- Ac2O-Mediated Dearylacetylative Dimerization of 2-Arylacetyl-1-naphthols: Synthesis of Naphtho[1,2-b]furan-3-ones
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A novel and efficient route for the synthesis of 2-Aryl-2-naphthyl naphtho[1,2-b]furan-3-ones is described via NaH/Ac2O-mediated dearylacetylative dimerization of 2-Arylacetyl-1-naphthols in refluxing THF under open-flask conditions. A plausibl
- Chang, Meng-Yang,Chen, Kuan-Ting,Chen, Shin-Mei,Hsiao, Yu-Ting
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p. 3605 - 3616
(2020/03/23)
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- Asymmetric Transfer Hydrogenation of o-Hydroxyphenyl Ketones: Utilizing Directing Effects That Optimize the Asymmetric Synthesis of Challenging Alcohols
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A systematic range of o-hydroxyphenyl ketones were reduced under asymmetric transfer hydrogenation conditions using the C3-tethered catalyst 2. Two directing effects, i.e., an o-hydroxyphenyl coupled to a bulky aromatic on the opposite side of the ketone substrate, combine in a matched manner to deliver reduction products with very high enantiomeric excess.
- Clarkson, Guy J.,Wills, Martin,Zheng, Ye
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supporting information
(2020/05/05)
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- Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarinviaa TsOH-mediated tandem reaction
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A concise and efficient method for the synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarin using available 1-(2-hydroxyphenyl)-2-phenylethanone and Meldrum's acid has been developed. This transformation involved a tandem aldol reaction/lactonization/Friedel-Crafts reaction to form a lactone ring and a benzene ring. It showed high atom economy with water and acetone as the byproducts. Mechanism studies demonstrated two roles of Meldrum's acid: (i) as the reagent for the tandem reaction, and (ii) as the catalyst for the Friedel-Crafts reaction. Moreover, the hydroxyl group of 7-hydroxy-6H-naphtho[2,3-c]coumarin was further functionalized efficiently by arylethynyl, aryl, and cyano groups to furnish D-π-A compounds with excellent fluorescence emissions (ΦF= 0.14-0.78).
- Li, Chenyu,Liang, Yong,Ma, Zhishuang,Wang, Ding,Wang, Nana,Wang, Tao,Zhang, Zunting
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supporting information
p. 10369 - 10372
(2020/09/16)
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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,Zhang, Yao,Zhang, Qing-Wen,Yin, Qin,Zhang, Xumu
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p. 5321 - 5325
(2020/02/28)
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- Palladium-catalyzed direct C-H arylation of 2-hydroxybenzaldehydes with organic halides in neat water
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The palladium-catalyzed cross-coupling of 2-hydroxybenzaldehydes with organic halides proceeds in the presence of n-Bu4NBr in H2O producing the corresponding 2-hydroxybenzophenones in high yields.
- Nowrouzi, Najmeh,Motevalli, Somayeh,Tarokh, Dariush
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p. 224 - 230
(2015/02/05)
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- Ascorbic Acid Promoted Oxidative Arylation of Vinyl Arenes to 2-Aryl Acetophenones without Irradiation at Room Temperature under Aerobic Conditions
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A convenient and general protocol for oxidative arylation of vinyl arenes by aryl radicals generated in situ from arene diazonium fluoroborates promoted by ascorbic acid in air at room temperature has been developed in the absence of any additive and visible light irradiation. A series of diversely substituted 2-aryl acetophenones have been obtained in good yields by this procedure.
- Majhi, Biju,Kundu, Debasish,Ranu, Brindaban C.
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supporting information
p. 7739 - 7745
(2015/08/18)
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- 3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators
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Following the recent identification of the naturally occurring 3-ylidene-4,5-dihydrophthalide ligustilide and its oxidation product dehydroligustilide as novel TRPA1 modulators, a series of seventeen 3-ylidenephthalides was synthesized and tested on TRPA1 and TRPM8 channels. Most of these compounds acted as strong modulators of the two channel types with EC50 and/or IC50 values distinctly lower than those of the reference compounds.
