- Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts
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A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.
- Bouquin, Maxime,Jaroschik, Florian,Taillefer, Marc
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- Mn/Cu catalyzed addition of arylboronic acid to nitriles: Direct synthesis of arylketones
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A direct and efficient synthesis of arylketones via arylboronic acid addition to nitriles in presence of inexpensive Mn/Cu catalytic system is reported. The use of non-precious Mn and Cu salts has been found to be highly advantageous both in terms of accessibility as well as cost effectiveness. A series of arylboronic acids as well as nitriles were used to synthesize a variety of symmetrical and unsymmetrical arylketones. Based on the literature studies, the reaction mechanism is anticipated to go through an aryl radical intermediate which reacted with the copper activated nitrile to give the desired arylketones after the hydrolysis of the imine intermediate.
- Moustafa, Dina,Sweet, Chelsea,Lim, Hyun,Calalpa, Brenda,Kaur, Parminder
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p. 3816 - 3820
(2018/09/18)
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- PtO2/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups
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A highly efficient PtO2/PTSA catalyst system for the hydration of a wide array of alkynes was developed. This method proved to be compatible with a large range of functional groups and the ketone products were obtained in high yields. The scope of this methodology was also extended to the synthesis of 3-Aryl-isochromenones,-indoles and-benzofurans.
- Lin, Hsin-Ping,Ibrahim, Nada,Provot, Olivier,Alami, Mouad,Hamze, Abdallah
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p. 11536 - 11542
(2018/04/05)
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- A general synthesis of ynones from aldehydes via oxidative C-C bond cleavage under aerobic conditions
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We describe a direct synthesis of various ynones from readily available aldehydes and hypervalent alkynyl iodides. In this method, a gold catalyst and a secondary amine work synergistically to produce the trisubstituted allenyl aldehyde, which can be conv
- Wang, Zhaofeng,Li, Li,Huang, Yong
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p. 12233 - 12236
(2014/10/15)
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- Design, synthesis, and cytotoxic activities of new 2,4,5-triarylimidazoles
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A new group of 2,4,5-triarylimidazoles containing N,N-dimethylaminoethoxy or piperidinyl ethoxy group at the para position of the C-5 phenyl ring were synthesized and their cytotoxic activities were evaluated on three different breast cancer cell lines using MTT assay. The compounds contain various substituents at the para position of C-2 phenyl ring. Among the synthesized compounds, 4-(5-(4-(2-piperidin-1-yl)ethoxy)phenyl)-4-phenyl-1H-imidazol-2-yl) phenol (11e) and 1-2-(4-(2,4-diphenyl-1H-imidazol-5-yl)phenoxy)ethyl) piperidine (11h) with IC50s of less than 0.1 μM on all three cell lines were the most potent cytotoxic compounds.
- Zarghi,Arfaei,Shirazi
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p. 3897 - 3904
(2013/07/26)
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- Diarylated ethanones from Mo(CO)6-mediated and microwave-assisted palladium-catalysed carbonylative Negishi cross-couplings
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Two protocols for palladium-catalysed carbonylative Negishi cross-couplings were developed for aryl iodides and aryl bromides. The two main breakthroughs were that molybdenum hexacarbonyl [Mo(CO)6] could be used as a solid in situ source of CO, and that controlled microwave irraditaion could be used for heating. Consequently, the reactions were safe (in contrast to when CO gas was used) and fast (in comparison to when conventional heating was used). The carbonylative cross-coupling reactions were carried out using commercially available benzylzinc bromide in closed vials (90-120°C for 0.5-1 h) to give a set of diarylated ethanones, a common pharmacophore found in several pharmaceuticals, in moderate to high isolated yields (47-84 %). The mild three-component carbonylation protocol presented here is operationally simple, safe, and rapid, and the formation of the carbonylative Negishi cross-coupling product is favoured over the product of Negishi cross-coupling. Copyright
- Motwani, Hitesh V.,Larhed, Mats
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supporting information
p. 4729 - 4733
(2013/08/23)
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- Triphenylalkene derivatives and their use as selective estrogen receptor modulators
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The invention provides novel selective estrogen receptor modulator compounds of the general formula: wherein R1 and R2, which are the same or different are a) H, halogen, OCH3, OH; or ?where X is O, NH or S; and n is an integer from 1 to 4; and R4 and R5, which are the same or different, are a 1 to 4 carbon alkyl, H, —CH2C≡CH or —CH2CH2OH; or R4 and R5 form an N-containing five- or six-membered ring or heteroaromatic ring; or c) —Y—(CH2)nCH2—O—R6 where Y is O, NH or S and n is an integer from 1 to 4; and R6 is H, —CH2CH2OH, or —CH2CH2Cl; or d) 2,3-dihydroxypropoxy, 2-methylsulfamylethoxy, 2-chloroethoxy, 1-ethyl-2-hydroxyethoxy, 2,2-diethyl-2-hydroxyethoxy or carboxymethoxy; and R3 is H, halogen, OH or —OCH3; stereoisomers thereof and their non-toxic pharmaceutically acceptable salts and esters and mixtures thereof, which compounds exhibit valuable pharmacological properties.
