573-97-7Relevant articles and documents
Regioselective C(sp2)?C(sp3) Oxidative Bond Cleavage of 1-(1-Hydroxyalkyl) naphthalen-2-ols: First Synthesis of 1-Azido-halo-naphthalene-2(1H)-ones
Kumar Ghosh, Manoj,Roy, Barnali,Sarkar, Debayan
, p. 327 - 331 (2021)
A new one-pot oxidative cleavage of C(sp2)?C(sp3) bond has been explored using two complementary protocols employing Phenylselenyl bromide (PhSeBr) as well as Phenyltrimethylammonium Tribromide (PTAB), with much greater efficiency and scope. The oxidative cleavage proceeds via a dearomatization step to afford potentially useful bromonaphthols along with corresponding aldehydes. In this course, we also described the first synthesis of synthetically important azido-halo naphthaleneones.
Facile synthesis of 1-(arylimino)naphthalen-2(1H)-ones from anilines and 2-naphthols promoted by NaBr/K2S2O8/CAN
Yu, Fei,Xu, Hui,Asiri, Abdullah M.,Marwani, Hadi M.,Zhang, Ze
, p. 704 - 714 (2019)
An efficient method has been developed for the synthesis of 1-(arylimino)naphthalen-2(1H)-ones through the cascade reaction of anilines and 2-naphthols promoted by NaBr/K2S2O8/Ce(NH4)2(NO3)6. Using this protocol, a series of 1-(arylimino)naphthalen-2(1H)-ones was obtained in good to excellent yields (17 examples, 70–92% yields). The reactions may proceed through the following steps: bromination of 2-naphthols by in-situ-generated bromine from NaBr and K2S2O8 to afford 1-bromonaphthalen-2-ols, coupling of 1-bromonaphthalen-2-ols with anilines to afford the corresponding amines, and subsequent oxidation of the amines into the products by Ce(NH4)2(NO3)6. These newly obtained α-imine ketones have great potentials for synthesis of special optical materials bearing naphthalene moiety.
ION CHANNEL ANTAGONISTS/BLOCKERS AND USES THEREOF
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Page/Page column 22; 24; 53, (2021/06/22)
Provided are ion channel antagonists/blockers and uses thereof. Specifically, it provides the compounds of formula (I) or pharmaceutically acceptable salts, stereoisomers, solvates or prodrugs, preparation method therefor and application thereof. Definition of each group in the formula can be found in the specification for details. Provided is also pharmaceutical composition useful for treatment of heart disease and other ion channel related diseases.
Transition-metal- and phosphorus-free electrophilic trifluoromethylthiolation of indoles with sodium trifluoromethanesulfinates in ionic liquids
Wang, Fei,Lu, Guo-Ping,Lin, Yamei
, (2021/04/12)
An acid-promoted protocol has been developed to achieve the transition-metal- and phosphorus-free electrophilic trifluoromethylthiolation of indoles using sodium trifluoromethanesulfinates in an imidazolium-based ionic liquid ([Hmim]Br). [Hmim]Br not only acts as a recyclable solvent, but also as the reductant in this transformation. The advantages of this chemistry include simple operation, use of a recyclable solvent, avoidance of transition-metal and phosphorus, and gram-scale synthesis.
Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis
He, Xinxin,Wang, Xinyan,Tse, Ying-Lung Steve,Ke, Zhihai,Yeung, Ying-Yeung
, p. 12632 - 12642 (2021/10/21)
Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in the activation of imine and carbonyl groups in various transformations with good yields and selectivity. Lewis acidity of the bis-selenonium salts was found to be stronger than that of the monoselenonium systems, attributed to the synergistic effect of the two cationic selenonium centers. In addition, the bis-selenonium catalysts are not inhibited by strong bases or moisture.
