- Iridium-Catalyzed C(sp3)?H Addition of Methyl Ethers across Intramolecular Carbon–Carbon Double Bonds Giving 2,3-Dihydrobenzofurans
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Intramolecular addition of an O-methyl C(sp3)?H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of methyl 2-(propen-2-yl)phenyl ethers. The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110–135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans. Enantioselective C(sp3)?H addition is achieved in the reaction of methyl 2-(1-siloxyethenyl)phenyl ethers, affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives with up to 96% ee. (Figure presented.).
- Ohmura, Toshimichi,Kusaka, Satoshi,Torigoe, Takeru,Suginome, Michinori
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supporting information
p. 4448 - 4453
(2019/09/16)
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- Synthesis method for aromatic ring bromination of acetophenones derivative
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The invention relates to a synthesis method for aromatic ring bromination of an acetophenones derivative, and belongs to the technical field of organic synthesis. The synthesis method consists of twokinds of synthesis methods: method A, adding the acetophenone derivative into a first oxidizing agent and stirring to form a suspension system, controlling the temperature of the suspension system tobe 10-50 DEG C, adding a first reducing agent or a second reducing agent, stirring and reacting for 2-20 h, and performing aftertreatment after the reaction is completed to obtain the aromatic ring brominated acetophenone derivative; method B, adding the acetophenone derivative into the second reducing agent and stirring to form a suspension system, controlling the temperature of the suspension system to be 10-50 DEG C, then adding a second oxidizing agent or the first oxidizing agent, stirring and reacting for 2-20 h, and performing aftertreatment after the reaction is completed to obtain thearomatic ring brominated acetophenone derivative. According to the synthesis method provided by the invention, an inorganic and non-toxic bromination reagent is used, water is used as a reaction solvent, the prepared product is mutually incompatible with water, so that separation and the aftertreatment are convenient to perform, therefore, the synthesis method of the invention is applicable to large-scale industrial production of intermediate products for aromatic ring bromination of the acetophenones derivative.
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Paragraph 0067-0070
(2019/06/11)
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- Magnesium tetrapyrazinoporphyrazines: Tuning of the pKa of red-fluorescent pH indicators
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Magnesium(ii) tetrapyrazinoporphyrazines (TPyzPzs) are excellent red fluorophores (λF ～ 663 nm, ΦF ～ 0.53 in THF). In this work, a series of magnesium(ii) complexes of unsymmetrical TPyzPzs bearing one or two phenol substituents was prepared. Suitable substitutions on the phenolic moiety tuned its pKa in the range of 5.5 to 13. Deprotonation of the phenolic group at higher pH induced a strong donor (phenolate) in the macrocycle that led to pH-dependent quenching of the red fluorescence of these indicators. pH sensing was proved in water solutions after the incorporation of TPyzPzs into two delivery systems-microemulsions and liposomes. The latter also serves as a simple model of biomembranes. Finally, a wavelength-ratiometric probe was constructed by the incorporation of a TPyzPz indicator and lipophilic pH-nonsensitive BODIPY dye into liposomes. Synthetic precursors for TPyzPzs, substituted pyrazine-2,3-dicarbonitriles, also represent donor-acceptor systems and the pH-dependent changes in absorption spectra may be easily visible to the naked eye.
