30100-35-7Relevant academic research and scientific papers
Metal-free, air-promoted, radical-mediated arylation of benzoquinone with phenylhydrazines
Sayahi, Mohammad Hosein,Ansari, Samira,Saghanezhad, Seyyed Jafar,Mahdavi, Mohammad
, p. 703 - 706 (2018)
An efficient, economic, and air-promoted metal-free method for direct arylation of benzoquinone with phenylhydrazines was developed. This approach leads to the formation of corresponding [1,1′-biphenyl]-2,5-dione derivatives as biological and pharmaceutic
Direct UV-written highly fluorinated aromatic-aliphatic copolyethers for optical waveguides
Wan, Ying,Zhang, Yang,Shi, Zuosen,Xu, Wenhui,Zhang, Xiaolong,Zhao, Lisha,Cui, Hanchen
, p. 967 - 975 (2012)
A bisphenol monomer (4-methoxy) phenylhydroquinone (Me-HQ) was prepared and further polymerized with 2,2,3,3,4,4,5,5,6,6,7,7-dodeca-fluoro-1,8-octanediol (12F-diol) and decafluorobiphenyl (DFBP) to obtain highly fluorinated aromatic-aliphatic copolyethers containing methoxy groups. After demethylation and the reaction with epoxy chloropropane, a series of novel highly fluorinated aromaticaliphatic copolyethers bearing epoxy groups (FA-APE EP) at different feed ratios of (Me-HQ)/(12F-diol) were obtained. The chemical structures of all the copolymers were analyzed by 1H NMR, 13C NMR and 19F NMR spectra. A series of highly fluorinated photoresists were prepared by composing of fluorinated copolyethers, diphenyliodonium salt as a photoacid generator (PAG) and solvent. After UV-curing, the cross-linked films exhibited excellent chemical resistance and high thermal stability (Td ranged from 230 to 278 -C). The refractive indices of the films could be controlled between 1.5127 and 1.4749 at 1550 nm by varying the feed ratio of comonomers. A clear negative pattern was obtained through direct UV exposure and chemical development. For waveguides without upper cladding, the propagation loss of the channel waveguides was measured to be 0.18 dB/cm at 1550 nm.
Chemoproteomics of an indole-based quinone epoxide identifies druggable vulnerabilities in vancomycin-resistant staphylococcus aureus
Kulkarni, Amogh,Soni, Isha,Kelkar, Dhanashree S.,Dharmaraja, Allimuthu T.,Sankar, Rathinam K.,Beniwal, Gaurav,Rajendran, Abinaya,Tamhankar, Sharvari,Chopra, Sidharth,Kamat, Siddhesh S.,Chakrapani, Harinath
supporting information, p. 6785 - 6795 (2019/08/20)
The alarming global rise in fatalities from multidrug-resistant Staphylococcus aureus (S. aureus) infections has underscored a need to develop new therapies to address this epidemic. Chemoproteomics is valuable in identifying targets for new drugs in different human diseases including bacterial infections. Targeting functional cysteines is particularly attractive, as they serve critical catalytic functions that enable bacterial survival. Here, we report an indole-based quinone epoxide scaffold with a unique boat-like conformation that allows steric control in modulating thiol reactivity. We extensively characterize a lead compound (4a), which potently inhibits clinically derived vancomycin-resistant S. aureus. Leveraging diverse chemoproteomic platforms, we identify and biochemically validate important transcriptional factors as potent targets of 4a. Interestingly, each identified transcriptional factor has a conserved catalytic cysteine residue that confers antibiotic tolerance to these bacteria. Thus, the chemical tools and biological targets that we describe here prospect new therapeutic paradigms in combatting S. aureus infections.
C-H arylation reactions through aniline activation catalysed by a PANI-g-C3N4-TiO2 composite under visible light in aqueous medium
Wang, Liang,Shen, Jun,Yang, Sen,Liu, Wenjie,Chen, Qun,He, Mingyang
supporting information, p. 1290 - 1296 (2018/03/26)
A PANI (polyaniline)-g-C3N4-TiO2 composite was prepared and found to be efficient for radical C-H arylation reactions. The arylation process involved coupling of in situ generated aryl diazonium salts from aniline with heteroarenes, enol acetates or benzoquinones under visible light in aqueous medium or pure water. A broad range of substrates survived the reaction conditions to provide the desired products in moderate to good yields. Scale-up (10 mmol) synthesis was also achieved. This semiconductor photocatalyst showed good photocatalytic performance and stability. Recycle studies showed that this composite could be readily recovered and a slight decrease in the catalytic activity was observed after ten consecutive runs.
