- Synthesis of xanthones from 4-(2-phenoxyphenyl)-1-tosyl-1H-1,2,3-triazole via rhodium-catalyzed annulation/oxidation
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A series of xanthone derivatives were synthesized by rhodium-catalyzed cycloaddition and sequential oxidation. The derivatives synthesized for excellent yields, including electron-withdrawing and electron-donating substituents, demonstrated the wide applicability of the proposed approach. The xanthones synthesized with different substituent electron effects may go through the same intermediate via two cycloadditions. It is highlighted that the protocol was exemplified by its successful integration into a one-pot synthesis directly from 1-ethynyl-2-phenoxybenzene. We believe that the current method may be an attractive option for the synthesis of xanthone and its derivatives.
- Anna,Chen, Zhaohang,Gao, Juanhong,Li, Chao,Qiao, Hongwei,Zhu, Mengyao
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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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- Regioselective Bromine/Magnesium Exchange for the Selective Functionalization of Polyhalogenated Arenes and Heterocycles
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Using the bimetallic combination sBu2Mg?2 LiOR (R=2-ethylhexyl) in toluene enables efficient and regioselective Br/Mg exchanges with various dibromo-arenes and -heteroarenes under mild reaction conditions and provides bromo-substituted magnesiu
- Desaintjean, Alexandre,Haupt, Tobias,Bole, Leonie J.,Judge, Neil R.,Hevia, Eva,Knochel, Paul
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supporting information
p. 1513 - 1518
(2020/11/30)
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- Ultraviolet-light-induced aerobic oxidation of benzylic C(sp3)-H of alkylarenes under catalyst- and additive-free conditions
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A mild and efficient system has been discovered for the synthesis of α-aryl carbonyl compounds via oxidation of benzylic C–H to C[dbnd]O bonds. This ultraviolet-light-mediated oxygenation reaction exhibited excellent substrate scope including various xanthenes, thioxanthenes and 9, 10-dihydroacridines and afforded the corresponding ketones with good to excellent yields under catalyst- and additive-free conditions at room temperature.
- Zhou, Jiacheng,Li, Meichao,Li, Tianci,Li, Chunmei,Hu, Xinquan,Jin, Liqun,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu
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- Synthesis of xanthones, thioxanthones and Acridones by a metal-free photocatalytic oxidation using visible light and molecular oxygen
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9H-Xanthenes, 9H-thioxanthenes and 9,10-dihydroacridines can be easily oxidized to the corresponding xanthones, thioxanthones and acridones, respectively, by a simple photo-oxidation procedure carried out using molecular oxygen as oxidant under the irradiation of visible blue light and in the presence of riboflavin tetraacetate as a metal-free photocatalyst. The obtained yields are high or quantitative.
- Chinchilla, Rafael,Torregrosa-Chinillach, Alejandro
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- A Green Nanopalladium-Supported Catalyst for the Microwave-Assisted Direct Synthesis of Xanthones
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We report an efficient, selective, rapid and eco-friendly protocol for the one-step synthesis of a small xanthone library via an intermolecular catalytic coupling from readily available salicylaldehydes and 1,2-dihaloarenes under ligand-free conditions. To achieve this advantageous direct annulation, we used a novel recoverable palladium nanocatalyst supported on a green biochar under microwave irradiation. Unlike other existing palladium-based approaches, our synthetic strategy showed a greater operational simplicity, drastic reduction in reaction times, and an excellent tolerance to diverse functional groups. The reaction proceeds in very good yields and with high regioselectivity. The novel heterogeneous catalyst can be recycled and reused up to four times without significant loss of activity.
