- Synthesis and crystal structure of 2-benzoyl-4-methyl phenyl benzoate
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The crystal structure of the title compound, C21H 16O3, has been determined. The compound crystallizes in triclinic space group PI with cell parameters a = 9.2240(9) A, b = 9.8050(8) A, c = 10.1610(11) A, α = 94.749(6)°, β = 112.544(4)°, γ = 102.145(6)° and Z = 2. The structure exhibits both intra and intermolecular interactions of the type C-H...O. The intermolecular interaction between the molecules form centrosymmetric dimers.
- Mahendra,Doreswamy,Sridhar,Shashidhara Prasad,Khanum,Shashikanth,Venu
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Read Online
- Series of high spin mononuclear iron(III) complexes with Schiff base ligands derived from 2-hydroxybenzophenones
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The reaction of various phenols with benzoyl chloride afforded the derivatives of phenyl benzoate that subsequently underwent Fries rearrangement. The obtained 2-hydroxybenzophenone analogues were combined with linear aliphatic triamines, which afforded pentadentate Schiff base ligands. Moreover, nine new iron(iii) complexes with the general formula [Fe(Ln)X] (where, Ln is the dianion of the pentadentate Schiff base ligand, N,N′-bis((2-hydroxy-5-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L1, N,N′-bis((2-hydroxy-3,5-dimethylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L2, N,N′-bis((2-hydroxy-5-chlorophenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L3, N,N′-bis((2-hydroxy-4-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L4, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-azaheptane = H2L5, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-methyl-4-azaheptane = H2L6 and X is the chlorido, azido or isocyanato terminal ligand) were synthesized and characterized via elemental analysis, and IR and UV-VIS spectroscopy; in addition, the crystal structures of all the complexes were determined by X-ray diffraction. Magnetic investigation reveals high spin state behaviour in all the reported compounds. DFT calculations and analysis of the magnetic functions allowed to extract absolute values of the zero field splitting parameters and exchange coupling constants.
- Pogány, Luká?,Moncol, Ján,Pavlik, Ján,?alitro?, Ivan
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Read Online
- 2-(2,2-DIARYLETHYL)-CYCLIC AMINE DERIVATIVE OR SALT, SYNTHESIS THEREOF, AND APPLICATION AND COMPOSITION THEREOF
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The disclosure relates to a 2-(2,2-diarylethyl)-cyclic amine derivative or salt, a synthesis method, an application and a composition thereof. Biological activity test shows that this kind of 2-(2,2-diarylethyl)-cyclic amine derivative has good M-receptor antagonistic activity; and can be used as an active component of drugs for the treatment of the diseases mediated or regulated by muscarinic receptors, such as asthma, chronic obstructive pulmonary disease (COPD), overactive bladder (OAB), bronchospasm with chronic obstructive pulmonary disease, visceral spasm, irritable bowel syndrome, Parkinson's disease, depression or anxiety, schizophrenia and related mental diseases.
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Paragraph 0238-0239
(2021/05/28)
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- Water-Tolerant ortho-Acylation of Phenols
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A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.
- Dong, Shuang-Feng,Gao, Zhi-Yuan,He, Yu,Liu, Xu,Loh, Teck-Peng,Tian, Jie-Sheng,Wu, Peng
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supporting information
p. 6594 - 6598
(2021/09/02)
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- Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment?
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In this study, we carried out preparative and mechanistic studies on the photochemical reaction of a series of p-substituted phenyl benzoates in confined and sustainable micellar environment. The aim of this work is mainly focused to show whether the nature of the surfactant (ionic or nonionic) leads to noticeable selectivity in the photoproduct formation and whether the electronic effects of the substituents affect the chemical yields and the rate of formation of the 5-substituted-2-hydroxybenzophenone derivatives. Application of the Hammett linear free energy relationship (LFER) on the rate of formation of benzophenone derivatives, on the lower energy band of the UV-visible absorption spectra of the aryl benzoates and 5-substituted-2-hydroxybenzophenone derivatives allows a satisfactory quantification of the substituent effects. Furthermore, UV-visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the aryl benzoates within the hydrophobic core of the micelle. Finally, TD-DFT calculations have been carried out to estimate the energies of the absorption bands of p-substituted phenyl benzoates and 5-substituted-2-hydroxybenzophenone derivatives providing good linear correlation with those values measured experimentally.
- Siano, Gastón,Crespi, Stefano,Bonesi, Sergio M.
