- An umpoled synthon approach to the synthesis of 2-aryloxyphenols
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A convenient three-step method for the preparation of 2-aryloxyphenols from phenols and 2-fluorobenzaldehyde is described. Condensation of phenols with 2-fluorobenzaldehyde produces the intermediate 2-aryloxybenzaldehydes in 83-95% yield. These products rapidly undergo meta-chloroperbenzoic acid (m-CPBA) promoted Baeyer-Villiger oxidation to yield the corresponding 2-aryloxyphenyl formates which are hydrolyzed, without isolation, to give the desired 2-aryloxyphenols in 79-96% yield.
- Yeager,Schissel
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Read Online
- Novel β?hydroxy ketones: Synthesis, spectroscopic characterization, molecular docking, and anticancer activity studies
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In this study, a series of novel β?hydroxy ketone derivatives 3a-o were designed, synthesized, and evaluated for their anticancer activity. The structure of these compounds were characterized by IR, 1H and 13C NMR, mass spectrometry and elemental analysis methods. All the synthesized compounds were screened for anticancer activity against MCF-7 and U87 cells. Among them, compound 3l was appeared to be the most potent compound on both cancer cells; and IC50 dose was determined as 145 μM for MCF-7 cells and 6,6 μM for U87 cells. DNA ladder and Annexin V apoptotic marker tests were used and as a result, 3l caused the initiation of apoptosis on U87 cells. VDAC protein expression increased dramatically after U87 glioblastoma brain cancer cells were treated with compound 3l Additionally, the molecular modeling of these compounds was studied in FLT3 receptor, Estrogen receptor, and PARP2 receptor for the treatment of Acute Myeloid Leukemia (AML), breast cancer, and Glioblastoma (GBM) respectively. Their binding motifs and drug-like properties were investigated, and the results are highlighted in the discussion. Based on the results, compound 3l may have a potential drug candidate profile that can reverse the drug resistance profile.
- Guzel, Mustafa,Kanturk, Gokhan,Kucuk, Hatice Baspinar,Senturk, Ahmet Mesut,Yerlikaya, Serife,Yildiz, Tulay
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- Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones
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We have developed a cerium-photocatalyzed aerobic oxidation of primary and secondary benzylic alcohols to aldehydes and ketones using inexpensive CeCl3 7H2O as photocatalyst and air oxygen as the terminal oxidant.
- K?nig, Burkhard,Kumar, Sumit,Stahl, Jessica,Yatham, Veera Reddy,Yedase, Girish Suresh
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supporting information
p. 1727 - 1732
(2021/08/05)
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- Formation and Disproportionation of Xanthenols to Xanthenes and Xanthones and Their Use in Synthesis
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A facile and versatile strategy employing TiCl4-mediated cyclization followed by a Cannizzaro reaction has been developed for the synthesis of various xanthene derivatives. The reaction proceeded smoothly to afford both xanthenes/xanthones or their sulfur derivatives and tolerated a wide range of electronically diverse substrates. Using this methodology, pranoprofen was synthesized in three steps in 59% overall yield from commercially available starting materials.
- Shi, Zeyu,Chen, Si,Xiao, Qiong,Yin, Dali
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p. 3334 - 3343
(2021/02/05)
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- Pyrimidine onium compound and application thereof
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The invention relates to a pyrimidine onium compound, nitride oxides, salt of the nitride oxides and a composition comprising the compound. The invention further relates to an application of the compound to plant pest control.
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Paragraph 0341-0344
(2019/10/23)
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- HETEROARYL RHEB INHIBITORS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same. Compositions comprising a compound of this invention or a pharmaceutically acceptable derivative thereof and a pharmaceutically acceptable carrier, adjuvant, or vehicle. The amount of the compound in compositions of this invention is such that it is effective to measurably inhibit Rheb, in a biological sample or in a patient.
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Page/Page column 311
(2018/11/10)
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- An organocatalytic method for the synthesis of some novel xanthene derivatives by the intramolecular Friedel-Crafts reaction
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An efficient organocatalytic method for the synthesis of new substituted 9-arylxanthenes (2a-2u) starting from diarylcarbinol compounds with an arenoxy group (1a-1u) has been developed using the intramolecular Friedel-Crafts reaction. The substrates were
- Yildiz, Tülay,Kü?ük, Hatice Ba?pinar
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p. 16644 - 16649
(2017/03/24)
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- Tert -Butoxide mediated cascade desulfonylation/arylation/hydrolysis of cyclic sulfonyimines using diaryliodonium salts: Synthesis of diaryl ether derivatives bearing a 2-aldehyde group
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Cascades of cyclic sulfonyimines mediated by tBuOK with diaryliodonium salts has been developed, giving the diaryl ethers in good yields. Furthermore, bulky ortho-substituted diaryl ethers with an aldehyde group can be obtained easily in comparision with metal-catalyzed protocols.
