- A one-pot construction of acridones by rhodium catalyzed reaction of N-phenyl-2-(1-sulfonyl-1H-1,2,3-triazol-4-yl)aniline
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A one-pot synthesis of N-alkyl acridone via rhodium catalyzed decomposition of N-phenyl-2-(1-sulfonyl-1H-1,2,3-triazol-4-yl)aniline and subsequent oxidative C–C bond fragmentation has been developed. 14 examples are presented and the yields range from 30% to 80%.
- Xu, Hua-Dong,Pan, Ying-Peng,Ren, Xin-Tao,Zhang, Ping,Shen, Mei-Hua
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Read Online
- 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 Acridones by Palladium-Catalyzed Buchwald-Hartwig Amination
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The Buchwald-Hartwig amination allows an efficient and convenient synthesis of biologically and pharmaceutically important acridones by formation of a six-membered ring. With the described method, a number of derivatives have been synthesized in up to 95% yield by using a variety of anilines as well as benzylic and aliphatic amines.
- Janke, Julia,Villinger, Alexander,Ehlers, Peter,Langer, Peter
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p. 817 - 820
(2019/04/25)
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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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- Photocatalytic oxidation synthesis method of acridone compound
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The invention discloses a photocatalytic oxidation synthesis method of an acridone compound. According to the method, a 9,10-dihydroacridine compound is used as a reaction substrate, 2,3-dichloro-5,6-dinitrile group-1,4-benzoquinone (DDQ) and tert-butyl nitrite (TBN) are used as catalysts, acetic acid is used as a reaction aid, oxygen is used as an oxidant, the reaction substrate reacts in a 1,2-dichloroethane solvent at normal temperature and pressure under blue light irradiation, and after the completion of the reaction, the acridone compound is obtained by separation treatment. According tothe synthesis method provided by the invention, a traditional heating reaction is replaced with an illumination reaction, thereby saving energy; no transition metal catalyst is used; and the productyield is high under optimized conditions.
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Paragraph 0047-0050
(2019/02/26)
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- Synthesis method of acridone derivative
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The application relates to a synthesis method of an acridone derivative. The synthesis method comprises the following steps: mixing a compound shown in a formula (I), a photocatalyst and a solvent, reacting under the conditions of oxygen and lighting and obtaining the acridone derivative. The synthesis method of the acridone derivative has the beneficial effects that the photocatalyst can catalyzethe compound shown in the formula (I) to carry out intramolecular hydrocarbon ammoniation reaction under the conditions of oxygen and lighting so as to synthesize the acridone derivative, and the pretreatment for the compound shown in the formula (I) is not needed; the operation is simple and convenient, and the condition is mild, the yield is high; the synthesis method conforms to the economic and environment-friendly characteristics of atoms and has high practical value for industrial preparation of the acridone derivative.
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Paragraph 0047-0049; 0116-0118; 0123-0125; 0074-0076
(2019/01/05)
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- Preparation method of acridone and derivatives thereof
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The invention discloses a preparation method of acridone and derivatives thereof. The method is characterized in that 2-halogenated diphenylamine compounds are used as a substrate, and the acridone and the derivatives thereof are prepared by means of a palladium catalyzed carbonylation reaction under a carbon monoxide atmosphere. The reaction raw materials of the method are relatively easy to obtain, and the reaction conditions are mild; this method breaks the limitation that the substrate needs to be introduced into a precursor of a carbonyl functional group in advance in the conventional preparation method; the carbon monoxide is used as a direct source of the carbonyl group, and two C-C bonds are constructed by means of the carbonylation reaction in one step, so that the method is bestin line with the concepts of atomic economy, synthetic process economy and green chemistry in organic synthesis; organic methodologies is developed, and the efficient preparation of acridone compoundsis also realized.
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Paragraph 0068; 0069; 0070; 0071; 0072
(2018/07/30)
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- Synthesis of acridones through palladium-catalyzed carbonylative of 2-bromo-diarylamines
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A facile protocol for the synthesis of acridone derivatives has been developed through palladium-catalyzed carbonylation/C–H activation sequence from 2-bromo-diarylamines in moderate to excellent yields. The reactions occurred smoothly and allowed both el
- Song, Juan,Ding, Keran,Sun, Wei,Wang, Songjiang,Sun, Haisen,Xiao, Kang,Qian, Yan,Liu, Chao
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supporting information
p. 2889 - 2892
(2018/06/25)
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- Method for construction of C-N bond for synthesis of acridone derivative by intramolecular decarboxylation coupling
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The present invention provides a method for construction of a C-N bond for synthesis of an acridone derivative by intramolecular decarboxylation coupling, the synthesis process is as follows: a formula (I) compound, anhydrous 1, 10-phenanthroline, copper acetate, palladium acetate and silver carbonate are added to solvent anhydrous DMF, and heated in O2 atmosphere to 120 to 160 DEG C for reaction for 12-16h, and after postprocessing of a reaction liquid, the acridone derivative shown as a formula (II) can be obtained; the C-N bond can be constructed in one step for synthesis of an acridone product, the method has the advantages of high efficiency, low cost and good yield, conventional reagents are used in the reaction, and the conventional reagents are low-toxicity, environmental-friendly and economic.