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p. 1298 - 1309
(2021/05/07)
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- Aerobic Copper-Catalyzed Salicylaldehydic Cformyl?H Arylations with Arylboronic Acids
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We report a challenging copper-catalyzed Cformyl?H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl?H bond compared to the phenolic O?H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.
- Xiao, Lin,Lang, Tao-Tao,Jiang, Ying,Zang, Zhong-Lin,Zhou, Cheng-He,Cai, Gui-Xin
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supporting information
p. 3278 - 3283
(2021/02/01)
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- ORGANIC COMPOUNDS
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Disclosed are TRPM8 modulators as defined by formula (I) for achieving a cooling effect on skin and mucousa.
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- Nickel catalyzed intramolecular oxidative coupling: synthesis of 3-aryl benzofurans
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Recent research has been focused on the transition metal-catalyzed reactions. Herein we have developed nickel-catalyzed synthesis of 3-aryl benzofurans fromortho-alkenyl phenolsviaintramolecular dehydrogenative coupling. Notably, simple O2gas served as an oxidant, without using any sacrificial hydrogen acceptor. The strategy enabled the synthesis of 3-aryl benzofurans in good to excellent yields.
- Aggarwal, Sakshi,Satyanarayana, Gedu,Sreenivasulu, Chinnabattigalla,Srinivas, Dasari
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p. 22264 - 22272
(2020/07/03)
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- Nickel-Catalyzed Decarbonyloxidation of 3-Aryl Benzofuran-2(3H)-ones to 2-Hydroxybenzophenones
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We have developed a protocol to facilitate the nickel-catalyzed decarbonyloxidation of 3-aryl benzofuran-2(3H)-ones to 2-hydroxybenzophenones under mild conditions, which is an efficient approach for the decarbonyloxidation of lactones in organic synthesis. A diverse range of substrates can undergo C(O)-O/C(O)-C bond cleavage to generate the target products in good yields. These 2-hydroxybenzophenones can be converted into a variety of compounds via reactions such as esterification, cyclization, and reduction.
- Tong, Zhou,Tang, Zhi,Au, Chak-Tong,Qiu, Renhua
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supporting information
p. 8533 - 8543
(2020/07/16)
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- Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2
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A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.
- Hu, Le' an,Yin, Qin,Zhang, Qing-Wen,Zhang, Xumu,Zhang, Yao
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p. 5321 - 5325
(2020/02/28)
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- Cu/Ag mediated peroxide-free synthesis of benzoylated naphthol derivatives
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A peroxide-free methodology was developed for the synthesis of benzoylated naphthol/phenol derivatives through oxidative deamination reaction performed under aerobic reaction conditions. A synergistic combination of Cu(OTf)2 and Ag2O was used to convert the aminonaphthols and aminophenols to the corresponding benzoylated derivatives. The definite role of atmospheric oxygen to assist the reaction was proved by performing the reaction in the argon atmosphere.
- Prasanna Kumari, Subramaniyan,Suresh, Pavithira,Muthukumar, Vijayashree,Selva Ganesan, Subramaniapillai
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supporting information
(2020/10/13)
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- Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies
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Irradiation of a series of p-substituted aryl benzoates under N2 atmosphere in homogeneous and micellar media was investigated by means of steady-state condition and of time-resolved spectroscopy. A notable selectivity in favor of the 2-hydroxybenzophenone derivatives was observed in micellar media. The benzophenone derivatives were the main photoproduct. On the other hand, in homogeneous media (cyclohexane, acetonitrile, and methanol) the observed product distribution was entirely different, viz. substituted 2-hydroxybenzophenones, p-substituted phenols, benzyl and benzoic acid were found. The binding constants in the surfactant were also measured and NOESY experiments showed that the aryl benzoates were located in the hydrophobic core of the micelle. Laser flash photolysis experiments led to the characterization of both p-substituted phenoxy radical and substituted 2-benzoylcyclohexadienone transients in homogeneous and micellar environment.
- Siano, Gastón,Bonesi, Sergio M.,Crespi, Stefano,Mella, Mariella
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p. 4338 - 4352
(2019/05/01)
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- Asymmetric schiff base metal complex and synthesis method thereof
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The invention relates to the field of synthesis and coordination chemistry, specifically to an asymmetric schiff base (Salen) metal complex. The asymmetric schiff base metal complex is a compound witha structure shown in the attached pictures, wherein M is Zn(II), Ni(II), Cu(II), Co(II), Mn(II) or Fe(III); R1 to R4 are common substituent groups or -H. According to the invention, a series of asymmetric Salen metal complexes are synthesized and are characterized by nuclear magnetic resonance spectrum, elemental analysis, infrared spectroscopy and ultraviolet light visible spectra; the complex is determined to have a selective binding effect on anaxial ligand of imidazole nitrogen-containing small molecules by using an ultraviolet-visible titration method.