- Ortar, Giorgio,Schiano Moriello, Aniello,Morera, Enrico,Nalli, Marianna,Di Marzo, Vincenzo,De Petrocellis, Luciano
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p. 5614 - 5618
(2013/10/01)
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- Microwave-assisted efficient synthesis of 2-hydroxydeoxybenzoins from the alkali degradation of readily prepared 3-aryl-4-.hydroxycoumarins in water
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This paper describes an operationally simple, green and efficient approach for the synthesis of 2-hydroxydeoxybenzoins bearing diverse substituents from the microwave-assisted alkali degradation of 3-aryl- 4-hydroxycoumarins in water. The latter compounds
- Zhou, Zhong-Zhen,Yan, Guang-Hua,Chen, Wen-Hua,Yang, Xue-Mei
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p. 1166 - 1172
(2014/01/06)
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- Tandem gold-catalyzed hydrosilyloxylation-aldol and -Mannich reaction with alkynylaryloxysilanols in 6-exo mode
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The tandem gold-catalyzed hydrosilyloxylation-aldol and hydrosilyloxylation-Mannich reactions were developed through the formation of an enol silyl ether catalytically generated in situ from alkynylaryloxysilanols in the 6-exo mode in one reaction vessel. Copyright
- Lee, Euichul,Ryu, Taekyu,Park, Youngchul,Park, Sangjune,Lee, Phil Ho
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p. 1585 - 1596
(2013/06/27)
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- Intermolecular C-O addition of carboxylic acids to arynes: Synthesis of o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones
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An efficient and simple route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed utilizing readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl tr
- Dubrovskiy, Anton V.,Larock, Richard C.
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p. 2789 - 2798
(2013/03/29)
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- NOVEL KINASE MODULATORS
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The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.
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Page/Page column 92-93
(2011/06/10)
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- One step synthesis of 2-hydroxymethylisoflavone and their osteogenic activity
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An efficient one step synthesis of new 2-hydroxymethylisoflavone is reported. A series of deoxybenzoin was subjected to cyclization with glyoxal in the presence of basic condition (KOH/EtOH) to afford the 2-hydroxymethyl isoflavone. The structures of comp
- Kumar, Manmeet,Rawat, Preeti,Kureel, Jyoti,Singh, Anuj Kumar,Singh, Divya,Maurya, Rakesh
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experimental part
p. 1706 - 1709
(2011/05/11)
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- Intermolecular C-O addition of carboxylic acids to arynes
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(Figure Presented) A novel, efficient, and expedient route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed starting from readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl triflates.
- Dubrovskiy, Anton V.,Larock, Richard C.
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supporting information; experimental part
p. 3117 - 3119
(2010/08/22)
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- TMSOTf-promoted addition of alkynes to aldehydes: A novel synthesis of chroman-4-ones
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A novel synthetic method to prepare chalcones 2 and chroman-4-ones 3 by TMSOTf-promoted addition of alkynes 1 to various aldehydes has been developed. The ratios of chalcones 2, chroman-4-ones 3 and hydrated products 4 varied depending upon the substituents R (nBu, phenyl, H and TMS) on the alkynes 1. We also describe the transformation of the chalcones 2 to the corresponding chroman-4-ones 3 under basic conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Ji, Yeon Park,Ullapu, Punna Reddy,Choo, Hyunah,Jae, Kyun Lee,Min, Sun-Joon,Ae, Nim Pae,Kim, Youseung,Baek, Du-Jong,Yong, Seo Cho
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experimental part
p. 5461 - 5469
(2009/05/07)
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- Targeting the gatekeeper residue in phosphoinositide 3-kinases
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A single residue in the ATP binding pocket of protein kinases-termed the gatekeeper-has been shown to control sensitivity to a wide range of small molecule inhibitors (Chem. Biol. 2004, 11, 691; Chem. Biol. 1999, 6, 671). Kinases that possess a small side chain at this position (Thr, Ala, or Gly) are readily targeted by structurally diverse classes of inhibitors, whereas kinases that possess a larger residue at this position are broadly resistant. Recently, lipid kinases of the phosphoinositide 3-kinase (PI3-K) family have become the focus of intense research interest as potential drug targets (Chem. Biol. 2003, 10, 207; Curr. Opin. Pharmacol. 2003, 3, 426). In this study, we identify the residue that corresponds structurally to the gatekeeper in PI3-Ks, and explore its importance in controlling enzyme activity and small molecule sensitivity. Isoleucine 848 of p110α was mutated to alanine and glycine, but the mutated kinase was found to have severely impaired enzymatic activity. A structural bioinformatic comparison of this kinase with its yeast orthologs identified second site mutations that rescued the enzymatic activity of the I848A kinase. To probe the dimensions of the gatekeeper pocket, a focused panel of analogs of the PI3-K inhibitor LY294002 was synthesized and its activity against gatekeeper mutated and wild-type p110α was assessed.
