cas 82-05-3, Benzanthrone | Articles data

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Synthesis and Characterization of Polysubstituted Dibenzopyrenes as Charge-Transporting Materials
A new class of benzopyrene-based semiconducting molecules is prepared and characterized. A four-step protocol involving Suzuki coupling and aromatic dehydrogenation reactions renders the new unsymmetrical framework. Introduction of various substituents at the dibenzopyrene framework modulates mainly the optoelectronic properties rather than the packing motif. Single-crystal field-effect transistors fabricated from these materials show a mobility ranging from 0.7 to 3.2 cm2/(V s). The highest mobility, 3.2 cm2/(V s), with an on/off ratio of 104-105 was achieved for 11-methoxy-8-(4-methoxyphenyl)dibenzo[a,e]pyrene.
Kumar, Sushil,Ho, Man-Tzu,Tao, Yu-Tai
p. 4876 - 4879
(2016)
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Novel production method of phenanthrone (by machine translation)
The invention relates to the field of, fine chemical engineering, in particular to a, preparation method of phenanthrapyone: and, specifically, relates, to a method for preparing phenylanthrone, in particular, to H the following steps of: transferring a catalyst and a solvent to a pressure reaction kettle through a catalyst and a solvent in an anthraquinone process. 2 After the reaction completion of the reaction was; completed, the reaction solution was, cooled and the reaction solution, was left to H leave the remainder. 2 Compared with the prior, art, the method, disclosed by the invention has second the advantages; that the raw material recycling rate is; high second the process is, easy to control, the cost is; low, and the product quality, is obviously improved . (by machine translation)
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Paragraph 0031-0043

(2020/01/25)

Benzanthrone derivative and preparation method thereof and application thereof in functional pigments
The invention discloses a benzanthrone derivative and a preparation method thereof. The general formula is shown as a formula I or IV, formula I or IV, R1, R2, R3 is independently selected from hydrogen, halogen, an ester group, an acyl group, a branched-chain or straight-chain C1-C20 alkyl group, a straight-chain or branched-chain C1-C20 alkoxy group, a branched-chain or straight-chain perfluoroC1-C20 alkyl group, a branched-chain or straight-chain perfluoroC1-C20 alkoxy group, a substituted or unsubstituted C4-C40 aryl group, and a substituted or unsubstituted C4-C40 heteroaryl group. The benzanthrone derivative with a novel structure provided by the invention is simple in preparation method, non-toxic and harmless, has yellow fluorescence, can be used as a potential organic functional material, and is an important dye intermediate.
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(2020/07/24)

Palladium-Catalyzed Site-Selective Benzocyclization of Naphthoic Acids with Diaryliodonium Salts: Efficient Access to Benzanthrones
Dual activation of both C-I and vicinal C-H bonds of diaryliodonium salts allowing for diarylation is a subject of rapid construction of π-extended frameworks. Here, we report palladium-catalyzed cascade of C8-arylation/intramolecular Friedel-Crafts acylation of α-naphthoic acids in the synthesis of benzanthrone derivatives. The step-economical protocol tolerates various substrates, which resulted in a potential molecular library for developing functional polycyclic scaffolds. The approach relies on the synergistic action of strong acid with palladium catalysts to form two bonds in a one-pot procedure.
Xue, Chenwei,Wang, Limin,Han, Jianwei
p. 15406 - 15414
(2020/12/23)

Compound with anthrene structure and application of compound in organic light emitting diode devices
The invention discloses a compound with an anthrene structure and application of the compound, and belongs to the technical field of semiconductors. The structure of the compound is represented by a formula (1) as shown in the description. The invention further discloses the application of the compound. The compound takes anthrene as a core and has high carrier mobility and good carrier equilibrium capability. Meanwhile, the compound has relatively high glass transition temperature, high molecular thermal stability and suitable HOMO and LUMO energy levels. The compound serves as a main body material of a luminescent layer and can generate a triplet-triplet coupling effect, and thus a utilization rate of triplet states is effectively increased. By adopting device structures based on the compound, the efficiency of OLED devices can be effectively improved, and the service lives of the OLED devices can be effectively prolonged.
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Paragraph 0065-0067; 0078

(2020/03/16)