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Paragraph 0016; 0018
(2018/11/22)
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- Diaryl vinyl cyclic amine derivatives and preparation method thereof
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The invention provides diaryl vinyl cyclic amine derivatives and a preparation method thereof. The aryl substituted groups of the diaryl vinyl cyclic amine derivatives have a hydroxyl or hydroxy derivative functional groups in the ortho positions of vinyl groups. The bioactivity test shows that the compounds have anticholinergic activity, and the ortho-hydroxy groups can significantly enhance theantagonistic activity; the compounds can be used as active pharmaceutical ingredients for treating asthma, chronic obstructive pulmonary disease (COPD), rhinorrhea caused by allergic rhinitis and cold, urinary incontinence, Parkinson's disease, and the like.
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Paragraph 0144; 0145; 0190; 0192-0195
(2018/09/08)
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- Practical and efficient synthesis of hydroxyaryl ketones catalyzed by HF@SiO2 under solvent-free condition
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A wide variety of hydroxyaryl ketones bearing different motifs was successfully synthesized with good yields and excellent selectivities in the presence of HF@SiO2 as an environmental friendly acid under solvent-free condition. Mild and green reaction conditions and excellent yields (50-91%) make this method an attractive method for the efficient synthesis of hydroxyaryl ketones. Fries rearrangement of phenyl benzoate in the presence of HF@SiO2 led to p-hydroxybenzophenone, while phenyl acetate in the same conditions produced o-hydroxyacetophenone as a single isomer.
- Paghandeh, Hossein,Saeidian, Hamid,Ghaffarzadeh, Mohammad
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p. 809 - 814
(2018/09/26)
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- Synthetic method of benzophenone type compound catalyzed by boron trifluoride
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The invention provides a synthetic method of benzophenone type compound catalyzed by boron trifluoride. The method comprises the following specific steps: adding substituted benzoic acid, a resorcinolderivative and a catalyst boron trifluoride diethyl etherate to a reaction vessel, gradually raising the temperature to 95-120 DEG C, performing reaction for 10-30 min, then performing dissolution with ethyl acetate, performing washing with an equal amount of saturated sodium bicarbonate, and performing drying, recrystallization and decolorization to obtain the benzophenone type compound. The technical scheme provided by the invention has the advantages that the operation is simple and convenient; the substituted benzoic acid and the resorcinol derivative are taken as raw materials to synthesize the benzophenone type compound in one step, thereby reducing the production cost; reaction conditions are mild; the by-product is water which is friendly to the environment; the atom utilization ratio is high; the reaction post-treatment is simple; and the yield can reach 90% or above.
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Paragraph 0030; 0034
(2018/10/19)
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- Acid-Functionalised Magnetic Ionic Liquid [AcMIm]FeCl4 as Catalyst for Oxidative Hydroxylation of Arylboronic Acids and Regioselective Friedel–Crafts Acylation
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An acid-functionalised, magnetic, room-temperature ionic liquid, 1-acyl-3-methylimidazolium tetrachloroferrate ([AcMIm]FeCl4), was synthesised and its optical, magnetic, and thermal properties were investigated. The magnetic moment (0.05402 emu in 2 T magnetic fields) showed strong paramagnetic behaviour, and thermogravimetric analysis indicated very good thermal stability with a decomposition temperature higher than 230 °C. Additionally, [AcMIm]FeCl4 efficiently catalysed the oxidative ipso-hydroxylation of arylboronic acids and regioselective Friedel–Crafts acylation without external organic solvent or additives, such as acids, base, and ligands. This functionalised ionic liquid, [AcMIm]FeCl4, was recycled and reused at least six times without significant loss of its catalytic properties and stability.