- Alaimo, Peter J.,Knight, Zachary A.,Shokat, Kevan M.
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p. 2825 - 2836
(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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- 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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- 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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- Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones
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The carbonylative cross-coupling reaction of arylboronic acids with aryl electrophiles (ArI, ArBr, and ArOTf) to yield unsymmetrical biaryl ketones was carried out in anisole at 80°C in the presence of a palladium catalyst and a base. The reaction selectively proceeded under an atmospheric pressure of carbon monoxide when PdCl2(PPh3)2 (3 mol %)/K2CO3 (3 equiv) were used for aryl iodides and PdCl2(dppf) (3 mol %)/K2CO3 (3 equiv)/KI (3 equiv) for the bromides or the triflates. The carbonylation of arylboronic acids with benzyl halides gave aryl benzyl ketones.
- Ishiyama, Tatsuo,Kizaki, Hiroe,Hayashi, Takahiro,Suzuki, Akira,Miyaura, Norio
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p. 4726 - 4731
(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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- 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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- New procedures for the preparation of isoflavones with unsubstituted ring A
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Isoflavones with unsubstituted ring A have been synthesized either by the ring closure of 2-hydroxydeoxybenzoins or by the dehydroxylation of 7-hydroxyisoflavones. 7-Mercaptoisoflavones have also been prepared.
- Levai,Sebok
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p. 1735 - 1750
(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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- Influence of the β-Substitution on the Photochemistry of α,2-Diacetoxystyrenes. Irradiatin of Phenyl, Vinyl, and Benzyl Derivatives
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β-Substitution shows a pronounced influence on the photochemistry of α,2-diacetoxystyrenes.As in the case of the parent compound, intramolecular cyclization with participation of the neighbouring 2-acetoxy group takes place upon irradiation of the enol esters 4a-c; however other processes are also observed, depending on the substrate.The phenyl derivative 4a gives the E isomer 7a and the phenanthrene 9.The vinyl derivative 4b also undergoes cis-trans isomerization and/or photooxidation, to afford 7b and 10.Finally, a 1,4-acyl migratin occurs in the benzyl derivative 4c, whereby the 1,4-diketone 12 is formed.
- Alvaro, Mercedes,Baldovi, Vicenta,Garcia, Hermenegildo,Miranda, Miguel, A.,Primo, Jaime
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p. 267 - 274
(2007/10/02)
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- Chemotherapeutic agents
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A method of treating or preventing viral infections, in particular rhinovirus infections comprising the administration of an effective amount of a 2-phenyltetralin derivative or a heterocyclic analogue thereof. Pharmaceutical compositions containing these compounds, and some novel compounds are also disclosed.
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- ALKALINE DEGRADATION OF PARENT CHROMONOID COMPOUNDS (CHROMONE, FLAVONE, ISOFLAVONE)
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Ring-opening and degradation processes of parent flavonoid compounds under alkaline conditions have been studied by means of thin-layer chromatography.The direction of the splitting has been found dependent on the OH(1-) ion concentration.In the case of isoflavone salicylic acid was present in the reaction mixture, indicating a novel type of degradation of isoflavonoids.
- Zsuga, Miklos,Kiss, Aniko
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p. 485 - 490
(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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