- Karlikova, Martina,Cermakova, Veronika,Demuth, Jiri,Valer, Vojtech,Miletin, Miroslav,Novakova, Veronika,Zimcik, Petr
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supporting information
p. 6162 - 6173
(2019/05/16)
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- Photocatalytic benzene and benzene derivative direct hydroxylation or amination method
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The invention discloses a photocatalytic benzene and benzene derivative direct hydroxylation or amination method. The method is characterized by comprising the following steps: (1) adding a photo-sensitizer and a cobalt catalyst into a solvent to obtain a solution (A); (2) adding benzene (or benzene derivatives), water, ammonia gas, and amide derivatives (or sulfonamide derivatives) into the solution (A) to obtain a solution (B); and (3) in a N2 (or Ar) environment, radiating the solution (B) by a medium pressure mercury lamp, a high pressure mercury lamp, a xenon lamp, or an LED lamp to obtain phenols or amines and H2. For the first time, a photo-sensitizer and a cobalt catalyst are combined and applied to photocatalytic hydroxylation and amination of benzene. The conditions of the method are mild, light is taken as the driving energy, no oxidant is added, the only byproduct is H2, and the whole process is green, concise, and efficient. High selective benzene one-step hydroxylation to generate phenol or high selective phenol/benzene one-step amination to generate aniline is realized, and the method can be applied to the production of phenol and aniline.
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Paragraph 0130-0131
(2017/11/29)
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- Dependence of mesomorphism on flexibility of lateral and terminal groups of chalconyl esters
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A novel liquid crystalline homologous series of chalconyl vinyl esters with a lateral bromo substituent RO─C6H4─CH═CH─COO─C6H3─(Br)─CO-CH═CH─C6H4─C12H25(n) has been synthesized and studied with a view to understanding and establishing the relation between the molecular structure and liquid crystal (LC) behavior in terms of molecular flexibility of the lateral and terminal groups. The novel homologous series consists of thirteen (C1–C18) homologues, whose enantiotropic nematic and smectic mesomorphism commences from the C4, (C4–C18) and the C5, (C5–C18) homologue, respectively. The rest of the homologues (C1, C2, C3) are nonliquid crystals (NLC). Mesomorphism and transition temperatures were examined using an optical polarising microscope (POM) equipped with a heating stage. Textures of nematic phase are threaded or Schlieren and those of the Smectic-A or Smectic-C are focal conic. Analytical, thermal and spectral data supported molecular structures of the novel homologues. Thermal for smectic and nematic are 87.5°C and 101.1°C, respectively, whose, total mesophase length ranges from 17°C to 30°C at C14 and C7 homologue, respectively. The mesomorphic transition temperature ranges are between 70°C and 113°C.
- Patel, Priya K.,Shah
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- TETRAZOLINONE COMPOUND AND APPLICATIONS THEREOF
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Disclosed is a tetrazolinone compound having a high pest control effect and represented by the formula (1): wherein R1, R2, R3, and R11 each represent a halogen atom, a C1-C6 alkyl group, or the like; R4 and R5 each represent a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or the like; R6 represents a C1-C3 alkyl group which may have a halogen atom(s) or the like; R7, R8, and R9 each represent a hydrogen atom, a halogen atom, or the like; R10 represents a C1-C3 alkyl group or the like; R12 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, or the like, and R13 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, or the like.
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Paragraph 0834; 0867
(2015/11/24)
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- An eco-friendly Co(OAc)2-catalyzed aerobic oxidation of 4-benzylphenols into 4-hydroxybenzophenones
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An undecorated Co(OAc)2-catalyzed aerobic oxidation system has been reported that enables direct transformation of 4-benzylphenols into the corresponding 4-hydroxybenzophenones. The procedure is especially suitable for electron-withdrawing group-containing substrates, which are commonly inefficient to conduct this category of oxidation. Based on well-defined p-benzoquinone methides and the confirmed ethereal intermediate, a plausible mechanism was depicted.
- Huang, Jian-Gang,Guo, Ying,Jiang, Jian-An,Liu, Hong-Wei,Ji, Ya-Fei
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p. 7115 - 7124
(2015/02/19)
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- Poly(4-vinylpyridinium bromochromate): An efficient reagent for bromination of aromatic compounds
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A simple and efficient method for the bromination of various aromatic compounds by using poly(4-vinylpyridinium bromochromate) is reported. This method has several advantages such as good selectivity between ortho and para positions of aromatic compounds, simple workup, short reaction times, and high yields of the products.
