- Palladium-catalyzed direct addition of 2-Aminobenzonitriles to sodium arylsulfinates: Synthesis of o-Aminobenzophenones
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The first example of the palladium-catalyzed synthesis of o-Aminobenzophenones in moderate to excellent yields via a direct addition of sodium arylsulfinates to unprotected 2-Aminobenzonitriles was reported. A plausible mechanism for the formation of o-Aminobenzophenones involving desulfination and addition reactions was proposed. The utility of this transformation was demonstrated by its compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of o-Aminobenzophenones.
- Chen, Jiuxi,Li, Jianjun,Su, Weike
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- Design, synthesis, crystal structures, and photophysical properties of tetraphenylethene-based quinoline derivatives
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The incorporation of aggregation-induced emission (AIE) luminogens provides a molecule with enhanced fluorescent emission in the solid state. A representative AIEgen compound is tetraphenylethene (TPE). A series of new conjugates of quinolone derivatives with TPE units (1a - 1f) was synthesized and characterized. The influence on the photophysics of 1a - 1e with a variety of functional groups was investigated systematically by spectroscopic methods and simulated by density-functional theory calculations. A centrosymmetric compound donor-acceptor-donor-type compound 1f with two TPE moieties proved to be the most promising multifunctional material, it exhibited tri-colored (489–569 nm) fluorescence characteristics in tetrahydrofuran-H2O solution with a different water fraction and intense tri-colored solvatochromic (blue, green, and yellow) behaviors. These compounds could be applied as promising acid-base gas probe based on their evident color switch. Compounds 1a - 1f showed the advantage of being a potential piezochromic material.
- Zhu, Xiaolin,Wang, Danfeng,Huang, Hai,Zhang, Xueqiong,Wang, Shifan,Liu, Rui,Zhu, Hongjun
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- Benzene type liquid crystal compound and preparation method thereof
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The invention relates to the technical field of liquid crystal compounds, in particular to a benzene liquid crystal compound and a preparation method thereof, wherein the benzene type liquid crystal compound is N. 4 , N4 , N4 ’ , N4 ’ - (9, 9 - Diphenyl - 9H - fluorene -3 - yl) -2 - methyl - [1, 1 ’ - biphenyl] -4, 4 ’ - diamine, the preparation method of the benzene type liquid crystal compound is that 2 - nitrobenzoic acid is used as a starting material to react with oxalyl chloride to obtain 2 - nitrobenzoyl chloride. The reaction was again reacted with bromobenzene to give (4 - bromophenyl) (2 - nitrophenyl) methyl ketone. The reduction reaction is followed by obtaining (4 - bromophenyl) (2 - aminophenyl) methyl ketone. The 3 - bromo - 9H - fluorene -9 - ketone is obtained by using sulfuric acid and sodium nitrite as a catalyst. The Grignard reagent of bromobenzene is reacted again to obtain 3 - bromo -9, 9 - diphenyl - 9H - fluorene. Reaction with cuprous iodide gives 3 - iodine -9, 9 - diphenyl - 9H - fluorene. 2 - Methyl - [1, 1 ’ - biphenyl] -4, 4 ’ - diamine was prepared, and then reacted with 3 - iodine -9, 9 - diphenyl - 9H - fluorene to obtain the benzene-based liquid crystal compound of the present invention. The invention can be applied to preparation of liquid crystal mixtures, liquid crystal display device materials or electro-optical display device materials.
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Paragraph 0100; 0111-0114; 0142; 0152-0154
(2021/09/29)
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- Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks
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Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.
- Li, Liping,Gao, Hui,Sun, Ming,Zhou, Zhi,Yi, Wei
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supporting information
p. 5473 - 5478
(2020/07/14)
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- One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization
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A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments.
