10272-07-8Relevant academic research and scientific papers
Self-propagated Lossen rearrangement induced by a catalytic amount of activating agents under mild conditions
Hoshino, Yujiro,Shimbo, Yuki,Ohtsuka, Naoya,Honda, Kiyoshi
, p. 710 - 712 (2015)
A mild self-propagated Lossen rearrangement induced by a catalytic amount of activating agents in medium to high polar organic solvents has been developed. The rearrangement of aromatic and aliphatic hydroxamic acids in the presence of a catalytic amount (0.01 equiv) of acetic anhydride and an equimolar amount of base such as well-dried potassium carbonate afforded the corresponding amines in high yields. This alternative to traditional Lossen rearrangement provides a simple and mild method for the synthesis of amines from free hydroxamic acids.
Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation
Wang, Erfei,Chen, Kaixuan,Chen, Yinan,Zhang, Jiawei,Lin, Xinrong,Chen, Mao
, p. 17 - 21 (2020/11/04)
A porous polymeric ligand (PPL) has been synthesized and complexed with copper to generate a heterogeneous catalyst (Cu@PPL) that has facilitated the efficient C-N coupling with various (hetero)aryl chlorides under mild conditions of visible-light irradiation at 80 °C (58 examples, up to 99% yields). This method could be applied to both aqueous ammonia and substituted amines, and is compatible to a variety of functional groups and heterocycles, as well as allows tandem C-N couplings with conjunctive dihalides. Furthermore, the heterogeneous characteristic of Cu@PPL has enabled a straightforward catalyst separation in multiple times of recycling with negligible catalytic efficiency loss by simple filtration, affording reaction mixtures containing less than 1 ppm of Cu residue. [Figure not available: see fulltext.]
A new ligand for copper-catalyzed amination of aryl halides to primary(hetero)aryl amines
Chen, Dong,Dong, Xinrui,Jiang, Shang,Jiang, Sheng,Qiu, Yatao,Wu, Xiaoxing
supporting information, (2020/02/11)
N,N′-Bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide was found as a new ligand for copper-catalyzed amination of aryl iodides, bromides and chlorides to afford various primary (hetero)aryl amines. These reactions proceeded efficiently under mild conditions when inexpensive aqueous ammonia (28% NH3 in H2O) was used as the amino source.
One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols
Akai, Shuji,Ikawa, Takashi,Masuda, Shigeaki
supporting information, (2020/03/23)
Benzynes were selectively generated in situ from phenols and trapped regioselectively with potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group into a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize by using coupling reactions involving phenol derivatives with ammonia. Whereas reactions of ortho- and meta-substituted phenols produced meta-substituted anilines exclusively, those of para-substituted phenols provided ortho-silylanilines.
Design, synthesis and biological evaluation of hypolipidemic compounds based on BRD4 inhibitor RVX-208
Yu, Ping,Liu, Wenjing,Ren, Jinghui,Wang, Yingying,Ning, Yao,Huang, Mingqi,Hu,Wei, Lili,Ji, Min,Cai, Jin
, p. 2168 - 2172 (2019/07/03)
Bromodomain-containing protein 4 (BRD4) is a new therapeutic target for the treatment of diseases including cardiovascular diseases, cancer, inflammation and central nervous system (CNS) disorders. In this study, we introduced the pharmacophore of fibrates to a BRD4 inhibitor, RVX-208, to design dual-active hypolipidemic compounds, and found that some of new analogues showed favorable hypolipidemic activities. Synthetic accessibility towards this class of compounds optimized RVX-208 as well as would supply more thoughts on hypolipidemic drugs.
Coolade. A Low-Foaming Surfactant for Organic Synthesis in Water
Lee, Nicholas R.,Cortes-Clerget, Margery,Wood, Alex B.,Lippincott, Daniel J.,Pang, Haobo,Moghadam, Farbod A.,Gallou, Fabrice,Lipshutz, Bruce H.
, p. 3159 - 3165 (2019/04/26)
Several types of reduction reactions in organic synthesis are performed under aqueous micellar-catalysis conditions (in water at ambient temperature), which produce a significant volume of foam owing to the combination of the surfactant and the presence of gas evolution. The newly engineered surfactant “Coolade” minimizes this important technical issue owing to its low-foaming properties. Coolade is the latest in a series of designer surfactants specifically tailored to enable organic synthesis in water. This study reports the synthesis of this new surfactant along with its applications to gas-involving reactions.
Na2S-promoted reduction of azides in water: Synthesis of pyrazolopyridines in one pot and evaluation of antimicrobial activity
Kale, Ashok,Medishetti, Nagaraju,Kanugala, Sirisha,Ganesh Kumar,Atmakur, Krishnaiah
, p. 3186 - 3194 (2019/03/26)
Reduction of various azides using Na2S has been accomplished in water, and, in situ, the resulting amines on reaction with various ketones lead to pyrazolo[3,4-b]pyridines in one pot. Thus, a number of new trifluoromethyl-substituted pyrazolo[3,4-b]pyridine compounds have been prepared and screened for antimicrobial activity against different Gram-positive and Gram-negative strains. A good number of compounds, 4a, 4b, 4d, 4f, 4i, 4k, 4l, 4m, 4r and 4s, were found to possess promising activity. Notably, Na2S on hydrolysis in water generates H2S and NaOH, which facilitate the reduction of azides followed by intramolecular cyclization leading to the title compounds. To the best of our knowledge, this is the first report of the synthesis of the title compounds in aqueous medium in a one-pot reaction.
HETEROCYCLIC CARBOXYLIC ACID AMIDE LIGAND AND APPLICATIONS THEREOF IN COPPER CATALYZED COUPLING REACTION OF ARYL HALOGENO SUBSTITUTE
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Paragraph 0266-0267, (2019/05/15)
Provided are a heterocyclic carboxylic acid amide ligand and applications thereof in a copper catalyzed coupling reaction. Specifically, provided are uses of a compound represented by formula (I), definitions of radical groups being described in the specifications. The compound represented by formula (I) can be used as the ligand in the copper catalyzed coupling reaction of the aryl halogeno substitute, and is used or catalyzing the coupling reaction for forming the aryl halogeno substitute having C—N, C—O, C—S and other bonds.
Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides
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Page/Page column 89-90, (2020/01/09)
The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.
Based on BRD4 inhibitor RVX - 208 of the derivative and its preparation method and application (by machine translation)
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, (2018/09/21)
The invention discloses a method based on BRD4 inhibitor RVX - 208 of the derivative and its preparation method and application. Derivatives of the structure shown in formula I. The preparation method comprises: type 8 compound of formula 9 compound reaction, [...] 10 compound; type 10 compounds with malonic acid, d di-acid or fifth heavenly stem II acid after the reaction, with vinyl carbonate, 2 - halo of isobutyric acid or 4 - halo [...] butyric acid reaction; or, the type 10 compound directly with ethylene carbonate, 2 - halo of isobutyric acid or 4 - halo [...] butyric acid reaction. The invention also provides its application. The present invention provides based on BRD4 inhibitor RVX - 208 of the derivatives, can improve the activity or at the same time reducing cholesterol lowering cholesterol and triglyceride levels. (by machine translation)