- Albadi, Jalal,Tajik, Hassan,Keshavarz, Mosadegh,Abedini, Masoumeh
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p. 179 - 181
(2013/07/27)
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- METHYLPYRROLOPYRIMIDINECARBOXAMIDES
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The compounds of Formula (I), wherein R1, R2, R21, R22, R23, R24, Y and R3 have the meanings as given in the description, the salts thereof, the stereoisomers of the compounds and the salts thereof are effective inhibitors of the type 5 phosphodiesterase.
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Page/Page column 104
(2012/06/18)
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- METHYLPYRROLOPYRIMIDINECARBOXAMIDES
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The compounds of formula (I) wherein R1, R2, R21, R22, R23, R24, Y and R3 have the meanings as given in the description, the salts thereof, and the stereoisomers of the compounds and the salts thereof are effective inhibitors of the type 5 phosphodiestera
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Page/Page column 166
(2011/04/14)
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- BIARYL OXYACETIC ACID COMPOUNDS
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Some embodiments of the present invention include novel phenoxyacetic acids useful for the prevention and treatment of inflammatory disorders, including those affecting the respiratory system and skin. Some compounds provided include those of the general formula (I), and compounds of general formula (Ia).
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Page/Page column 51
(2011/02/24)
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- BIARYL OXYACETIC ACID COMPOUNDS
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The present invention provides biaryl oxyacetic acid compounds which may be useful for treating inflammatory disorders, including disorders affecting the respiratory system and skin. The compounds provided include those of the general formula I.
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Page/Page column 48-49
(2010/09/18)
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- Studies towards the synthesis of 13C-labelled anthocyanins
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The anthocyanins are a class of polyphenols found in nature, which are widely distributed throughout the plant kingdom and are thought to possess antioxidant properties. Methodology previously developed in our group for the regioselective placement of 13C-atoms into aromatic rings is being applied to the synthesis of 13C-labelled anthocyanins-namely cyanidin-3-glucoside and delphinidin-3-glucoside. Copyright
- Marshall, Laura J.,Cable, Karl M.,Botting, Nigel P.
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scheme or table
p. 315 - 318
(2011/05/02)
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- Tetrameric DABCO-bromine: An efficient and versatile reagent for bromination of various organic compounds
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Tetrameric DABCO-bromine is a powerful brominating agent but shows reasonable selectivity with certain substrates. The selective bromination for activated aromatic compounds and alkenes is reported. Synthesis of α-bromo ketones and nitriles has also been achieved by using this reagent and the results are also reported. All products reported were obtained in good to excellent yields.
- Heravi, Majid M.,Derikvand, Fatemeh,Ghassemzadeh, Mitra
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p. 125 - 128
(2007/10/03)
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- An intriguing effect of lithium perchlorate dispersed on silica gel in the bromination of aromatic compounds by N-bromosuccinimide
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A convenient and efficient procedure for electrophilic aromatic bromination has been developed by mixing of N-bromosuccinimide and an aromatic compound at room temperature on the surface of silica gel mixed with solid anhydrous LiClO4. All of the substrates examined underwent clean electrophilic aromatic bromination in reaction times of a few minutes to afford the corresponding bromoarenes under neutral conditions in excellent yield. In the case of thiophenol, no substitution reaction occurred, and the corresponding disulfide was obtained in excellent yield.
- Bagheri, Mojtaba,Azizi, Najmedin,Saidi, Mohammad R.
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p. 146 - 149
(2007/10/03)
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- Regioselective and high-yielding bromination of aromatic compounds using hexamethylenetetramine-bromine
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A regioselective and highly efficient method for bromination of aromatic compounds in the presence of a stoichiometric amount of hexamethylenetetramine- bromine (HMTAB) as an efficient reagent in dichloromethane is reported. The selectivity depends on the temperature and nature of the substituent on the substrate. The reactivity of this reagent was increased by supporting it to silica gel for bromination of less activated compounds.