The linkage between reversible Friedel–Crafts acyl rearrangements and the Scholl reaction
Friedel–Crafts acyl rearrangements in PPA (at 80–240?°C) and Scholl reactions in AlCl3/NaCl (at 140–220?°C) of benzoylnaphthalenes and fluorobenzoylnaphthalenes have been studied experimentally as a function of temperature and time and computationally. 1BzNA, 2BzNA, 1-4FBzNA, 2-4FBzNA, 1-3FBzNA, 2-3FBzNA, 1-2FBzNA, and 2-2FBzNA were synthesized by classical Friedel–Crafts acylations of naphthalene with benzoyl chloride, benzene with 2-naphthoyl chloride,?fluorobenzene with 1- and 2-naphthoyl chlorides and of naphthalene with fluorobenzoyl chlorides, and served as substrates in the investigation. Their structures have been determined by X-ray crystallography and verified by their 1H-, 13C-, and 19F-NMR spectra. 1BzNA, 1-4FBzNA, 1-3FBzNA, and 2-2FBzNA crystallized as the E-diastereomers, whereas 2BzAN, 1-2FBzAN, 2-4FBzAN, and 2-3FBzAN crystallized as the Z-diastereomers. The deviations of the carbonyl group from the naphthyl plane were higher as compared with the deviations from the phenyl plane and were considerably higher in the α-naphthyl ketones than in the β-naphthyl ketones. Intermolecular interactions due to C–H···O and/or C–H···F contacts in the crystal structures of 1E-4FBzNA and 1E1′E-3FBzAN have been revealed. 1BzNA rearranged in PPA under argon to 2BzNA via deacylation to naphthalene (e.g., 140?°C, 10?h) and underwent a regioselective intramolecular cyclodehydrogenation at high temperatures to the Scholl reaction product 7H-benz[de]anthracen-7-one (BdeAN) (e.g., 200?°C, 6?h). At 80?°C, benzene was isolated. 2BzNA underwent in PPA deacylation to naphthalene (e.g., 160?°C, 6?h) and an intramolecular cyclodehydrogenation to BdeAN at high temperatures (e.g., 220?°C, 6?h), necessarily via the putative intermediate 1BzNA. Higher yields of the acyl rearrangement and the Scholl reaction products were obtained under oxygen. 1-4FBzNA and 2-4FBzNA reacted in PPA analogously to 1BzNA and 2BzNA, respectively, with the following exceptions: 2-4FBzNA underwent an acyl rearrangement in PPA to 1-4FBzNA at 260–300?°C, without any formation of the Scholl reaction product 10FBdeAN. 1-4FBzNA also did not yield 10FBdeAN. 1-2FBzNA and 2-2FBzNA behaved similarly. The formation of naphthalene and benzene in the deacylation steps indicated cleavages of both the 1- and 2-naphthyl–benzoyl bonds and the 1- and 2-naphthoyl–phenyl bonds to give naphthalene and benzoylium cation and benzene and 1- and 2-naphthoylium cation, respectively. At 80–100?°C, 1-2FBzNA, 1-3FBzNA, and 1-4FBzNA underwent deacylations to fluorobenzene in PPA, followed by reacylation, each giving a mixture of the three 1-fluorobenzoylnaphthalenes. 2FBzNA, 2-3FBzNA, and 2-4FBzNA behaved similarly, each giving a mixture of the three 2-fluorobenzoylnaphthalenes. The results taken together verified the reversibility of the 1-BzNA?2BzNA acyl rearrangements in PPA. The Scholl reaction (AlCl3/NaCl) of 1BzNA (e.g., at 140?°C) gave BdeAN and 2BzNA, whereas 2BzNA gave only BdeAN (at 200–220?°C). 1-4FBzNA and 2-4FBzNA gave (at 200–220?°C) only 2-4FBzNA and 1-4FBzNA, respectively. All the six FBzNA isomers failed to undergo Scholl reaction cyclodehydrogenations to give any FBdeAN isomer. A linkage between the Friedel–Crafts acyl rearrangements and the Scholl reaction has thus been established. A systematic DFT study at B3LYP/6-311(d,p)/PCM (formic acid)) substantiated the predicted mechanism and the reversibility of the acyl rearrangements of benzoylnaphthalenes, in which 1BzNA and 2BzNA are the kinetically controlled and the thermodynamically controlled products, respectively. The DFT-calculated Gibbs free-energy of the transition-state (1Z-1BzNH+ ?? 2σ-2BzNA) in the Friedel–Crafts acyl rearrangement of 1Z-BzNA is considerably lower than the transition state of the cyclization step in the arenium-cation mechanism of the Scholl reaction, in line with experiment, which indicated higher temperatures for the Scholl reaction. DFT calculations of the dication pathway of the Scholl reaction of the E- and Z-diastereomers/conformers of 1BzNA confirmed the preference of the formation of BdeAN versus BaFL, consistently with experiment.
Agranat, Israel,Oded, Yaacov Netanel,Mala’bi, Tahani,Pogodin, Sergey,Cohen, Shmuel
p. 1579 - 1610
(2019/07/29)