- Diez, Alejandra S.,Gerbino, Darío C.,Mendioroz, Pamela,Steingruber, H. Sebastián
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supporting information
p. 619 - 628
(2020/02/13)
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- Ultraviolet light promoted synthesis method of xanthone compounds
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The invention discloses an ultraviolet light promoted synthesis method of a xanthone compound. The method comprises the steps: by taking a xanthene compound as a reaction substrate and oxygen in air as an oxidant, carrying out a reaction on the reaction substrate in an organic solvent at normal temperature under the condition of 380-385 nm ultraviolet irradiation, and after the reaction is finished, carrying out separation treatment to obtain the xanthone compound. According to the synthesis method disclosed by the invention, a traditional heating reaction is replaced by an illumination reaction, so that energy sources can be saved; no catalyst is used.
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Paragraph 0047; 0048
(2020/05/05)
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- Benzylic oxidation and functionalizations of xanthenes by ligand trasfer reactions of hypervalent iodine reagents
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The benzylic oxidation, amidation, and unprecedented heteroarylation proceed at room temperature using iodosobenzene, (sulfonylimido)iodobenzenes, and diaryliodonium(III) salts are described for the direct Csp3-H functionalizations of xanthene molecules. This study has demonstrated that hypervalent iodine reagents serve as unified synthetic tools for versatile xanthene Csp3-H transformations based on the radical and SET oxidation processes.
- Dohi, Toshifumi,Ito, Motoki,Kita, Yasuyuki,Komiyama, Keina,Ueda, Shohei,Yamaoka, Nobutaka
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- Visible-Light-Induced Aerobic Oxidation of Benzylic C(sp 3)-H of Alkylarenes Promoted by DDQ, tert -Butyl Nitrite, and Acetic Acid
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A visible-light photocatalytic aerobic oxidation of benzylic C(sp 3)-H bonds proceeded in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tert -butyl nitrite, and acetic acid. Advantages of this aerobic oxidation method include its relatively mild conditions, the use of visible-light irradiation instead of conventional thermal methods, the use of a low catalyst loading, and the ability to oxidize a range of alkylarenes, including xanthenes, thioxanthenes, and 9,10-dihydroacridines, to the corresponding ketones in excellent yields.
- Pan, Decheng,Wang, Yiqing,Li, Meichao,Hu, Xinquan,Sun, Nan,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu
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p. 218 - 224
(2019/01/14)
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- Cu(0)/Selectfluor system-catalyzed intramolecular Csp2-H/Csp2-H cross-dehydrogenative coupling (CDC)
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A Cu(0)/Selectfluor system-catalyzed intramolecular Csp2-H/Csp2-H bond cross-dehydrogenative coupling of 2-aryloxybenzaldehydes is described. A variety of substituted xanthone derivatives are synthesized in moderate to excellent yields. Reaction can also be extended to the synthesis of 9H-thioxanthen-9-one 10,10-dioxide and phenanthridin-6(5H)-ones, respectively.
- Bao, Hanyang,Hu, Xiaojun,Zhang, Jian,Liu, Yunkui
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- Synthetic method for xanthone and xanthone derivatives
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The present invention discloses a synthetic method for xanthone and xanthone derivatives. The synthetic method comprises the following steps: using 2-aryloxybenzaldehyde represented by a formula I inthe description as a raw material, performing a reaction at the temperature of 80-110 DEG C for 12-36h in an organic solvent under the actions of a copper catalyst and an oxidant, and performing separation purification on an obtained reaction liquid to obtain the xanthone represented by a formula II in the description and the xanthone derivatives. The synthetic method provided by the invention hasthe advantages that the raw materials are cheap and easy to obtain, the method is environmentally friendly, the reaction conditions are mild, the target substrate is synthesized high efficiently, theuniversality of the functional groups is good, the operation is simple and convenient and the like.