- Li, Quanzhe,Liu, Jiaxin,Wei, Yin,Shi, Min
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p. 2438 - 2455
(2020/01/31)
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- Gold-catalyzed cyclization of 1-(2′-Azidoaryl) propynols: Synthesis of polysubstituted 4-quinolones
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An unprecedented gold-catalyzed procedure for the synthesis of polysubstituted 4-quinolones from 1-(2′-Azidoaryl) propynols is described. The reaction undergoes an intramolecular nucleophilic attack of the azide group to the Au-Activated triple bonds in a 6-endo-dig manner and subsequent gold-Assisted expulsion of N2 to furnish an α-imino gold carbene intermediate, which triggers a 1,2-carbon migration and finally is converted to 2,3-disubstituted 4-quinolone.
- Wu, Xiang,Zheng, Lang-Lang,Zhao, Li-Ping,Zhu, Cheng-Feng,Li, You-Gui
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supporting information
p. 14769 - 14772
(2019/12/24)
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- Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
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An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.
- Ruzi, Rehanguli,Ma, Junyang,Yuan, Xiang-Ai,Wang, Wenliang,Wang, Shanshan,Zhang, Muliang,Dai, Jie,Xie, Jin,Zhu, Chengjian
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p. 12724 - 12729
(2019/11/05)
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- Palladium-Catalyzed Cascade Reductive and Carbonylative Cyclization of Ortho-Iodo-Tethered Methylenecyclopropanes (MCPs) Using N-Formylsaccharin as CO Source
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A palladium-catalyzed reductive and carbonylative cyclization of ortho-iodo-tethered methylenecyclopropanes (MCPs) using N-formylsaccharin as CO source has been developed, affording the desired indanone derivatives in moderate to good yields with high regio- and stereoselectivity and good functional group compatibility.
- Fan, Xing,Shi, Min,Wei, Yin
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p. 5677 - 5683
(2019/11/16)
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- Method for catalytically synthesizing Bronuck intermediate 2-amino-4'-bromo-benzophenone
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The invention relates to a method for catalytically synthesizing a Bronuck intermediate 2-amino-4'-bromo-benzophenone. The method comprises the following steps: catalytic promotion is carried out by using Bronsted acid in the presence of a nickel catalyst, and o-aminobenzonitrile reacts with p-bromophenylboronic acid in a mixed solvent, so that the 2-amino-4'-bromo-benzophenone is obtained. According to the method, through comprehensive selection of a suitable reaction system, a plurality of defects existing in the prior art are overcome, and particularly serious defects that products cannot be obtained are overcome, so that easy-to-obtain raw materials are provided for synthesis of Bronuck, and therefore, the method has remarkable economic values and application potentials in the field of medicine synthesis of the Bronuck.
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Paragraph 0052; 0054; 0055; 0056; 0057; 0058-0089
(2019/04/26)
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- Catalyst-free geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes via a Wagner-Meerwein rearrangement
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A catalyst-free intramolecular geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes has been developed. The reaction proceeded through two SET processes with Selectfluor to give a fluorinated cyclopropylcarbinyl cation and a further Wagner-Meerwein rearrangement to generate a cyclobutyl carbocation, which undergoes intramolecular nucleophilic capture by amide to forge fluorinated cyclobuta[b]indoline derivatives. A polycyclic multi-fluorinated byproduct was also formed through a Ritter-type reaction in some cases.
- Fan, Xing,Wang, Qiang,Wei, Yin,Shi, Min
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p. 10503 - 10506
(2018/09/21)
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- Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles
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An intramolecular cascade amination/cyclization/aromatization reaction of functionalized alkylidenecyclopropanes has been developed in the presence of silver acetate, affording a variety of [2,3-c]dihydrocarbazoles and [2,3-c]carbazoles in moderate to excellent yields. The mechanistic investigations revealed that this cascade reaction proceeds through a radical initiated process. Moreover, further transformations for the synthesis of eustifoline-D and an OLED exhibit a potential synthetic utility of this method.
- Fan, Xing,Yu, Liu-Zhu,Wei, Yin,Shi, Min
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p. 4476 - 4479
(2017/09/11)
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- Synthesis of 3-Sulfonylamino Quinolines from 1-(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion
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We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C - C bond migration. (Chemical Equation Presented).
