whole process, and suitableness for large-scale industrial production.
Method for catalyzing deaminized boric acid esterification or halogenation of arylamine
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Paragraph 0063; 0094-0096, (2020/01/12)
The invention belongs to the technical field of organic synthesis and in particular discloses a method for catalyzing deaminized boric acid esterification or halogenation of arylamine. The method comprises the following steps: putting arylamine and a nitroso type compound into a mixed solvent, and performing a reaction at 0-5 DEG; and further adding a raw material capable of providing a functionalization group A and a catalysis amount of a reaction accelerator, and performing deamination functionalization reaction under light radiation at 10-50 DEG C, so as to obtain a product that an amino site of the arylamine is modified by the functionalization group A. Due to synergetic control on substrates, reaction solvents, material mixing modes, temperatures, reaction accelerators and addition amounts, boric acid esterification or halogenation of arylamine, particularly electron donating substituted arylamine which is hard to treat effectively in technical schemes of the industry, can be achieved.
Microwave-assisted synthesis method for ethylation reaction
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Paragraph 0012, (2019/10/05)
The invention relates to a microwave-assisted synthesis method for an ethylation reaction. The method is characterized in that a reaction substrate is in an organic solvent, trifluoroacetic acid ethyl ester is taken as an ethylation reagent, in the presence of an alkali, microwave-assisted heating is carried out for 2 minutes, and a corresponding ethylation product can be obtained. The invention provides a new method for the ethylation reaction. The reaction rate of the method is several times higher than that of a traditional method, the operation is simple and convenient, the cost is low, the reaction time is short, the application range of the substrate is wide, the use of the expensive or hypertoxic ethylation reagent can also be avoided, and the method has higher application value.
Selective Halogenation Using an Aniline Catalyst
Samanta, Ramesh C.,Yamamoto, Hisashi
supporting information, p. 11976 - 11979 (2015/08/18)
Electrophilic halogenation is used to produce a wide variety of halogenated compounds. Previously reported methods have been developed mainly using a reagent-based approach. Unfortunately, a suitable "catalytic" process for halogen transfer reactions has yet to be achieved. In this study, arylamines have been found to generate an N-halo arylamine intermediate, which acts as a highly reactive but selective catalytic electrophilic halogen source. A wide variety of heteroaromatic and aromatic compounds are halogenated using commercially available N-halosuccinimides, for example, NCS, NBS, and NIS, with good to excellent yields and with very high selectivity. In the case of unactivated double bonds, allylic chlorides are obtained under chlorination conditions, whereas bromocyclization occurs for polyolefin. The reactivity of the catalyst can be tuned by varying the electronic properties of the arene moiety of catalyst.
An eco-friendly asymmetric organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes: Application on the synthesis of chiral indoles
Feu, Karla Santos,Deobald, Anna Maria,Narayanaperumal, Senthil,Correa, Arlene G.,Weber Paixao, Marcio
supporting information, p. 5917 - 5922 (2013/09/23)
The asymmetric Michael addition of malonates to α,β-unsaturated aldehydes using a modified Jorgensen-Hayashi organocatalyst in EtOH:brine solvent media is reported. The procedure proceeds smoothly to afford the corresponding Michael adducts in good yields with excellent enantioselectivities. The resulting Michael adducts represent excellent building blocks for the synthesis of chiral indoles. The asymmetric Michael reaction using a modified Jorgensen-Hayashi organocatalyst in EtOH:brine solvent media is reported. This procedure afforded the corresponding Michael adducts in good yields and with excellent enantioselectivities. The resulting adducts were further used as chiral building blocks for the synthesis of indoles. Copyright
SNAAP sulfonimidate alkylating agent for acids, alcohols, and phenols 1
Maricich, Tom J.,Allan, Matthew J.,Kislin, Brett S.,Chen, Andrea I-T.,Meng, Fan-Chun,Bradford, Christine,Kuan, Nai-Chia,Wood, Jeremy,Aisagbonhi, Omonigho,Poste, Alethea,Wride, Dustin,Kim, Sylvia,Santos, Therese,Fimbres, Michael,Choi, Dianne,Elia, Haydi,Kaladjian, Joseph,Abou-Zahr, Ali,Mejia, Arturo
, p. 3361 - 3368 (2014/01/06)
Stable, crystalline ethyl N-tert-butyl-4-nitrobenzenesulfonimidate has been prepared in high yield by direct O-ethylation of N-tert-butyl-4- nitrobenzenesulfonamide with iodoethane and silver(I) oxide in dichloromethane. This sulfonimidate directly ethylates various acids to esters; the stronger the acid, the faster it alkylates and in higher yield. It readily ethylates alcohols and phenols to ethers at room temperature in the presence of tetrafluoroboric acid catalyst without molecular rearrangements or racemization. We have defined these reactions as SNAAP alkylations: [substitution, nucleophilic of acids, alcohols and phenols]. The hard sulfonimidate alkylating agent is chemoselective, preferring oxygen > nitrogen > sulfur. The sulfonamide byproduct of alkylation is readily recycled to the sulfonimidate. Georg Thieme Verlag Stuttgart . New York.
In situ acidic carbon dioxide/water system for selective oxybromination of electron-rich aromatics catalyzed by copper bromide
Liu, An-Hua,Ma, Ran,Zhang, Meng,He, Liang-Nian
, p. 38 - 43 (2013/01/15)
Carbon dioxide, being one of the major greenhouse gases responsible for global warming, its atmospheric level grows ever faster since the beginning of industrial era. Great efforts have been devoted to developing versatile technologies/processes to adjust and manipulate the rapid growth of CO 2 emission. Besides CO2 capture and storage/sequestration (CCS) to control its emission, chemical utilization of the captured CO 2 (CCU) emerges to be a rational technique for economical benefits as well as environmental concerns. As for the aim of CO2 utilization, an environmentally benign CO2/water reversible acidic system was developed for the copper (II)-catalyzed selective oxybromination of electron-rich aromatics without the need of any conventional acid additive and organic solvent. Notably, up to 95% yields of the bromination products were attained with good regio-selectivity when cupric bromide was used as the catalyst and lithium bromide as a cheap and easy handling bromine source under supercritical CO2. The catalytic system worked well for electron-rich aromatics including ethers, sulfides and mesitylene. Carbonic acid in situ formed from CO2 and water is supposed to act as the proton donator in the Bronsted acid-promoted reaction. Notably, CO2 in this study serves as a reaction medium and a promoter in conjunction with water and also provides safe environment for aerobic reactions. Given with excellent reaction efficiency as well as no need of neutralization disposal, this process thus represents an environmentally friendly approach for aerobic bromination of aromatics with essential reduction of CO2 emission as well as an economically beneficial way for application of captured CO2.