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- A convenient one-pot completely stereoselective synthesis of trans-4-Hydroxystilbenes and its derivatives and X-ray structure of its precursor
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The synthesis of E-isomer of 4-Hydroxystilbene and its derivatives 3 by reductive elimination of the carbonyl function in 2-phenyl-1-(4-hydroxyphenyl)ethan-1-one and its derivatives 2 and the X-ray structure of 2a are described.
- Chhor, Rakeshwar B.,Singh, Kunwar A.,Nosse,Tandon, Vishnu K.
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p. 2519 - 2530
(2007/10/03)
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- Nickel catalysed electrosynthesis of ketones from organic halides and iron pentacarbonyl. Part 2: Unsymmetrical ketones
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Unsymmetrical aryl-benzyl or aryl-alkyl ketones are obtained by electrolysing in an undivided cell a DMF solution containing two organic halides, iron pentacarbonyl and a catalytic amount of a nickel-2,2′-bipyridine complex.
- Dolhem, Eric,Barhdadi, Rachid,Folest, Jean Claude,Nédelec, Jean Yves,Troupel, Michel
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p. 525 - 529
(2007/10/03)
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- Photo-fries rearrangements of phenyl phenylacylates in polyethylene films. Comparison of reactivity and selectivity with 1-naphthyl phenylacylates
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The fates and kinetics of recombination of singlet radical pairs generated by photolyses of three phenyl phenylacylates have been examined in unstretched and stretched polyethylene films. Comparisons with results from photolyses of analogous 1-naphthyl phenylacylates in the same media lead to the conclusions that (1) phenoxy is less reactive overall than 1-naphthoxy toward a common phenylacyl radical but (2) the constrained cages in which the radical pairs reside exert greater control over the movements of the 1-naphthoxy/phenylacyl pairs. The reasons for these observations are discussed in the context of the shapes and van der Waals volumes of the radical pairs, the void volumes of sites in native polyethylene films, and the electronic properties of the aryloxy radicals. The fates and kinetics of recombination of singlet radical pairs generated by photolyses of three phenyl phenylacylates have been examined in unstretched and stretched polyethylene films. Comparisons with results from photolyses of analogous 1-naphthyl phenylacylates in the same media lead to the conclusions that (1) phenoxy is less reactive overall than 1-naphthoxy toward a common phenylacyl radical but (2) the constrained cages in which the radical pairs reside exert greater control over the movements of the 1-naphthoxy/phenylacyl pairs. The reasons for these observations are discussed in the context of the shapes and van der Waals volumes of the radical pairs, the void volumes of sites in native polyethylene films, and the electronic properties of the aryloxy radicals.
- Gu,Weiss
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p. 1775 - 1780
(2007/10/03)
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- Novel inhibitors of the enzyme estrone sulfatase (ES)
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We report the initial results of our study into a series of simple 4-sulfamated phenyl alkyl ketones as potential inhibitors of the enzyme estrone sulfatase. The results of the study show that these compounds are potent inhibitors, possessing greater inhibitory activity than COUMATE, but weaker activity than EMATE. Furthermore, the compounds are observed to be irreversible inhibitors.
- Ahmed, Sabbir,James, Karen,Owen, Caroline P,Patel, Chirag K,Patel, Mijal
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p. 841 - 844
(2007/10/03)
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- Hydrophobicity, a physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES)
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We report the initial structure-activity relationship study (SAR) (in particular log P) of a series of compounds based upon 4-sulfamated phenyl ketones as potent inhibitors of the enzyme estrone sulfatase (ES). The results of the study show that these compounds are irreversible inhibitors of ES and that they are more potent than COUMATE, but weaker than EMATE. Analysis of the SAR data shows a strong correlation between IC50 and log P but also supports our previous study, which suggests a very strong relationship between pKa and IC50.
- Ahmed, Sabbir,James, Karen,Owen, Caroline P.,Patel, Chirag K.,Patel, Mijal
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p. 2525 - 2528
(2007/10/03)
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- Selectivity in the photo-Fries reaction of phenyl phenylacetates included in a nation membrane
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Photoirradiation of phenyl phenylacetates included within a Nafion membrane exclusively resulted in ortho-hydroxyphenones, thus achieving high selectivity in the photo-Fries reaction.
- Tung, Chen-Ho,Xu, Xiao-He
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p. 127 - 130
(2007/10/03)
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- Photochemistry of phenyl phenylacetates adsorbed on pentasil and faujasite zeolites
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The photochemistry of phenyl phenylacetate 1, p-tolyl phenylacetate 2, o-tolyl phenylacetate 3 and phenyl o-tolylacetate 4 was investigated both in homogeneous solution and adsorbed on ZSM-5 and NaY zeolites.Photolyses of these esters in acetonitrile result in photo-Fries rearrangement products, phenols and diphenylethane as well as phenyl benzyl ethers.In contrast, photolyses of these esters adsorbed on NaY zeolite only give the ortho Fries rearrangemnt products.On the other hand, the photochemical reaction of 1 and 2 adsorbed on ZSM-5 zeolite only produces toluene and phenols, while under identical conditions the photochemical products for 3 and 4 are the Fries rearrangement and decarbonylation products. the product distributions for these esters adsorbed both on ZSM-5 and NaY zeolites are different from those for dibenzyl ketones as reported in the literature.All of these observations are interpreted in terms of (a) the size and shape sorption selectivity of ZSM-5 zeolite, (b) restriction of duffusional and rotational mobility of the radical pair imposed by the zeolite surface and (c) the multiplicity of the excited state responsible for the homolytic bond cleavage.