- Saha, Arijit,Payra, Soumen,Dutta, Dipa,Banerjee, Subhash
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p. 1129 - 1134
(2017/08/18)
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- Efficient microwave-assisted direct C-benzoylation of phenols and naphthols with benzoic acid catalyzed by bismuth triflate under solvent-free or ionic liquid conditions
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An efficient and simple route for the synthesis of ortho-hydroxyaryl ketones has been developed. The microwave-assisted direct C-benzoylation of phenols and naphthols in the presence of metal triflates afforded the corresponding ortho-hydroxyaryl ketones in moderate to excellent yields. Bismuth triflate showed the best catalytic performance compared to other metal triflates. The protocol has advantages including short reaction times, high chemoselectivity towards C-acylation, and simple work-up. Additionally, bismuth triflate can be easily recovered and reused several times without significant loss of catalytic performance.
- Tran, Phuong Hoang,Phung, Huy Quang,Duong, Minh Nhat,Pham-Tran, Nguyen-Nguyen
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supporting information
p. 1558 - 1563
(2017/04/03)
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- Acylation of Csp2-H bond with acyl sources derived from alkynes: Rh-Cu bimetallic catalyzed CC bond cleavage
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A Rh-Cu bimetallic catalyzed o-acylation of acyloxacetamide with alkynes has been described. This transformation provides a novel, concise way to synthesize ortho-acylphenols using functionalized alkynes as acylating reagents. Mechanistic studies revealed a Rh-Cu relay process, in which O2 plays a critical role for the formation of carbonyl compounds.
- Xie, Ying
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p. 12372 - 12375
(2016/10/22)
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- Copper catalyzed oxidative deamination of Betti bases: An efficient approach for benzoylation/formylation of naphthols and phenols
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An efficient route for benzoylation or formylation of naphthols/phenols is developed via oxidative deamination of Betti bases. A copper salt catalyst with TBHP as an oxidant is used. Water is used as a reagent as well as solvent. The reaction proceeds through a regioselective radical pathway. Most importantly, the position of acylation is unambiguous. The method is also applicable to non-hydroxy substrates.
- Deb, Mohit L.,Pegu, Choitanya Dev,Borpatra, Paran J.,Baruah, Pranjal K.
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p. 40552 - 40559
(2016/05/24)
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- Chemoselective C-benzoylation of phenols by using ALCl3under solvent-free conditions
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Substituted phenols were chemo-selectively reacted with benzoylchloride in presence of aluminum chloride under solvent-free condition to afford the corresponding 2′-hydroxy aryl benzophenones in excellent yields (72-96%). Naphthol benzoylation resulted in lower yields as compared to phenols. Both reactions completed in 5-10 min with quantitative yields providing excellent control over regioselectivity of products.
- Gaikwad, Sunil V.,Nawghare, Beena R.,Lokhande, Pradeep D.
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p. 319 - 325
(2015/07/27)
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- Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids
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A Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids has been developed, with features of mild reaction condition and high efficiency. Furthermore, the functionalized 2-hydroxybenzophenone could be subject to divergent synthesis of heterocycles.
- Wang, Dahai,Cui, Sunliang
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p. 8511 - 8516
(2016/01/25)
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- Catalytic application of fluorous silica gel in Fries rearrangement
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Commercially available fluorous silica gel (Fluoro Flash) with no further post-modification was successfully investigated and applied merely as a catalyst in Fries rearrangement of various aryl esters under solvent free conditions in 4 h and optimized temperatures. In addition to good yields and recyclability of the catalyst, toxicity of reaction medium, by-products, and wastes were minimized. Also, low catalyst loading was another advantage of this methodology.
- Ghaffarzadeh, Mohammad,Ahmadi, Maryam
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- One-pot synthesis of 3,4-disubstituted coumarins under catalysis of Mn 3O4 nanoparticles
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The one-pot synthesis of 3,4-disubstituted coumarins from substituted 2-(hydroxymethyl)phenols with β-keto esters catalyzed by Mn 3O4 nanoparticles was developed. A series of 3,4-disubstituted coumarin derivatives were obtained in good yields. A new method for the one-pot synthesis of 3,4-disubstituted coumarins from substituted 2-(hydroxymethyl)phenols with β-keto esters catalyzed by Mn 3O4 nanoparticles has been developed. A series of 3,4-disubstituted coumarin derivatives were synthesized from substituted 2-(hydroxymethyl)phenols and β-keto esters in good yields. Copyright
- Sun, Huayin,Zhang, Yonghui,Guo, Fengfeng,Yan, Yizhe,Wan, Changfeng,Zha, Zhenggen,Wang, Zhiyong
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p. 480 - 483
(2012/03/09)
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- Catalyst Compounds and Use Thereof
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This invention relates to Group 4 catalyst compounds containing di-anionic tridentate nitrogen/oxygen based ligands. The catalyst compounds are useful, with or without activators, to polymerize olefins, particularly a-olefins, or other unsaturated monomers. Systems and processes to oligomerize and/or polymerize one or more unsaturated monomers using the catalyst compound, as well as the oligomers and/or polymers produced therefrom are also provided.