One-Pot Catalytic Cleavage of C=S Double Bonds by Pd Catalysts at Room Temperature
The C=S double bonds in CS2 and thioketones were catalytically cleaved by Pd dimeric complexes [(N∧N)2Pd2(NO3)2](NO3)2 (N∧N, 2,2′-bipyridine, 4,4′-dimethylbipyridine or 4,4′-bis(trifluoromethyl)) at room temperature in one pot to afford CO2 and ketones, respectively, for the first time. The mechanisms were fully investigated by kinetic NMR, isotope-labeled experiments, in situ ESI-MS, and DFT calculations. The reaction is involved a hydrolytic desulfurization process to generate C=O double bonds and a trinuclear cluster, which plays a pivotal role in the catalytic cycle to regenerate the dimeric catalysts with HNO3. Furthermore, the electronic properties of catalyst ligands possess significant influence on reaction rates and kinetic parameters. At the same temperature, the reaction rate is consistent with the order of electronegativity of N∧N ligands (4,4′-bis(trifluoromethyl) > 2,2′-bipyridine > 4,4′-dimethylbipyridine). This homogeneous catalytic reaction features mild conditions, a broad substrate scope, and operational simplicity, affording insight into the mechanism of catalytic activation of carbon sulfur bonds.
Zhu, Ting,Wu, Xiaoxi,Yang, Xinzheng,Sharma, Bigyan,Li, Na,Huang, Jiaming,Wang, Wentao,Xing, Wang,Zhao, Zhenwen,Huang, Hui
supporting information
p. 9266 - 9273
(2018/08/17)

Chelation-assisted Pd-catalysed ortho-selective oxidative C-H/C-H cross-coupling of aromatic carboxylic acids with arenes and intramolecular Friedel-Crafts acylation: One-pot formation of fluorenones
Pd-Catalysed ortho-selective oxidative C-H/C-H cross-coupling of aromatic carboxylic acids with arenes and subsequent intramolecular Friedel-Crafts acylation has been accomplished for the first time through a chelation-assisted C-H activation strategy. Starting from the readily available substrates, a variety of fluorenone derivatives are obtained in one pot. The direct use of naturally occurring carboxylic acid functionalities as directing groups avoids unnecessary steps for installation and removal of an extra directing group.
Sun, Denan,Li, Bijin,Lan, Jingbo,Huang, Quan,You, Jingsong
supporting information
p. 3635 - 3638
(2016/03/05)

Aluminum oxide mediated C-F bond activation in trifluoromethylated arenes
Thermally activated γ-aluminium oxide was found to be very effective for C-F bond activation in trifluoromethylated arenes. Depending on the activation degree the respective arenes can be converted either to cyclic ketones or to the respective carboxylic acids with good to excellent yields.
Papaianina,Amsharov
p. 1505 - 1508
(2016/01/25)

PhI(OAc)2-BF3-OEt2mediated domino imine activation, intramolecular C-C bond formation and β-elimination: New approach for the synthesis of fluorenones, xanthones and phenanthridines
PhI(OAc)2-BF3-OEt2mediated domino synthesis of biologically important fluorenones, xanthones and phenanthridines has been developed. The reaction proceeds through imine activation, intramolecular C-C bond formation and β-elimination. This journal is
Sarkar, Satinath,Tadigoppula, Narender
p. 40964 - 40968
(2015/02/05)

Cross dehydrogenative coupling via base-promoted homolytic aromatic substitution (BHAS): Synthesis of fluorenones and xanthones
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
p. 928 - 931
(2013/03/28)

Synthesis of fluorenones via quaternary ammonium salt-promoted intramolecular dehydrogenative arylation of aldehydes
Biologically interesting fluorenone, xanthone and anthrone derivatives have been prepared via an intramolecular oxidative acylation process. This novel direct acylation reaction proceeded without the aid of any transition metals, acids or bases, and uses a catalytic amount of a quaternary ammonium salt in the presence of a persulfate oxidant. Initial mechanistic studies have been carried out to elucidate the reaction pathway. The Royal Society of Chemistry 2013.
Shi, Zhuangzhi,Glorius, Frank
p. 829 - 833
(2013/03/28)