- Kumar, Yalla Kiran,Kumar, Gadi Ranjith,Reddy, Thota Jagadeshwar,Sridhar, Balasubramanian,Reddy, Maddi Sridhar
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supporting information
p. 2226 - 2229
(2015/05/13)
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- Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: Synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles
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A palladium-catalyzed direct addition of arylboronic acids to unprotected 2-aminobenzonitriles has been developed, leading to a wide range of 2-aminobenzophenones with moderate to excellent yields. The transformation has broad scope and high functional group tolerance. Moreover, 2-oxoindoline-7-carbonitrile and indole-7-carbonitrile were applicable to this process for the construction of 7-benzoyl-2-oxoindolines and 7-benzoylindoles, respectively. Among the compounds examined, compound 4e possessed the most potent anticancer activity against H446 and HGC-27 in vitro, with IC50 values of 0.02 μmol L-1 and 0.09 μmol L-1, respectively, while compound 4a showed the best potent anticancer activity against SGC-7901 with an IC50 value of 0.01 μmol L-1. Furthermore, we also performed in silico molecular docking calculations to investigate the interaction mode and binding affinity between the examined compounds and their tubulin target. This journal is
- Chen, Jiuxi,Ye, Leping,Su, Weike
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supporting information
p. 8204 - 8211
(2015/01/08)
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- Ru(ii)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides
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Ru(ii)-catalyzed intermolecular ortho-C-H amidation of weakly coordinating aromatic ketones with sulfonyl azides is reported. The developed reaction protocol can be extended to various substituted aromatic ketones to afford a wide range of desired C-N bond formation products in good yields.
- Bhanuchandra,Ramu Yadav,Rit, Raja K.,Rao Kuram, Malleswara,Sahoo, Akhila K.
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supporting information
p. 5225 - 5227
(2013/06/27)
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- Blue-light-emitting multifunctional triphenylamine-centered starburst quinolines: Synthesis, electrochemical and photophysical properties
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A series of triphenylamine-centered starburst quinolines (1a-1g) have been synthesized by Friedlaender condensation of the 4,4′,4′′- triacetyltriphenylamine (2) and 2-aminophenyl ketones (3a-3g) in the presence of catalytic sulfuric acid and characterized well. They are thermally robust with high glass transition temperatures (above 176.4 °C) and decomposition temperatures (above 406 °C). These compounds emit blue fluorescence with λEmmax ranging from 433 to 446 nm in dilute toluene solution and 461 to 502 nm in the solid-state and have a relatively high efficiency (Φu = 0.98-0.57). 1a-1g have estimated ionization potentials (IP) of 4.54 to 6.45 eV which are significantly near or higher than those of well-known electron transport materials (ETMs), including tris(8- hydroxyquinoline)aluminium (Alq3) (IP = 5.7-5.9 eV), and previously reported oligoquinolines (IP = 5.53-5.81 eV). Quantum chemical calculations using DFT B3LYP/6-31G* showed the highest occupied molecular orbital (HOMO) of -5.05 to -4.81 eV, which is close to the work function of indium tin oxide (ITO). These results demonstrate the potential of 1a-1g as hole-transporting/light-emitting/electron-transport materials and the host-materials of a dopant for hole-injecting for applications in organic light-emitting devices.
- Jiang, Peng,Zhao, Dong-Dong,Yang, Xiao-Li,Zhu, Xiao-Lin,Chang, Jin,Zhu, Hong-Jun
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supporting information; experimental part
p. 4704 - 4711
(2012/08/08)
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- Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity
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A novel metal-free intramolecular oxidative decarboxylative coupling of primary α-amino acids with 2-aminobenzoketones under mild and neutral conditions was developed. Different quinazolines can be selectively obtained by various oxidants.
- Yan, Yizhe,Wang, Zhiyong
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supporting information; experimental part
p. 9513 - 9515
(2011/10/01)
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- A rapid and efficient access to diaryldibenzo[b,f][1,5]diazocines
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2-Benzoylbenzoyl azides undergo facile cyclization under acidic conditions to give substituted dibenzo[b,f][1,5]-diazocines in good yields. This approach shortens the synthetic steps toward these compounds as compared with conventional methods. The mechanism of the diazocine synthesis is assumed to proceed by an unprecedented intermolecular [2 + 2] cyclization.