Bromination of phenyl ether and other aromatics with bromoisobutyrate and dimethyl sulfoxide
Li, Jia-Qin,Chen, Xiao-Hui,Wang, Xian-Xun,Cui, Hai-Lei
supporting information, (2021/09/09)
Bromoisobutyrate has been used for the first time as a general brominating source for the direct bromination of a diverse of simple phenyl ethers. Aromatic ethers bearing various substituents could be compatible in this reaction system delivering brominated arenes in moderate to good yields. The reaction system can also be expanded to bromination of phenols and unactivated arene. This process can be regarded as an alternative for the well-established bromination systems for bromoarene synthesis.
Electrochemical C-H Halogenations of Enaminones and Electron-Rich Arenes with Sodium Halide (NaX) as Halogen Source for the Synthesis of 3-Halochromones and Haloarenes
Jin, Jun,Lin, Yan,Liu, Yunyun,Wan, Jie-Ping,Wang, Chaoli
, p. 12378 - 12385 (2021/09/07)
Without employing an external oxidant, the simple synthesis of 3-halochromones and various halogenated electron-rich arenes has been realized with electrode oxidation by employing the simplest sodium halide (NaX, X = Cl, Br, I) as halogen source. This electrochemical method is advantageous for the simple and mild room temperature operation, environmental friendliness as well as broad substrate scope in both C-H bond donor and halogen source components.
Catalytic Enantioselective Synthesis of Axially Chiral Diarylmethylidene Indanones
Kumar, Prashant,Shirke, Rajendra P.,Yadav, Sonu,Ramasastry
supporting information, p. 4909 - 4914 (2021/06/30)
We describe the first atropselective Suzuki-Miyaura cross-coupling of β-keto enol triflates to access axially chiral (Z)-diarylmethylidene indanones (DAIs). The chemical, physical, and biological properties of DAIs are unknown, despite their being structurally similar to arylidene indanones, primarily due to the lack of racemic or chiral methods. Through this work, we demonstrate a general and efficient protocol for the racemic as well as the atropselective synthesis of (Z)-DAIs. An unusual intramolecular Morita-Baylis-Hillman reaction is utilized for the Z-selective synthesis of β-keto enol triflates.
Evaluation of a Continuous-Flow Photo-Bromination Using N -Bromosuccinimide for Use in Chemical Manufacture
Waterford, Matthew,Saubern, Simon,Hornung, Christian H.
, p. 569 - 573 (2021/04/16)
A continuous-flow photo-bromination reaction on benzyl and phenyl groups was conducted using N-bromosuccinimide as the bromine source inside a preparatory-scale glass plate reactor. This flow reactor system was capable of independently controlling light intensity, wavelength, and reaction temperature, hence exerting an exceptional level of control over the reaction. A short optimisation study for the synthesis of 2-bromomethyl-4-trifluoromethoxyphenylboronic acid pinacol ester resulted in best conditions of 20°C and 10 min residence time using an LED (light-emitting diode) array at 405 nm and acetonitrile as the solvent. The present study evaluates the potential for this easy-to-handle bromination system to be scaled up for chemical manufacture inside a continuous-flow glass plate reactor. The combination with an in-line continuous flow liquid-liquid extraction and separation system, using a membrane separator, demonstrates the potential for continuous flow reaction with purification in an integrated multi-stage operation with minimal manual handling in between.
Method for preparing bromo reagent by oxidative bromination reaction and method for further preparing bromine-containing compound
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Paragraph 0030-0031, (2020/03/17)
The invention relates to a method, and for preparing a bromine-containing compound through a reaction, of a :electron-substituted furan compound.rich electron-substituted furan compound, rich in an electron-rich substituted thiophene compound: The substituent of,rich electron-substituted furan compound containing, of an electron-rich substituted furan compound . The method for preparing the bromine-containing compound by the reaction of the present invention comprises the following steps. preparing an electron-rich substituted furan), compound (by). reacting with a bromine, containing substituted phenyl group, (.rich, electron-substituted furan compound and an aromatic or unsaturated bond-containing compound with an electron-rich substituted furan compound containing an electron-rich substituted furan compound.