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- A facile synthesis of highly functionalized 4-arylcoumarins via kostanecki reactions mediated by DBU
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An efficient synthesis of 4-arylcoumarins has been accomplished via Kostanecki reactions of 2-hydroxybenzophenones with acetic anhydride employing DBU at ambient temperature. Using the same strategy, several 2-acyloxybenzophenone derivatives were readily converted to 3,4-difunctionalized coumarins. This protocol offers a notable improvement in reaction conditions for coumarin synthesis and takes advantage of its synthetic capability, especially for highly functionalized 4-arylcoumarins with structural diversity.
- Hwang, In-Taek,Lee, Sun-Ah,Hwang, Jin-Soo,Lee, Kee-In
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body text
p. 6313 - 6321
(2011/10/11)
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- A facile demethylation of ortho substituted aryl methyl ethers promoted by AlCl3
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An efficient and practical demethylation of ortho substituted aryl methyl ethers using AlCl3 has been developed. This method gives a high conversion, is simple to operate and is cost-effective. A mechanism involving the complexation of AlCl3 with the OMe and the adjacent electron withdrawing group is proposed. Many functional groups can be tolerated in the demethylation process, and 29 examples gave a demethylated product in a yield of 90-98%.
- Du, Zhen-Ting,Lu, Jing,Yu, Hong-Rui,Xu, Yan,Li, An-Pai
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experimental part
p. 222 - 227
(2010/08/04)
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- A comparative study: One pot synthesis of some prochiral ketones using conventional and microwave assisted methods
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Polyphosphoric acid (PPA) has been used to synthesize a number of prochiral aryl ketones as well as α,β-unsaturated diaryl ketones by conventional and microwave assisted methods in moderate to good yield. The microwave assisted method is advantageous due to increased yield and high purity of products within incredible short period of time.
- Salokhe,Mote,Suryavanshi,Salunkhe
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experimental part
p. 1347 - 1351
(2010/07/05)
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- Regioselective synthesis of 5-alkylsalicylates, 5-alkyl-2-hydroxy- acetophenones, and 5-alkyl-2-hydroxy-benzophenones by [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 2-alkyl-1,1,3,3-tetraethoxypropanes
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(Chemical Equation Presented) A variety of 5-alkylsalicylates, 5-alkyl-2-hydroxy-acetophenones, and 5-alkyl-2-hydroxy-benzophenones was regioselectively prepared by TiCl4 mediated formal [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 2-alkyl-1,1,3,3- tetraethoxypropanes.
- Mamat, Constantin,Buettner, Stefan,Trabhardt, Tiana,Fischer, Christine,Langer, Peter
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p. 6273 - 6275
(2008/02/10)
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- Synthesis and crystallographic analysis of benzophenone derivatives-The potential anti-inflammatory agents
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Fries rearrangement of substituted phenyl benzoates 1a-j to substituted hydroxy benzophenones 2a-j was achieved in excellent yield. Further benzoylation of 2a-j to benzoyloxy benzophenones 4a-n, a benzophenone analogue was achieved in good yield. All the newly synthesized compounds were evaluated for their anti-inflammatory activity and were compared with standard drugs. Out of the compounds studied, the compounds 4c, 4e, 4g, 4h and 4k with chloro and methyl substituents at para position showed more potent activity than the standard drugs at all doses tested.
- Venu,Shashikanth,Khanum,Naveen,Firdouse, Aiysha,Sridhar,Shashidhara Prasad
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p. 3505 - 3514
(2008/02/07)
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- Direct acylation of phenol and naphthol derivatives in a mixture of graphite and methanesulfonic acid
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Graphite in methanesulfonic acid is used to prepare o-hydroxyketones by direct acylation of phenol and naphthol derivatives with carboxylic acids. Georg Thieme Verlag Stuttgart.