- Qian, Xiaofei,Han, Jianwei,Wang, Limin
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p. 89234 - 89237
(2016/10/03)
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- RUTHENIUM-BASED METATHESIS CATALYSTS, PRECURSORS FOR THEIR PREPARATION AND THEIR USE
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The invention is directed to ruthenium-based metathesis catalysts of the Grubbs-Hoveyda type. The new 2-aryloxy-substituted ruthenium catalysts described herein reveal rapid initiation behavior. Further, the corresponding styrene-based precursor compounds are disclosed. The catalysts are prepared in a cross-metathesis reaction starting from styrene-based precursors which can be prepared in a cost- effective manner. The new Grubbs-Hoveyda type catalysts are suitable to catalyze ring- closing metathesis (RCM), cross metathesis (CM) and ring- opening metathesis polymerization (ROMP). Low catalyst loadings are necessary to convert a wide range of substrates including more complex and critical substrates via metathesis reactions at low to moderate temperatures in high yields within short reaction times.
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Page/Page column 23; 24
(2014/05/24)
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- Ruthenium-based metathesis catalysts, precursors for their preparation and their use
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The invention is directed to ruthenium-based metathesis catalysts of the Grubbs-Hoveyda type. The new 2-aryloxy-substituted ruthenium catalysts described herein reveal rapid initiation behavior. Further, the corresponding styrene-based precursor compounds are disclosed. The catalysts are prepared in a cross-metathesis reaction starting from styrene-based precursors which can be prepared in a cost-effective manner. The new Grubbs-Hoveyda type catalysts are suitable to catalyze ring-closing metathesis (RCM), cross metathesis (CM) and ring-opening metathesis polymerization (ROMP). Low catalyst loadings are necessary to convert a wide range of substrates including more complex and critical substrates via metathesis reactions at low to moderate temperatures in high yields within short reaction times.
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Paragraph 0075; 0079
(2014/05/20)
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- Fast olefin metathesis: Synthesis of 2-aryloxy-substituted Hoveyda-type complexes and application in ring-closing metathesis
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Four 1-(4-R-phenoxy)-2-ethenylbenzenes (R=NMe2, H, Cl, NO 2) 4a, 4b, 4c and 4d were reacted with the ruthenium complexes [RuCl2(NHC)(3-phenylindenylidene)(py)] in the presence of a protic resin to result in the formation of the respective Hoveyda-type complexes 5a-d {NHC=SIMes [1,3-bis(2,4,6-trimethylphenylimidazolin)-2-ylidene]} and 6a-d {NHC=SIPr [1,3-bis(2,6-diisopropylphenylimidazolin)-2-ylidene]} in 66-84% yield. The lower steric bulk and the decreased donation of the diaryl ether oxygen atoms in complexes 5 and 6 led to rapidly initiating precatalysts. The Ru(II/III) redox potentials of complexes 6 were determined (6a-d: ΔE=0.89-1.08 V). In the crystal structure of 5b two independent molecules were observed in the unit cell, displaying Ru-O distances of 226.6(4) and 230.5(3) pm. The catalytic performance of complexes 5 and 6 in various ring-closing metathesis (RCM) reactions was studied. Catalyst loadings of between 15-200 ppm are sufficient for the formation of >90% yield of the respective cyclic products. Complex 6b catalyzes the formation of N-protected 2,5-dihydropyrroles with up to TON 64,000 and TOF 256,000 h-1, of the N-protected 1,2,3,6- tetrahydropyridines with up to TON 18,200 and TOF 73,000 h-1 and of the N-protected 2,3,6,7-tetrahydroazepines with up to TON 8,100 and TOF 32,000 h-1 with yields ranging between 77 and 96%.
- Kos, Pavlo,Savka, Roman,Plenio, Herbert
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supporting information
p. 439 - 447
(2013/05/21)
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- CINNAMIC ACID HYDROXYAMIDES AS INHIBITORS OF HISTONE DEACETYLASE 8
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Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activy of histone deacetylase 8 (HDAC8). Also described herein are methods of using such HDAC8 inhibitors, alone and in combination with other comp
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Paragraph 00354
(2013/07/19)
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- Wake-promoting agents: Search for next generation modafinil: Part IV
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In search of a next generation molecule to the novel wake promoting agent modafinil, a series of diphenyl ether derived wakefulness enhancing agents (in rat) was developed. From this work, racemic compound 16 was separated into its chiral enantiomers to p
- Louvet, Philippe,Schweizer, Dominique,Gourdel, Marie-Edith,Riguet, Eric,Yue, Christoph,Marcy, Val R.,Lin, Yin Guo,Gruner, John,Lesur, Brigitte,Bacon, Edward R.,Chatterjee, Sankar
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scheme or table
p. 949 - 951
(2012/10/08)
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- Ligand-free copper-catalyzed O-arylation of nitroarenes with phenols
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The first example of ligand-free copper-catalyzed O-arylation of nitroarenes with phenols was developed, achieving unsymmetrical diaryl ethers in moderate to excellent yields. This arylation proceeded smoothly without promotion of the ligands, and displayed great functional group compatibility. Thus, the method represents a new, facile, and cost-effective approach to access unsymmetrical diaryl ethers.