- Tung, Chen-Ho,Ying, Yun-Ming
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p. 1319 - 1322
(2007/10/03)
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- Non-peptidic inhibitors of human neutrophil elastase: The design and synthesis of sulfonanilide-containing inhibitors
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A novel series of pivaloyloxy benzene derivatives has been identified as potent and selective human neutrophil elastase (HNE) inhibitors. Convergent syntheses were developed in order to identify the inhibitors which are intravenously effective in an animal model. A compound of particular interest is the sulfonanilide-containing analogues. Structure-activity relationships are discussed. Structural requirements for metabolic stabilization are also discussed.
- Imaki, Katsuhiro,Okada, Takanori,Nakayama, Yoshisuke,Nagao, Yuuki,Kobayashi, Kaoru,Sakai, Yasuhiro,Mohri, Tetsuya,Amino, Takaaki,Nakai, Hisao,Kawamura, Masanori
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p. 2115 - 2134
(2007/10/03)
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- Synthesis of deoxybenzoins
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Zinc chloride-phosphoryl chloride is an efficient condensing agent for the preparation of hydroxy(methoxy)deoxybenzoins at room temperature directly from phenols and arylacetic acids.
- Devi, Nirada,Jain, Niveta,Krishnamurty, H. G.
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p. 874 - 875
(2007/10/02)
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- Expedient Synthesis of Polyhydroxyisoflavones
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A general and direct synthesis of polyhydroxy isoflavones (3-phenyl-4H-1-benzopyran-4-ones) starting from the corresponding unprotected phenols and arylacetic acids is described.The aryl rings may carry additional alkyl, methoxy and/or halogeno groups.Intermediate polyhydroxydeoxybenzoins (1,2-diphenylethanones) can also be isolated in good yields.
- Waehaelae, Kristiina,Hase, Tapio A.
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p. 3005 - 3008
(2007/10/02)
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- A REEXAMINATION OF THE RETRO-FRIES REARRANGEMENT OF SOME o-HYDROXYKETONES
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The retro-Fries rearrangement, catalyzed by protic and Lewis acids, was studied for some o-hydroxyketones.The results are consistent with the mechanism of an heterolytic cleavage and rearrangement.It appears that, in general, Lewis acids do not induce the retro-Fries rearrangement of o-hydroxyketones.However, in certain cases, it may be brought about the presence of a protic acid generated in situ, from a solvent-catalyst interaction.
- Martin, Robert,Lafrance, Jean Ronald,Demerseman, Pierre
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p. 539 - 548
(2007/10/02)
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- Quinone Dehydrogenation. Oxidation of Benzylic Alcohols with 2,3-Dichloro-5,6-dicyanobenzoquinone
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2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) reacts with primary and secondary aryl-substituted alcohols under mild conditions in dioxane solution to give the corresponding carbonyl compounds in high yields.In contrast to other oxidants, DDQ can be applied advantageously for the oxidation of hydroxyaryl-substituted alcohols.A mechanism involving participation of the phenolic hydroxyl group in the dehydrogenation reaction is discussed.Oxidations of hydroxyaryl-substituted alcohols by DDQ in methanolsolution resulting in the formation of benzoquinones by loss of the hydroxyaryl side chain are interpreted in terms of phenol oxidation.An example of a pyridine-catalyzed Smiles rearrangement of an o-hydroxy-substituted diphenyl ether is reported.
- Becker, Hans-Dieter,Bjoerk, Anders,Adler, Erich
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p. 1596 - 1600
(2007/10/02)
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- BETA-ADRENERGIC BLOCKING AGENTS IN THE 1,2,3-THIADIAZOLE SERIES
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Novel 4-2,3 or 4(3-amino-2-hydroxypropoxy) phenyl!-and 5-2, 3 or 4(3-amino-2-hydroxypropoxy) phenyl!-1,2,3-thiadiazole derivatives which may be further substituted at the C-5 or C-4 position of the thiadiazole ring, respectively, by a lower alkyl, phenyl, trifluoromethyl, carboxy, alkoxycarbonyl, cyano or an aminocarbonyl group, and the pharmaceutically acceptable acid addition salts thereof and processes for the production of such compounds; 4-4(3-t-butylamino-2-hydroxypropoxy) phenyl!-1,2,3-thiadiazole and 5-4(3-t-butylamino-2-hydroxypropoxy) phenyl!-1,2,3-thiadiazole are representative of the class. These compounds possess cardiovascular activity and are useful for the treatment of abnormal heart conditions in mammals.
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