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Paragraph 0094; 0095; 0096
(2018/04/02)
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- Concise synthesis of xanthones by the tandem etherification—Acylation of diaryliodonium salts with salicylates
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An efficient synthetic method for multi-substituted xanthones was developed. The reaction of diaryliodonium salts and salicylates was employed for the preparation of the xanthones. This method proceeded through an intermolecular etherification-acylation t
- Liu, Gaoxiaozheng,Wu, Chao,Chen, Bifeng,He, Ru,Chen, Chao
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p. 985 - 988
(2018/04/05)
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- Method for preparing polysubstituted oxoxanthone derivative
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The invention discloses a method for preparing a polysubstituted oxoxanthone derivative. The method comprises the following steps: adding a diaryl iodide compound in a reactor, after extracting and changing nitrogen, adding a salicylate derivative compound and a solvent under the protection of the nitrogen, carrying out heating reaction, and after reaction, extracting and purifying a reactant to obtain the polysubstituted oxoxanthone derivative, wherein the reaction temperature is 40-150 DEG C, and the reaction time is 1-24h. The preparation method of the polysubstituted oxoxanthone derivative, provided by the invention, is scientific and reasonable, and a synthesis method has the characteristics of simpleness, high yield, easiness in purification of a product and the like.
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Paragraph 0035; 0036; 0037; 0037; 0038; 0039; 0040-0049
(2017/08/29)
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- Organic electroluminescence material and organic photoelectric device
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The invention provides a compound with a structure as shown in formula I. The invention also provides an application of the compound in an organic photoelectric device and the organic photoelectric device. The compound provided by the invention has a ther
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Paragraph 0129; 0130
(2017/07/21)
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- CBr4 promoted intramolecular aerobic oxidative dehydrogenative arylation of aldehydes: application in the synthesis of xanthones and fluorenones
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A simple and practical carbon tetrabromide promoted intramolecular aerobic oxidative dehydrogenative coupling reaction has been developed to provide a straightforward ring closure protocol for 2-aryloxybenzaldehydes to furnish xanthones. The reaction was performed under metal-, additive- and solvent-free conditions with good tolerance of functional groups. The present method is also applicable to the synthesis of fluorenones by using 2-arylbenzaldehydes as substrates. Preliminary studies of the reaction mechanism indicated that the reaction may proceed through a radical pathway.
- Tang, Jing,Zhao, Shijun,Wei, Yuanyuan,Quan, Zhengjun,Huo, Congde
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supporting information
p. 1589 - 1592
(2017/02/23)
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- FeCl3 and ether mediated direct intramolecular acylation of esters and their application in efficient preparation of xanthone and chromone derivatives
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The direct intramolecular acylation of esters was developed by using the combined system of FeCl3 with Cl2CHOCH3. This unique cooperative system offered a new and efficient approach to biologically important xanthone and chromone derivatives with regioselectivity. Examples were reported, and control experiments were carried out to examine the effect of the benzyl esters and Cl2CHOCH3.
- Jiang, Neng,Li, Su-Yi,Xie, Sai-Sai,Yao, Hequan,Sun, Hongbin,Wang, Xiao-Bing,Kong, Ling-Yi
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supporting information
p. 63632 - 63641
(2015/02/19)
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- New Methodology for the Synthesis of Xanthones
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Methods are provided for forming a xanthone derivative via reacting a 2-substituted benzaldehyde with a phenol derivative to form the xanthone derivative.
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Paragraph 0026; 0043
(2014/05/07)
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- One-step synthesis of xanthones catalyzed by a highly efficient copper-based magnetically recoverable nanocatalyst
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A versatile and highly efficient strategy to construct a xanthone skeleton via a ligand-free intermolecular catalytic coupling of 2-substituted benzaldehydes and a wide range of phenols has been developed. For this purpose, a novel and magnetically recoverable catalyst consisting of copper nanoparticles on nanosized silica coated maghemite is presented. The reaction proceeds smoothly with easy recovery and reuse of the catalyst. The methodology is compatible with various functional groups and provides an attractive protocol for the generation of a small library of xanthones in very good yield.
- Menendez, Cintia A.,Nador, Fabiana,Radivoy, Gabriel,Gerbino, Dario C.