- Chen, Jiuxi,Wang, Xingyong,Zheng, Xingwang,Ding, Jinchang,Liu, Miaochang,Wu, Huayue
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supporting information
p. 8905 - 8907
(2012/10/29)
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- Rearrangement of 2-aryloxybenzaldehydes to 2-hydroxybenzophenones by rhodium-catalyzed cleavage of aryloxy C-O bonds
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Lost in the shuffle: An unprecedented rearrangement of the title compounds proceeds by the simultaneous rhodium-catalyzed cleavage of aryloxy C-O and aldehyde C-H bonds (see scheme). The reaction tolerates the presence of various catalytically reactive substituents such as aryl halides, nitrile, and esters.
- Rao, Honghua,Li, Chao-Jun
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supporting information; experimental part
p. 8936 - 8939
(2011/11/07)
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- A new synthesis of methyl 7 H-Dibenz[b,g]oxocin-6-carboxylates from Morita-Baylis-Hillman adducts of 2-phenoxybenzaldehydes
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A new synthetic method for methyl 7H-dibenz[b,g]oxocin-6-carboxylates by Friedel-Crafts reaction of readily available bromides of Morita-Baylis-Hillman adducts with aluminum chloride has been developed. Georg Thieme Verlag Stuttgart New York.
- Ahn, Sang-Hyun,Jang, Seung Soon,Han, Eun-Gu,Lee, Kee-Jung
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experimental part
p. 377 - 386
(2011/04/22)
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- The coupling of arylboronic acids with nitroarenes catalyzed by rhodium
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The coupling of arylboronic acids with electron-deficient nitroarenes was realized for the first time by using a rhodium(I) catalyst under an air atmosphere, achieving unsymmetrical diaryl ethers with yields ranging from poor to good. From a deuterium labeling experiment, the oxygen atom is derived from ambient water. The efficiency of this reaction was demonstrated by its compatibility with fluoro, bromo, chloro, and trifluoromethyl groups.
- Zheng, Xingwang,Ding, Jinchang,Chen, Jiuxi,Gao, Wenxiao,Liu, Miaochang,Wu, Huayue
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supporting information; experimental part
p. 1726 - 1729
(2011/05/06)
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- Synthesis and antiparasitic and antifungal evaluation of 2′-arylsubstituted-1H,1′H-[2,5′]bisbenzimidazolyl-5-carboxamidines
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A series of 2′-arylsubstituted-1H,1′H-[2,5′]-bisbenzimidazolyl-5-carboxamidines were prepared in a six-step process starting from 4-amino-3-nitrobenzonitrile. The antiparasitic activity against Trypanosoma brucei rhodesiense (T.b.r.), Plasmodium falciparu
- Alp, Mehmet,Goeker, Hakan,Brun, Reto,Yildiz, Sulhiye
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experimental part
p. 2002 - 2008
(2009/10/02)
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- Iron-catalyzed cascade arene-aldehyde addition/cyclizations for the highly efficient synthesis of xanthenes and its analogous: Observation of a C-C bond cleavage in indole-based triarylmethanes
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(Chemical Equation Presented) An efficient, general, and one-pot procedure for the synthesis of multisubstituted xanthene derivatives through Fe(III)-catalyzed reactions of 2-aryloxybenzaldehydes with electron-rich arenes has been developed. This method offers several advantages such as high selectivities, mild reaction conditions, and easily accessible starting materials. A mechanistic study revealed that a C-C bond cleavage of a triarylmethane intermediate might be involved in the domino process.
- Li, Hongfeng,Yang, Jingyu,Liu, Yuanhong,Li, Yanzhong
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body text
p. 6797 - 6801
(2009/12/30)
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- 1-(2-Phenoxyphenyl)methanamines: SAR for dual serotonin/noradrenaline reuptake inhibition, metabolic stability and hERG affinity
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A novel series of 1-(2-phenoxyphenyl)methanamines is disclosed, which possess selective dual 5-HT and NA reuptake pharmacology. Analogues with good human in vitro metabolic stability, hERG selectivity and passive membrane permeability were identified.
- Whitlock, Gavin A.,Blagg, Julian,Fish, Paul V.
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p. 596 - 599
(2008/09/20)
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- An aryl to imidoyl palladium migration process involving intramolecular C-H activation
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Biologically interesting fluoren-9-one and xanthen-9-one derivatives have been prepared by a novel aryl to imidoyl palladium migration, followed by intramolecular arylation. The fluoren-9-one synthesis appears to involve both a palladium migration mechanism and a C-H activation process proceeding through an unprecedented organopalladium(IV) hydride intermediate. The results from deuterium labeling experiments are consistent with the proposed dual mechanism.
- Zhao, Jian,Yue, Dawei,Campo, Marino A.,Larock, Richard C.
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p. 5288 - 5295
(2008/02/02)
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