Metal-free directed ortho C-H iodination: Synthesis of 2'-iodobiaryl-2- carbonitriles
Metal-free directed ortho C-H iodination of biaryl-2-carbonitriles was developed. A series of 2'-iodobiaryl-2-carbonitriles were synthesized from substituted biphenylcarbonitriles and naphthylbenzonitriles in reasonably good yields by using bis(pyridine)iodonium(I) tetrafluoroborate (IPy 2BF4, Barluenga's reagent) and HBF4· OEt2. The biaryl-2-carbonitriles are useful precursors for the synthesis of benzocyclic ketones. Metal-free directed ortho C-H iodination of biaryl-2-carbonitriles is efficiently performed in good yields by using bis(pyridine)iodonium(I) tetrafluoroborate (IPy2BF4, Barluenga's reagent) and HBF4·OEt2. Copyright
Sarkar, Satinath,Jana, Manoranjan,Narender, Tadigoppula
p. 6491 - 6495
(2013/11/06)

Novel syntheses of fluorenones via nitrile-directed palladium-catalyzed C-H and dual C-H bond activation
Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.
Wan, Jung-Chih,Huang, Jun-Min,Jhan, Yu-Huei,Hsieh, Jen-Chieh
supporting information
p. 2742 - 2745
(2013/07/19)

Pd-catalyzed double C-H bond activation of diaryl ketones for the synthesis of fluorenones
An efficient synthesis of fluorenones from diaryl ketones by Pd-catalyzed oxidative cyclization is described. A possible mechanism involving a carbonyl group assisted ortho-C-H activation and cyclometalation followed by a second C-H activation to form a six-membered palladacycle and reductive elimination is proposed.
Gandeepan, Parthasarathy,Hung, Chen-Hsun,Cheng, Chien-Hong
supporting information; experimental part
p. 9379 - 9381
(2012/09/22)

Pd-catalyzed multiple C-H functionalization to construct biologically active compounds from aryl aldoxime ethers with arenes
Functional fluorenones: Aromatic aldoxime ethers react with unactivated arenes catalyzed by palladium complexes to give biologically active fluoren-9-ones (see scheme). Multiple C-H bond activation and an oxidative cyclization are involved in the reaction.
Thirunavukkarasu, Vedhagiri S.,Cheng, Chien-Hong
supporting information; experimental part
p. 14723 - 14726
(2012/02/01)

Direct intramolecular arylation of aldehydes promoted by reaction with IPy2BF4/HBF4: Synthesis of benzocyclic ketones
(Chemical Equation Presented) Iodine helps: Aldehydes acylate arenes upon treatment at low temperature with IPy2BF4 and HBF 4. This reaction is exploited in a novel intramolecular approach to the preparation of benzocyclic ketones (see scheme). A plausible mechanistic rational is also given.
Barluenga, Jose,Trincado, Monica,Rubio, Eduardo,Gonzalez, Jose M.
p. 3140 - 3143
(2007/10/03)

Perylene derivatives formation in reaction of 3-bromobenzanthrone and 4-bromonaphthalic acid derivatives with a reduction system NiCl2 - 2,2′bipyridyl (or 1,10-phenathroline) - Zn
The reaction of 3-bromobenzanthrone and 4-bromonaphthalic acid derivatives with a reduction system NiCl2-2,2′bipyridyl (or 1,10-phenathroline)-Zn gives rise to compounds containing perylene fragment. Under similar conditions was established a possibility to transform substituted 1,1′-binaphthyls into the corresponding perylene derivatives.
Adonin,Ryabinin,Starichenko
p. 861 - 865
(2007/10/03)