Hydroquinone-Based Biarylic Polyphenols as Redox Organocatalysts for Dioxygen Reduction: Dramatic Effect of Orcinol Substituent on the Catalytic Activity
Lebeuf, Rapha?l,Nardello-Rataj, Véronique,Aubry, Jean-Marie
, p. 268 - 278 (2017/02/05)
A series of 18 new biaryls has been synthesized and investigated with regard to their organocatalytic efficiency. They consist of a hydroquinone core linked to a phenol or a resorcinol moiety. It is shown that the resorcinol moiety substituted on its meta position has a strong impact on the catalytic activities of these compounds towards the reduction of dioxygen by diethylhydroxylamine (DEHA) in aqueous medium. While the derivative consisting of the two cores spaced by three methylene units is completely inactive, substitution on the hydroquinone part leads to tremendously active catalysts, especially the biaryl consisting of methoxyhydroquinone-orcinol. Two mechanisms are proposed to explain the dramatic efficiency of the novel hydroquinone-based biarylic polyphenols for the catalytic reduction of dioxygen, both considering the influence of the orcinol moiety on the semiquinone anion intermediate. As a first hypothesis, this substituent could promote its direct reduction by DEHA to regenerate the hydroquinone, which will react again to regenerate the semiquinone. On the other hand, an intramolecular hydrogen bond could enhance the reactivity of the semiquinone anion toward dioxygen by an addition–elimination mechanism. In this case, the elimination would provide the corresponding quinone but, since the reduction of the quinones by DEHA is much slower than the observed kinetics, a reduction by DEHA prior to the elimination has to be considered to generate the semiquinone anion instead of the quinone. (Figure presented.).
Ir-catalyzed arylation, alkylation of quinones with boronic acids through C-C coupling
Wang, Dawei,Ge, Bingyang,Ju, Anqi,Zhou, Yucheng,Xu, Chongying,Ding, Yuqiang
supporting information, p. 30 - 33 (2015/01/30)
Ir-catalyzed arylation, alkylation of quinones with boronic acids was developed under room temperature. Both aryl and alkyl boronic acids are suitable for this transformation. This expands the application scope of the iridium catalyst. This is also an excellent proof that iridium catalysts can be used in the C-C coupling of quinones and naphthoquinones with alkyl boronic acids.
Synthesis of aryl substituted quinones as β-secretase inhibitors: Ligand-free direct arylation of quinones with aryl halides
Wang, Dawei,Ge, Bingyang,Yang, Shuyan,Miao, Hongyan,Ding, Yuqiang
, p. 1615 - 1621 (2015/02/19)
The simple ligand-free direct arylation of quinones with aryl halides applying Pd(OAc)2as a catalyst in accordance with Heck reaction was studied. This reaction provided a simple and efficient synthetic approach to efficient inhibitors of β-secretase aryl-substituted quinones.
Transition metal-free direct C-H functionalization of quinones and naphthoquinones with diaryliodonium salts: Synthesis of aryl naphthoquinones as β-secretase inhibitors
Wang, Dawei,Ge, Bingyang,Li, Liang,Shan, Jie,Ding, Yuqiang
, p. 8607 - 8613 (2015/01/08)
A novel ligand-free, transition metal-free direct C.H functionalization of quinones with diaryliodonium salts has been developed for the first time. The transformation was promoted only through the use of a base and gave aryl quinone derivatives in moderate to good yields. This methodology provided an effective and easy way to synthesize β-secretase inhibitors. The radical trapping experiments showed that this progress was the radical mechanism.
Generation of arylated quinones by iron-catalyzed oxidative arylation of phenols: Formal synthesis of phellodonin, sarcodonin ε, leucomelone and betulinan A
Deb, Arghya,Agasti, Soumitra,Saboo, Tapish,Maiti, Debabrata
supporting information, p. 705 - 710 (2014/04/03)
Biologically and pharmaceutically relevant arylated quinones (Quin-Ar) have been synthesized via direct C-H arylation of a variety of phenols using arylboronic acids. An inexpensive, environmentally friendly iron catalyst, ferric sulphate, Fe2(SO4)3, was employed in this operationally simple and efficient method.
Palladium-catalyzed direct C-H functionalization of benzoquinone
Walker, Sarah E.,Jordan-Hore, James A.,Johnson, David G.,MacGregor, Stuart A.,Lee, Ai-Lan
supporting information, p. 13876 - 13879 (2015/02/05)
A direct Pd-catalyzed C-H functionalization of benzoquinone (BQ) can be controlled to give either mono- or disubstituted BQ, including the installation of two different groups in a one-pot procedure. BQ can now be directly functionalized with aryl, heteroaryl, cycloalkyl, and cyclo-alkene groups and, moreover, the reaction is conducted in environmentally benign water or acetone as solvents.