- Wang, Xiao,Li, Jianzhong,Zhao, Na,Wan, Xiaobo
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p. 709 - 711
(2011/04/24)
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- A simple and efficient approach to the synthesis of 2-phenylquinazolines via sp3 C-H functionalization
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(Figure presented) A facile and novel approach to the synthesis of 2-phenylquinazolines was developed via a tandem reaction following sp 3 C-H functionalization. Twenty-five examples of 2-phenylquinazolines were obtained from easily available 2-aminobenzophenones and benzylic amines with good to excellent yields.
- Zhang, Jintang,Zhu, Dapeng,Yu, Chenmin,Wan, Changfeng,Wang, Zhiyong
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supporting information; experimental part
p. 2841 - 2843
(2010/09/04)
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- A novel and efficient methodology for the construction of quinazolines based on supported copper oxide nanoparticles
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A series of quinazolines were synthesized from 2-aminobenzophenones and benzylic amines in good to excellent yields by employing a new heterogeneous catalyst based on the copper oxide nanoparticles supported on kaolin.
- Zhang, Jintang,Yu, Chenmin,Wang, Sujing,Wan, Changfeng,Wang, Zhiyong
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supporting information; experimental part
p. 5244 - 5246
(2010/09/05)
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- A practical, metal-free synthesis of 1H-Lndazoles
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The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0-23 °C and is amenable to scale-up. The synthesis of 1 H-indazoles under these conditions is extremely mild compared with previous synthetic approaches and affords the desired compounds in good to excellent yields.
- Counceller, Carla M.,Eichman, Chad C.,Wray, Brertda C.,Stambuli, James P.
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supporting information; experimental part
p. 1021 - 1023
(2009/04/07)
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- Sulfonyl-containing 2,3-diarylindole compounds, methods for making same, and methods of use thereof
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The present invention relates to sulfonyl-containing 2,3-diarylindole, especially to new compounds of general Formula, to a preparation method for their preparation, to pharmaceutical compositions containing said compound, and to the medical use thereof in the treatment of diseases relating to the inhibition of cyclooxygenase-2 (COX-2).
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Page/Page column 15
(2010/02/06)
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- Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: A new series of selective COX-2 inhibitors
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A new series of substituted 2-sulfonyphenyl-3-phenyl-indole derivatives were synthesized and evaluated for their ability to inhibit COX-2 and COX-1enzymes. Most of the compounds synthesized were found to be highly potent and selective inhibitors of COX-2. This work led to the discovery of 2-aminosulfonylphenyl-3-phenyl-indole 5a which possesses higher activity and selectivity for COX-2 than Celecoxib both in vitro and in vivo.
- Hu, Wenhui,Guo, Zongru,Chu, Fengming,Bai, Aiping,Yi, Xiang,Cheng, Guifang,Li, Jing
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p. 1153 - 1160
(2007/10/03)
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- An In-depth Study of the Azidobenzophenone-Anthranil-Acridone Transformation
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The title transformation, particularly the conversion of anthranils into acridones, is shown to be critically sensitive to temperature, solvent, substituent, and metal catalysts.Thus the conversion of 3-(p-tolyl)anthranil into an acridone gives a ratio of 2-and 3-methyl derivatives varying from 0.6:1 to 4.7:1 with changing temperature and solvent.In other similar thermolyses, solvents (e.g. 1,2,4-trichlorobenzene) were incorporated into the product and traces of metals and their derivatives had a dramatic effect on the rate and course of the reaction.The most effective catalysts were iron powder and aluminium acetylacetonate. 3-(2,6-Disubstituted phenyl)anthranils gave acridones in which the substituents were either lost or rearranged onto N or C, the last cases involving sequential -sigmatropic shifts. 3-Thienylanthranils gave related thienoquinolones on thermolysis; again the reaction were very sensitive to catalysis.Blocked thienylanthranils also gave rearrangement products, but the non-aromatic intermediates could be isolated.
- Hawkins, David G.,Meth-Cohn, Otto
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p. 2077 - 2087
(2007/10/02)
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