17583-00-5Relevant academic research and scientific papers
Substituted conformationally restricted guanidine derivatives: Probing the α2-adrenoceptors’ binding pocket
McMullan, Michela,García-Bea, Aintzane,Miranda-Azpiazu, Patricia,Callado, Luis F.,Rozas, Isabel
, p. 48 - 57 (2016)
In this paper we report the design, synthesis and pharmacological evaluation of new N-substituted 2-amino-1,4-dihydroquinazolines, 2-amino-1,4-dihydropyridopyrimidines and 2-amino-4,5-dihydro-1,3-benzodiazepines as α2-adrenoceptors ligands. Computational studies show that the proposed substitutions and guanidine-containing ring size will probe an extensive area of the active site. Preparation of these molecules involved novel routes than those previously utilised in our laboratory for the preparation of the acyclic aryl-guanidine counterparts. Compounds 8b and 18c showed the highest affinity and antagonistic activity, within their series, towards the α2-adrenoceptor in human brain tissue in?vitro experiments. Structure-activity relationships have been established for the design and biological evaluation of novel α2-adrenoceptor ligands.
Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions
Walker, Benjamin R.,Manabe, Shuhei,Brusoe, Andrew T.,Sevov, Christo S.
supporting information, p. 6257 - 6265 (2021/05/07)
Simple copper salts serve as catalysts to effect C-X bond-forming reactions in some of the most utilized transformations in synthesis, including the oxidative coupling of aryl boronic acids and amines. However, these Chan-Lam coupling reactions have historically relied on chemical oxidants that limit their applicability beyond small-scale synthesis. Despite the success of replacing strong chemical oxidants with electrochemistry for a variety of metal-catalyzed processes, electrooxidative reactions with ligandless copper catalysts are plagued by slow electron-transfer kinetics, irreversible copper plating, and competitive substrate oxidation. Herein, we report the implementation of substoichiometric quantities of redox mediators to address limitations to Cu-catalyzed electrosynthesis. Mechanistic studies reveal that mediators serve multiple roles by (i) rapidly oxidizing low-valent Cu intermediates, (ii) stripping Cu metal from the cathode to regenerate the catalyst and reveal the active Pt surface for proton reduction, and (iii) providing anodic overcharge protection to prevent substrate oxidation. This strategy is applied to Chan-Lam coupling of aryl-, heteroaryl-, and alkylamines with arylboronic acids in the absence of chemical oxidants. Couplings under these electrochemical conditions occur with higher yields and shorter reaction times than conventional reactions in air and provide complementary substrate reactivity.
COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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Paragraph 0335; 0437-0443, (2020/08/28)
The present invention relates to a device for emitting light. Provided are a novel mixture capable of improving stability and longevity, an organic electronic element using the same, and an electronic device thereof. (by machine translation)
Synthesis method of N-phenyl aminobenzoic acid
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Paragraph 0007; 0027-0030; 0033-0036; 0039-0042; 0045-0047, (2021/01/11)
The invention belongs to the technical field of organic intermediate synthesis, and particularly relates to a synthesis method of N-phenyl aminobenzoic acid. The method comprises the following steps:(1) dissolving 2-chlorobenzonitrile and aniline in a solvent, adding K2CO3 and NaOH while stirring, and heating to carry out primary reflux reaction; (2) after the reflux reaction is finished, recovering the solvent under reduced pressure, then cooling the residual liquid, adding water, and heating to carry out secondary reflux reaction; and (3) cooling the reaction solution after the secondary reflux reaction in the step (2) to room temperature, extracting excessive aniline, adding diluted hydrochloric acid for neutralization while stirring a water phase, separating out a solid, filtering, and recrystallizing to obtain the target product N-phenyl aminobenzoic acid. According to the method, a one-pot process is adopted, under the condition that a catalyst is not used, 2-chlorobenzonitrileand aniline are used as raw materials for reaction, the target product with high purity (larger than 99%) and high yield (larger than 90%) is obtained, operation is easy, the raw materials are easy toobtain, the reaction is mild and easy to control, and aftertreatment is simple.