- Sharghi, Hashem,Hosseini-Sarvari, Mona,Eskandari, Razieh
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p. 2047 - 2052
(2007/10/03)
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- Synthesis of aryl ketones or ketimines by palladium-catalyzed arene C-H addition to nitriles
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The unprecedented palladium-catalyzed C-H addition of arenes to nitriles provides moderate to excellent yields of aryl ketones or the corresponding hindered imines. The addition of a small amount of DMSO increases the yields dramatically. Both intermolecular and intramolecular reactions are successful, although the intramolecular reactions tend to be more sluggish. This novel chemistry is believed to involve palladium-catalyzed C-H activation of the arene by electrophilic aromatic substitution, followed by the unusual carbopalladation of a nitrile. Similar reactions have been successfully developed employing arylboronic acids and nitriles. A concise route to xanthones starting from cheap starting materials has been developed employing this synthetic protocol.
- Zhou, Chengxiang,Larock, Richard C.
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p. 3551 - 3558
(2007/10/03)
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- Microwave assisted direct ortho-acylation of phenol and naphthol derivatives by BF3·(C2H5)2O
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The solventless acylation of phenol and naphthol derivatives with various organic acids and BF3·(C2H5) 2O, under microwave conditions, was studied. High yields of the o-acylated products were achieved in a very short time.
- Naeimi, Hossein,Moradi, Leila
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p. 284 - 287
(2008/02/04)
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- Synthesis of benzoyl phenyl benzoates as effective inhibitors for phospholipase A2 and hyaluronidase enzymes
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Benzoylation of (hydroxy phenyl) phenyl methanone 2a-g to benzoyl phenyl benzoates 4a-g, a benzophenone analogue, was achieved in good yield. All the newly synthesized compounds were evaluated for their phospholipase A2 [E.C. 3.1.1.4] and hyaluronidase [E.C. 3.2.1.35] enzyme inhibitory activity in snake venom as source and their structure-activity relationship with respect to different groups is reported for the first time. The in vitro PLA2 enzyme inhibitory activity and in vivo anti-inflammatory activity studies of benzoyl phenyl benzoates are illustrated.
- Khanum, Shaukath Ara,Murari, Satish Kumar,Vishwanth, Bannikuppe Sannanaik,Shashikanth, Sheena
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p. 4100 - 4104
(2007/10/03)
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- Improvement of Selectivity in the Fries Rearrangement and Direct Acylation Reactions by Means of P2O5/SiO2 Under Microwave Irradiation in Solvent-Free Media
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P2O5/SiO2 was found to be an efficient new reagent for the Fries rearrangement of acyloxy benzene or naphthalene derivatives and the direct acylation reactions of phenol and naphthol derivatives with carboxylic acids. The reactions proceeded smoothly in the solid state and are highly selective methods for the preparation of the ortho isomers of hydroxyaryl ketones. Microwave irradiation improved the conversion yield to 85-100 percent and the high ortho-regioselectivity of these reactions provides an efficient and versatile procedure for obtaining o-hydroxyaryl ketones in 47-98 percent yield.
- Eshghi, Hossein,Rafie, Mohammad,Gordi, Zinat,Bohloli, Moosa
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p. 1258 - 1270
(2007/10/03)
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- Identification of ligand-binding regions of P-glycoprotein by activated-pharmacophore photoaffinity labeling and matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry
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Energy dependent efflux pumps confer resistance to anticancer, antimicrobial, and antiparasitic drugs. P-glycoprotein (Pgp, ABCB1) mediates resistance to a broad spectrum of antitumor drugs. Compounds that themselves are nontoxic to cells have been shown to act as inhibitors of Pgp. The mechanism of binding and transport of low-molecular-mass ligands by Pgp is still incompletely understood. This study introduces a series of propafenone-related photoaffinity ligands, which combine high specificity and selectivity for Pgp with high labeling efficiency. Molecules are intrinsically photoactivatable in the arylcarbonyl group, which represents a pharmacophoric substructure for this group of ligand molecules. A detailed study of the structure-activity relationship for this type of photoligand is presented. In subsequent experiments, these ligands were used to characterize the drug-binding domain of propafenone-type analogs. Matrix-assisted laser desorption/ionization - time-of-flight (MALDI-TOF) mass spectrometry shows that propafenone-type ligands preferentially label fragments assigned to putative transmembrane segments 3, 5, 6, 8, 10, 11, and 12. Labeled fragments are also identified in a highly charged region of 15 amino acids in the second cytoplasmic loop. This region corresponds to the so-called EAA-like motif, which has been proposed to play a role in the interaction between transmembrane domain and nucleotide binding domain of peroxisomal ATP-binding cassette transporters. In addition, a region in cytoplasmic loop 3 and between TM12 and the N terminus of the Walker A sequence of NBD2 are labeled by the ligands. Therefore, a number of confined protein regions contribute to the drug-binding domain of propafenone-type analogs.