- Heravi, Majid M.,Abdolhosseini, Nafiseh,Oskooie, Hossein A.
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p. 8959 - 8963
(2007/10/03)
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- 2-'5-(5-CARBAMIMIDOYL-1H-HETEROARYL)-6-HYDROXYBIPHENYL-3-YL!- CARBOXYLIC ACID DERIVATIVES AS FACTOR VIIA INHIBITORS
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The present invention relates to novel inhibitors of Factors VIIa, IXa, Xa, XIa, in particular Factor VIIa, pharmaceutical compositions comprising these inhibitors, and methods for using these inhibitors for treating or preventing thromboembolic disorders. Processes for preparing these inhibitors are also disclosed.
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Page/Page column 27
(2010/02/07)
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- Studies on bromination of active methylene by a mixture of hydrobromic acid and hydrogen peroxide (or TBHP)
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Studies on bromination of active methylene with a mixture of hydrogen peroxide or tert-butylhydroperoxide (TBHP) and hydrobromic acid are discussed. Substituted acetophenones, benzocyclic ketones provide α-bromo-keto compounds in high yields under this re
- Tillu, Vasudha H.,Shinde, Popat D.,Bedekar, Ashutosh V.,Wakharkar, Radhika D.
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p. 1399 - 1403
(2007/10/03)
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- Inhibitors of protein kinase for the treatment of disease
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The present invention is directed in part towards methods of modulating the function of protein kinases with phenol- and hydroxynaphthalene-based compounds. The methods incorporate cells that express a protein kinase. In addition, the invention describes methods of preventing and treating protein kinase-related abnormal conditions in organisms with a compound identified by the invention. Furthermore, the invention pertains to phenol- and hydroxynaphthalene-based compounds and pharmaceutical compositions comprising these compounds.
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- Reactions of 3-Isopropenyl- and 3-Acetyltropolone with Quarternary Ammonium Tribromides
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Treatments of 3-isopropenyltropolone with quarternary ammonium tribromides in tetrahydrofuran afforded 3-methyl-8H-cycloheptafuran-8-one.The reactions in methanol-dichloromethane gave 7-bromo-3-methyl-8H-cycloheptafuran-8-one.Bromination of 3-acetyltropolone with the tribromides in tetrahydrofuran produces 3-(bromoacetyl)-tropolone, while the reaction in the methanolic solvent gave 7-bromo- and 5,7-dibromo-substituted 3-acetyltropolones.The brominations of 4'-hydroxyacetophenone were also carried out.
- Matsunaga, Yoichiro,Imafuku, Kimiaki
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p. 295 - 297
(2007/10/02)
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- Optically active liquid crystal compound having cyano group
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An optically liquid crystalline compound having an extremely large spontaneous polarization value and a chiral smectic liquid crystal composition containing the compound are provided, the compound being expressed by the formula STR1 wherein m represents an integer of 2 to 18; l represents an integer of 0 to 12; n represents 0 or 1; R represents an alkyl group or an alkoxy group each of 2 to 20 carbon atoms, a halogen atom or cyano group; and A and B each represent a single bond, STR2 wherein X represents hydrogen atom, a halogen atom or cyano group, and a chiral smectic liquid crystal composition containing at least one kind of the above compound.
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- Synthesis and Structure-Activity Relationships among α-Adrenergic Receptor Agonists of the Phenylethanolamine Type
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Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for α-adrenergic stimulant activity.In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, cyclohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups.The other series is meta hydroxylated with the para position substituted by the same groups.The influence of these groups upon the α-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine,norepinephrine, and norphenylephrine.It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental.The most active compound, α-(aminomethyl)-(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundreth the affinity and the same intrinsic activity as norepinephrine.
- Leclerc, Gerard,Bizec, Jean Claude,Bieth, Nicole,Schwartz, Jean
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p. 738 - 744
(2007/10/02)
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