CuSO4-Catalyzed dual annulation to synthesize O, S or N-containing tetracyclic heteroacenes
Kang, Yan-Biao,Qu, Jian-Ping,Shan, Xiang-Huan,Yang, Bo
supporting information, p. 4063 - 4066 (2020/04/20)
In this work, CuSO4 is utilized as a practical redox catalyst for tandem dual annulation in the synthesis of indole-fused tetracyclic heteroacenes, which are important skeletons in both medicinal chemistry and materials chemistry. The preparation of such skeletons in a convenient and efficient manner is in high demand. This method realizes the modular synthesis of benzofuro-, benzothieno-, and indoloindoles from abundant feedstocks such as 2-halobenzyl halides and nitrile derivatives in up to 99% yields, providing a rapid access to diverse indole-fused heteroacenes with biological or optoelectronic properties.
Reductive Molybdenum-Catalyzed Direct Amination of Boronic Acids with Nitro Compounds
Suárez-Pantiga, Samuel,Hernández-Ruiz, Raquel,Virumbrales, Cintia,Pedrosa, María R.,Sanz, Roberto
supporting information, p. 2129 - 2133 (2019/01/25)
The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C?N coupling. Our methodology has proven to be scalable, air and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds. Moreover, this general and step-economical synthesis of aromatic secondary amines showcases orthogonality to other aromatic amine syntheses as it tolerates aryl halides and carbonyl compounds.
CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides
Mohammadinezhad, Arezou,Akhlaghinia, Batool
, p. 15525 - 15538 (2019/10/19)
In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.
Pd/AlO(OH): A Heterogeneous, Stable and Recyclable Catalyst for N-Arylation of Aniline Under Ligand-Free Aerobic Condition
Ganesh Babu, Sundaram,Emayavaramban, Balakumar,Jerome, Peter,Karvembu, Ramasamy
, p. 2619 - 2629 (2017/09/06)
Abstract: Many synthetic methods have been reported to construct an aryl-nitrogen bond. But they mainly suffer from the usage of expensive ligands. Herein, we report highly effective, heterogeneous, reusable and ligand-free nanocatalyst for the Buchwald-Hartwig coupling reaction under aerobic condition. Wafer-like structure with nano-porous nature of AlO(OH) was identified with TEM and BET surface area analyses. Zero valent Pd nanoparticles (with less than 10?nm crystallite size which strongly evident from TEM analysis) were observed in XRD pattern, which was further confirmed by XPS studies. The reaction conditions were optimized and the scope of the reaction was extended with various aryl halides and aniline using low amount of Pd (0.31?mol%) based heterogeneous catalyst. Heterogeneity, reusability and stability (confirmed by XRD) were found to be reasonable. Use of meagre amount of Pd and the ligand-free aerobic condition make this system economically as well as environmentally feasible. Graphical Abstract: [Figure not available: see fulltext.].
A Copper-Catalyzed Tandem C–H ortho-Hydroxylation and N–N Bond-Formation Transformation: Expedited Synthesis of 1-(ortho-Hydroxyaryl)-1H-indazoles
Chen, Cheng-Yi,He, Fengxian,Tang, Guangrong,Ding, Han,Wang, Zhaobin,Li, Dawei,Deng, Lujiang,Faessler, Roger
supporting information, p. 6604 - 6608 (2017/12/04)
A facile, one-pot synthesis of 1H-indazoles featuring a Cu-catalyzed C–H ortho-hydroxylation and N–N bond-formation sequence with the use of pure oxygen as the terminal oxidant was developed. The reaction of readily available 2-arylaminobenzonitriles with
A Synthesis of 1H-Indazoles via a Cu(OAc)2-Catalyzed N-N Bond Formation
Chen, Cheng-Yi,Tang, Guangrong,He, Fengxian,Wang, Zhaobin,Jing, Hailin,Faessler, Roger
supporting information, p. 1690 - 1693 (2016/04/26)
A facile synthesis of 1H-indazoles featuring a Cu(OAc)2-catalyzed N-N bond formation using oxygen as the terminal oxidant is described. The reaction of readily available 2-aminobenzonitriles with various organometallic reagents led to o-aminoar