- Ecker, Gerhard F.,Csaszar, Edina,Kopp, Stephan,Plagens, Brigitte,Holzer, Wolfgang,Ernst, Wolfgang,Chiba, Peter
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p. 637 - 648
(2007/10/03)
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- Preparation of hydroxybenzophenones using silica-gel supported ferric chloride
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The synthesis of commercially important hydroxybenzophenones by condensing phenols with benzotrichloride has been reported. Benzoylation is catalyzed by silica supported ferric chloride under solvent-free conditions. Hydroxybenzophenones are isolated in low to moderate yields.
- Bendale, Pravin M.,Khadilkar, Bhushan M.
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p. 1738 - 1739
(2007/10/03)
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- Fries rearrangement in ionic melts
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1-Butyl-3-methylimidazolium chloroaluminate, [BMIm]+Al2Cl7-, was used as a solvent as well as a Lewis acid catalyst in Fries rearrangement reactions of phenyl benzoates. The rate of consumption of phenyl benzoate obeyed first-order kinetics. Good yields and high selectivity are the features observed in this unconventional but interesting aprotic solvent.
- Harjani, Jitendra R.,Nara, Susheel J.,Salunkhe, Manikrao M.
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p. 1979 - 1981
(2007/10/03)
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- Hypervalent iodine in synthesis XXXIV: Palladium-catalyzed coupling reaction of o-hydroxyarylaldehydes with hypervalent iodonium salts via cleavage of the aldehyde C-H bond
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A novel way of preparation for o-hydroxyarylketones with mild conditions and good yields by palladium-catalyzed coupling reaction of o- hydroxyarylaldehydes with hypervalent iodonium salts via the cleavage of the aldehyde C-H bond has been reported.
- Xia, Min,Chen, ZhenChu
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p. 531 - 536
(2007/10/03)
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- Hypervalent iodine in synthesis 59: Application of polymeric diaryliodonium salts as aryl transfer reagents in SPOS
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Polymeric diaryliodonium salts were employed as aryl transfer reagents in the Pd(II) catalyzed cross-coupling reaction with salicylaldehydes, and could be regenerated and recycled for the same reactions.
- Chen,Chen
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p. 1175 - 1177
(2007/10/03)
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- Tandem Fries Reaction-Conjugate Addition under Microwave Irradiation in Dry Media; One-pot Synthesis of Flavanones
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An AlCl3-ZnCl2 mixture supported on silica gel is found to be an efficient medium for the Fries rearrangement of acyloxybenzene or naphthalene derivatives in solvent-free conditions under microwave irradiation.
- Moghaddam, Firouz Matloubi,Ghaffarzadeh, Mohammad,Abdi-Oskoui, Seyed Hossein
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p. 574 - 575
(2007/10/03)
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- Alumina in Methanesulfonic Acid (AMA) as a New Efficient Reagent for Direct Acylation of Phenol Derivatives and Fries Rearrangement. A Convenient Synthesis of o-Hydroxyarylketones
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Alumina in methanesulfonic acid (AMA) is used to prepare o-hydroxyaryl ketones by acylation of phenol and naphthol derivatives with carboxylic acids and the Fries rearrangement of phenolic esters. Mechanistic studies show that the acylation reaction in AMA occurred through an esterification followed by a Fries rearrangement of the phenolic ester by an intermolecular mechanism.
- Sharghi, Hashem,Kaboudin, Babak
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p. 2678 - 2695
(2007/10/03)
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- A novel and facile synthesis of 1,2,3-triacylbenzenes
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3,4,5-Triacyltoluenes 7 were prepared in high yield by a novel oxidative cleavage reaction of 2,6-diacylcresol monohydrazone 6 with lead tetraacetate.
- Kotali,Glaveri,Pavlidou,Tsoungas
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p. 1172 - 1173
(2007/10/02)
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- THE 2-(TRIMETHYLSILYL)ETHOXYMETHOXY (OSEM) DIRECTED ORTHO METALATION GROUP. NEW REGIOSPECIFIC SYNTHETIC ROUTES TO SUBSTITUTED BENZENES AND PYRIDINES
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Regiospecific routes to ortho-substituted phenols and 3-pyridinols have been developed using the OSEM Directed Metalation Group.
