3217-15-0Relevant academic research and scientific papers
Columnar Propeller-Like 1,3,5-Triphenylbenzenes: Probing the Effect of Chlorine on the Suzuki Cross-Coupling and Liquid Crystalline Properties
Grunwald, Marco André,W?hrle, Tobias,Forschner, Robert,Baro, Angelika,Laschat, Sabine
supporting information, p. 2190 - 2198 (2020/03/03)
Suzuki cross-couplings either between chlorinated N-methyliminodiacetic acid (MIDA)-protected aryl boronates and 1,3,5-tribromobenzene or between chlorinated aryl bromides and phenyltrisboronic species to star-shaped 1,3,5-triphenylbenzenes with different substitution patterns and chloro substituents at the outer phenyl rings were studied. The chlorinated precursors required for the respective reaction were synthesized and characterized. Depending on the used coupling reaction target triphenylbenzenes were isolated in yields between 42 % and 88 %. Their mesomorphic properties were influenced by the substitution pattern and number of peripheral chlorine atoms. Triphenylbenzene with 3,5-alkoxy substitution and H in para-position self-assembled into either columnar hexagonal (Colh) mesophases or a soft crystal. While threefold chloro substitution in meta-position of the outer phenyl rings led to stable room temperature Colho phases, triphenylbenzenes with threefold para-chloro or 3,5-dichloro substitution were non-mesomorphic. Based on X-ray diffraction data a helical packing model for the observed phases similar to that of related alkoxy-substituted triphenylbenzenes was proposed.
7-benzyl-4-(4-phenylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine derivatives and Composition for skin whitening and Pharmaceutical composition for use in preventing or treating disorders of Melanin Hyperpigmentation containing the same as an active ingredient
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Paragraph 0218-0222, (2020/11/06)
The present invention relates to a 7-benzyl-4(4-phenylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine derivative, and to a composition for skin whitening, comprising the same as an active ingredient. Since the derivative exhibits the effect of inhibiting the production of melanin even when used in a small amount, it is useful as a pharmaceutical composition for preventing or treating melanin hyperpigmentation diseases, a cosmetic composition for skin whitening, and a health functional food for skin whitening.
Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium
Tomanová, Monika,Jedinák, Luká?,Canka?, Petr
supporting information, p. 2621 - 2628 (2019/06/03)
Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromides and iodides, or dehalogenative sulfonation of (hetero)aryl chlorides and fluorides, using sodium sulfite as the sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalyst and avoids using organic solvent as the reaction medium. This method is especially suitable for substrates that readily tautomerize (such as 2-or 4-halogenated aminophenols and 4-halogenated resorcinols), for which dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfite is an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three potential applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a reducing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardous and corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into less harmful compounds.
1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane: An efficient and high oxygen content oxidant in various oxidative reactions
Khosravi, Kaveh,Naserifar, Shirin
supporting information, p. 6584 - 6592 (2018/10/05)
Several oxidative approaches namely thiocyanation of aromatic compounds, epoxidation of alkenes, amidation of aromatic aldehydes, epoxidation of α β-unsaturated ketones, oxidation of sulfides to sulfoxides and sulfones, bayer-villeger reaction, bromination and iodation of aniline and phenol derivatives oxidative esterification, oxidation of pyridines and oxidation of secondary, allylic and benzyllic alcohols were carried out using 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as the potential solid oxidant which can be stored for several months without any loss in its activity. All of the procedures were accomplished via mild reaction conditions and the products were afforded in high yields and short reaction times.
Regioselective C-H chlorination: Towards the sequential difunctionalization of phenol derivatives and late-stage chlorination of bioactive compounds
Gao, Chao,Li, Hongchen,Liu, Miaochang,Ding, Jinchang,Huang, Xiaobo,Wu, Huayue,Gao, Wenxia,Wu, Ge
, p. 46636 - 46643 (2017/10/16)
We have developed a protocol for the auxillary directed C-H chlorination of phenol derivatives using catalytic amounts of palladium acetate that is amenable to the late-stage chlorination of diflufenican and estrone. The 2-pyridine group allows for a highly efficient palladium-catalyzed chlorination and sequential ortho C-H functionalization reaction of phenol derivatives to produce a variety of symmetrical and unsymmetrical 2,4,6-trisubstituted phenols.
BORON-CONTAINING SMALL MOLECULES
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Paragraph 0294; 0295, (2013/06/04)
This invention provides novel compounds, methods of using the compounds, and pharmaceutical formulations comprising the compounds.
Green, mild and efficient bromination of aromatic compounds by HBr promoted by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane in water as a solvent
Khosravi, Kaveh,Kazemi, Samira
experimental part, p. 387 - 390 (2012/05/20)
A combination of HBr and trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as a new and powerful oxidant was found effective for facile bromination of different aromatic compounds at room temperature in water as a green solvent. Mild reaction conditions, high selectivity and yield, high reaction rate and non-toxicity are some of the major advantages of this synthetic protocol.
Regioselective bromination and iodination of aromatic substrates promoted by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane
Azarifar, Davood,Khosravi, Kaveh,Najminejad, Zohreh,Soleimani, Khadijeh
experimental part, p. 321 - 326 (2012/08/14)
Selective and efficient bromination and iodination of aromatic compounds by ammonium bromide and ammonium iodide, respectively, under promotion of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane have been explored. Mild reaction conditions, high selectivity and yield, and high reaction rate are some of the major advantages of this synthetic method.
Regioselective bromination of activated aromatic substrates with a ZrBr4/diazene mixture
Stropnik, Tadej,Bombek, Sergeja,Ko?evar, Marijan,Polanc, Slovenko
, p. 1729 - 1733 (2008/09/18)
A regioselective method for the bromination of phenols, ethers and anilines using a ZrBr4/diazene mixture is described. The reaction takes place under mild reaction conditions and the bromine atom adds first at the para unsubstituted position with respect to the OH, OR or NR2 group of the activated aromatic substrate. Less reactive compounds such as toluene, phenyl acetate, benzonitrile and trifluoromethylbenzene remain intact under the same conditions.
INDOLE DERIVATIVES AND THEIR USE AS THYROID RECEPTOR LIGANDS
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Page/Page column 32, (2008/06/13)
The invention provides compounds of formula (I) or pharmaceutically acceptable esters, amides, solvates or salts thereof, including salts of such esters or amides, and solvates of such esters, amides or salts, (I) wherein R1, R2, R3, R4, R5, R6, Y and W are as defined in the specification. The invention also provides the use of such compounds in the treatment or prophylaxis of a condition that may be treated with a thyroid receptor agonist or partial agonist.