Synthesis of Ketone and Alcohol Derivatives of Methylene-Bridged Polyarenes, Potentially New Classes of Active Metabolites of Carcinogenic Hydrocarbons
Methods for the syntheses of bridge ketone and alcohol derivatives of methylene-bridged polyarenes from the parent hydrocarbons are described.The polyarenes investigated include 4H-cyclopentaphenanthrene (1a), fluorene (2a), 7H-benzofluorene (3a), 4H-cyclopentachrysene (4a), 11H-benzaceanthrylene (5a), 10H-indenopyrene (6a), 11H-dibenzoaceanthrylene (7a), 4H-fluorenoanthracene (8a), and 7H-dibenzofluorene (9a).The bridge ketone derivatives are most efficiently synthesized via treatment of the parent hydrocarbons with n-butyllithium and reaction of the resulting anionic intermediate s with molecular oxygen.The direct formation of ketones rather than the expected hydroperoxides from reaction of the bridge anions with O2 presumably involves intra- or intermolecular abstraction of a proton from the benzylic site of the intermediate by the peroxy anion leading to loss of hydroxide ion with formation of a carbonyl group.Yields are generally high except in the cases of 1a and 4a; the former affords as the principal product a dimeric alcohol arising from reaction of the anion of 1a with the corresponding ketone 1b.The related bridge alcohols are readily obtained in yields of 75-95percent by reduction of the crude products from the preceding oxidations with NaBH4.
Harvey, Ronald G.,Abu-shqara, Elias,Yang, ChengXi
p. 6313 - 6317
(2007/10/02)

Studies on the Formation of Benzanthrones in Alkaline Anthraquinone Pulping
Loss of anthraquinone (AQ) in alkaline pulping is partly attributed to irreversible reactions of AQ or AQ-derived compounds with lignin fragments. 3-(4-Hydroxy-3-methoxyphenyl)benzanthracen-7-one, 3-(4-hydroxy-3,5-diemethoxyphenyl)benzanthracen-7-one and 3-(4-hydroxyphenyl)benzanthracen-7-one have been synthesized and their formation in reactions of isolated lignins has been studied. 2-(4-Hydroxy-3-methoxyphenyl)anthracene-9,10-dione (2-vanillylanthraquinone) has also been prepared.
Karhunen, Pirkko,Brunow, Goesta
p. 945 - 948
(2007/10/02)

Derivatization of Vinyl Aldehydes with Anthrone Prior to High-Performance Liquid Chromatography with Fluorometric Detection
Precolumn high-performance liquid chromatography derivatization of several vinyl aldehydes, specifically acrolein, crotonaldehyde, and methacrolein, has been studien by use of the reagent anthrone.After selective condensation of these α or β-unsaturated aldehydes to form fluorescent benzanthrone derivatives, separation of these compounds was facile on a 10-cm C-18 column.Although ultraviolet detection was possible, fluorescent detection proved more versatile and sensitive.Four liquor samples were subsequently assayed for acrolein and crotonaldehyde.Linearity for these compounds in alcoholic solutions ranged from 0.02 to at least 14 ppm with detection limits reaching down to 0.005pmm.
Miller, Blair E.,Danielson, Neil D.
p. 622 - 626
(2007/10/02)

CONVERSION OF 3-BROMOBENZANTHRONE INTO VIOLANTHRONE UNDER THE CONDITIONS OF CATALYSIS BY PALLADIUM COMPOUNDS
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Shigalevskii, V. A.,Borodina, A. V.,Kozyuberda, L. I.
p. 1413 - 1414
(2007/10/02)

Phase-Transfer Permanganate Oxidation of Unfunctionalized Benzylic Positions
The utility of potassium permanganate in a biphasic medium employing a phase-transfer catalyst is described for the selective oxidations of doubly-benzylic secondary carbons to ketones and doubly-benzylic tertiary carbons to alcohols as well as of singly-benzylic secondary alcohols to ketones.
Gannon, Sharon M.,Krause, Josef G.
p. 915 - 917
(2007/10/02)

Benzylic Oxidation with 2,3-Dichloro-5,6-dicyanobenzoquinone in Aqueous Media. A Convenient Synthesis of Aryl Ketones and Aldehydes
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Lee, Hongmee,Harvey, Ronald G.
p. 749 - 751
(2007/10/02)

Electrochemical process for the production of benzanthrone
An electrochemical process for the production of benzanthrone by reaction of anthraquinone as, starting material, with glycerol, which process comprises reducing anthraquinone, which may additionally contain electronegative substituents, at the cathode in an electrolytic cell in acid medium, and simultaneously cyclizing the reduced semiquinone form with glycerol to produce the corresponding benzanthrone. The novel process affords numerous advantages compared with chemical reduction methods.
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(2008/06/13)

CATALYTIC METHOD FOR THE SYNTHESIS OF BENZANTHRENE AND METHYL-SUBSTITUTED BENZANTHRENES
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Prostakov, N. S.,Pleshakov, V. G.,Zainul Abedin, Md.
p. 2199 - 2200
(2007/10/02)