- Sengupta, Saumitra,Snieckus, Victor
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p. 4267 - 4270
(2007/10/02)
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- Reactions of 4-Benzoyl-4-methylcyclohexa-2,5-dienone in Acids: Retro-Fries Rearrangements
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4-Benzoyl-4-methylcyclohexa-2,5-dienone is known as one of the few relatively stable 4-acylcyclohexa-2,5-dienones.In attempts to achieve dienone-phenol rearrangements with acyl migration it has been treated with Lewis acids and with non-nucleophilic acids in non-polar solvents.In each case rapid acil migration occurs to give 4-methylphenyl benzoate by a retro-Fries rearrangement, along with some cleavage to the phenol.The benzoyl group can be trapped by another phenol, and the mechanism is formulated as a dissociation-recombination process with significant leakage of the 4-methylphenol and benzoyl cation.The reaction is compared with the Fries/retro-Fries equilibrium which has been induced between phenyl esters and 2- and 4-acyl phenols.Observations are made on the photochemical Fries rearrangement of 4-methylphenyl acetate, which has been suggested to proceed via 4-acetyl-4-methylcyclohexa-2,5-dienone, and of 4-methylphenyl benzoate.
- Jackson, Lorraine B.,Waring, Anthony J.
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p. 1893 - 1898
(2007/10/02)
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- Cyclodeshydratation d'aryloxy-2 diaryl-1,2 ethanones en diaryl-2,3 benzofurannes. Influence de la substitution sur la competition entre deux chemins reactionnels
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Many of the methods for synthesizing derivatives of 2,3-diaryl benzofurans imply cyclodehydration of 1,2-diaryl 2-aryloxyethanones, leading often to a mixture of two isomers which differ by the presence of the aryl substituent at positions C-2 or C-3 of benzofuran.This isomerisation is explained by a competition between two possible mechanisms.Either a direct electrophilic substitution or the intermediate formation of an α-acylcarbenium ion.This study deals with the competition as determined by the substitution of aryl groups in the initial substrate.Each 2,3-diarylbenzofuran was synthesized previously using an unambiguous method.
- Montfort, Bernard,Laude, Bernard,Vebrel, Joel,Cerutti, Ernest
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p. 848 - 854
(2007/10/02)
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- PHOTOREARRANGEMENT OF ARYL ESTERS IN MICELLAR MEDIUM
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Effect of micelle (SDS ) on the photorearrangement of aryl esters have been investigated.Thus, phenyl, p- and m-cresyl, and 2-naphthyl benzoates yielded the corresponding o-hydroxybenzophenones as a major product in high yield.Phenyl cinnamate gave 2-hydroxychalcone. 2,4,6-Tri-t-butyl-phenylbenzoate, however, underwent decarboxylation yielding 2,4,6-tri-t-butyl biphenyl in quantitative yield.
- Singh, Anil K.,Sonar, Sanjay M.
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p. 1113 - 1122
(2007/10/02)
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- Carbanionically Induced -Migrations of ?- and Coordinatively Unsaturated Groups
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According to a general reaction scheme, o-lithioaryl esters 4a,b, amides 13a,b 17b, and amidines 39b of non-enolizable carboxylic acids as well as a corresponding diphenylphosphinic amide 51b react under mild conditions to give the intensely coloured lithium derivatives of o-acylphenoles 6a,b and o-acylarenamines 15a,b, 18a, 41a, 52a, which are finally hydrolyzed to the neutral products 7a,b, 14a,b, 18b, 41b, 52b, respectively.The lithiated precursors of the rearrangement are mostly prepared by halogen/metal exchange reactions.In the case of N,N-di-p-tolylpivalamide 33 such a -rearrangement also could be induced by direct metalation of the educt.With N-methyl-N-phenylpivalamide (29), however, exclusive metalation of the N-methyl group occurs, followed by -migration of the pivaloyl group.Silyl groups, too, can undergo analogous -shifts, as was demonstrated by the rearrangement of the o-lithiated N-(trimethylsilyl)aniline 63b to the o-(trimethylsilyl)anilines 65a,b.When a benzoyl and sulfonyl group can compete for the -shifts, as in the N-tosylated benzamide 47b, only the benzoyl group migrates.However, the migration tendency of the trimethylsilyl group equals that of the benzoyl group as was shown with the N-silylated benzamide 66b.
- Hellwinkel, Dieter,Laemmerzahl, Frank,Hofmann, Gunter
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p. 3375 - 3405
(2007/10/02)
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