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supporting information
p. 2846 - 2849
(2014/06/23)
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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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- Cross dehydrogenative coupling via base-promoted homolytic aromatic substitution (BHAS): Synthesis of fluorenones and xanthones
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Cross dehydrogenative coupling reactions occurring via base-promoted homolytic aromatic substitutions (BHASs) are reported. Fluorenones and xanthones are readily prepared via CDC starting with readily available ortho-formyl biphenyls and ortho-formyl biphenylethers, respectively. The commercially available and cheap tBuOOH is used as an oxidant. Initiation of the radical chain reaction is best achieved with small amounts of FeCp2 (0.1 or 1 mol %).
- Wertz, Sebastian,Leifert, Dirk,Studer, Armido
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p. 928 - 931
(2013/03/28)
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- Copper-catalyzed ortho-acylation of phenols with aryl aldehydes and its application in one-step preparation of xanthones
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In the presence of triphenylphosphine, copper(ii) chloride can catalyze an intermolecular ortho-acylation reaction of phenols with aryl aldehydes. The reaction proceeds smoothly with a wide range of starting materials, and furthermore, it can be used to s
- Hu, Jun,Adogla, Enoch A.,Ju, Yong,Fan, Daping,Wang, Qian
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supporting information
p. 11256 - 11258
(2013/01/15)
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- Rhodium-catalyzed xanthone formation from 2-aryloxybenzaldehydes via cross-dehydrogenative coupling (CDC)
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A concise and straightforward strategy to construct a xanthone skeleton via an intramolecular cross-dehydrogenative coupling (CDC) of 2- aryloxybenzaldehydes has been developed. The reaction proceeded smoothly without any need of preactivation of the aldehyde group. It can tolerate various functional groups and provides an applicable protocol to construct a wide range of xanthone derivatives.
- Wang, Ping,Rao, Honghua,Hua, Ruimao,Li, Chao-Jun
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supporting information; scheme or table
p. 902 - 905
(2012/04/05)
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- XANTHONE COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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An organic light-emitting device that realizes high-emission efficiency and low-driving voltage is provided. The organic light-emitting device contains a xanthone compound represented by general formula [1].
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Page/Page column 40-41
(2012/05/20)
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- Photochemically amplified detection of molecular recognition events: An ultra-sensitive fluorescence turn-off binding assay
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Amplified fluorescence quenching methodology based on massive autocatalytic photo-unmasking of a dual function sensitizer-quencher is developed and adopted for photoassisted ultra-sensitive detection of molecular recognition events. The resulting binding
- Gustafson, Tiffany P.,Metzel, Greg A.,Kutateladze, Andrei G.
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p. 4752 - 4755
(2011/08/08)
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- Xanthones in heterocyclic synthesis. An efficient route for the synthesis of C-3 o-Hydroxyaryl substituted 1, 2-benzisoxazoles and their N-oxides, potential scaffolds for angiotensin(II) antagonist hybrid peptides
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Regioselective substitution of xanthone and its nucleophilic cleavage allow the synthesis of C-3 ohydroxyaryl substituted 1, 2-benzisoxazoles or their V-oxides by cyclodehydration or oxidative cyclization of their corresponding ketoxime precursors, respectively. Molecular modeling analysis and 1H NMR spectra indicate an intramolecular H-bonding engaging phenol OH and the isoxazole ring N atom. The Japan Institute of Heterocyclic Chemistry.
- Gardikis, Yiannis,Tsoungas, Petros G.,Potamitis, Constantinos,Zervou, Maria,Cordopatis, Paul
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experimental part
p. 1077 - 1091
(2011/06/19)
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- Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates
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The reaction of silylaryl triflates, CsF, and ortho-heteroatom-substituted benzoates affords a general and efficient way to prepare biologically interesting xanthones, thioxanthones, and acridones. This chemistry presumably proceeds by a tandem intermolecular nucleophilic coupling of the benzoate with an aryne and a subsequent intramolecular electrophilic cyclization.
- Zhao, Jian,Larock, Richard C.
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p. 583 - 588
(2007/10/03)
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