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Paragraph 0020; 0021; 0022; 0023; 0024; 0025
(2017/10/07)
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- Oxidative C-H bond functionalization and ring expansion with TMSCHN2: A copper(I)-catalyzed approach to dibenzoxepines and dibenzoazepines
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Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for the pharmaceutical industry and academic research. However, their syntheses are generally rather tedious, requiring several steps that involve a Wagner-Meerwein-type rearrangement under harsh conditions. Herein, we present the first copper(I)-catalyzed oxidative C-H bond functionalization and ring expansion with TMSCHN2 to yield these important derivatives in a facile and straightforward way. Cut a long story short: Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for pharmaceuticals, but their syntheses are generally rather tedious. A copper(I)-catalyzed oxidative C-H bond functionalization and ring expansion sequence with TMSCHN2 has been developed to yield these important derivatives in a facile and straightforward way.
- Stopka, Tobias,Marzo, Leyre,Zurro, Mercedes,Janich, Simon,Würthwein, Ernst-Ulrich,Daniliuc, Constantin G.,Alemán, José,Manche?o, Olga García
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supporting information
p. 5049 - 5053
(2015/04/27)
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- Ligand controlled regiodivergent C1 insertion on arynes for construction of phenanthridinone and acridone alkaloids
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A palladium-catalyzed regiodivergent C1 insertion multicomponent reaction involving aryne, CO, and 2-iodoaniline is established to construct the scaffolds of phenanthridinone and acridone alkaloids. Regioselective control is achieved under the guidance of selective ligands. The phenanthridinones are solely obtained under ligand-free condition. In comparison, application of the electron-abundant bidentate ligand dppm afforded the acridones with high efficiency. The release rate of the aryne from the precursor assists the regioselectivity of insertion as well, which was revealed through interval NMR tracking. A plausible mechanism was suggested based on the control experiments. Representative natural products and two types of natural product analogues were synthesized divergently through this tunable method. Divergent alkaloid synthesis: A multicomponent, regioselective approach for palladium-catalyzed C1 insertion is described. This reaction was applied in the divergent synthesis of phenanthridinone and acridone natural product core scaffolds.
- Feng, Minghao,Tang, Bingqing,Wang, Nengzhong,Xu, Hong-Xi,Jiang, Xuefeng
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supporting information
p. 14960 - 14964
(2016/02/05)
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- PhI(OAc)2-mediated intramolecular oxidative aryl-aldehyde C sp 2-C sp 2 bond formation: Metal-free synthesis of acridone derivatives
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A metal-free protocol for direct aryl-aldehyde Csp2-Csp 2 bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.
- Zheng, Zisheng,Dian, Longyang,Yuan, Yucheng,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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p. 7451 - 7458
(2014/09/17)
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- Synthesis of 10-aryl- and 10-(arylmethyl)acridin-9(10H)-ones via the reaction of (2-fluorophenyl)(2-halophenyl)methanones with benzenamines and arylmethanamines
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The reaction of 1-fluoro-2-lithiobenzenes, generated from 1-bromo-2-fluorobenzenes 1 and BuLi, with 2-halobenzaldehydes and subsequent oxidation of the resulting alcohols 2 afforded (2-fluorophenyl)(2-halophenyl) methanones 3, which, on treatment with ben
- Kobayashi, Kazuhiro,Nakagawa, Kazuhiro,Yuba, Shohei,Komatsu, Toshihide
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p. 389 - 396
(2013/05/09)
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- Synthesis of 10-methylacridin-9(10H)-ones through Cu-Catalyzed Intramolecular Oxidative C(sp2)-H Amination of 2-(Methylamino) benzophenones
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An efficient synthesis of a diverse set of 10-methylacridin-9(10H)-ones from 2-(methylamino)benzophenones has been developed. The reaction proceeds though Cu-catalyzed intramolecular aromatic C-H amination by using O2 as the sole oxidant to provide the desired products in moderate to good yields. In addition, 2-allylamino- and 2-(benzylamino)benzophenones as well as unprotected substrates can also undergo the C-H amination reaction to deliver the corresponding cyclization products smoothly. Preliminary mechanistic studies suggest that C-H activation is involved in a rate-limiting step. An efficient synthesis of a diverse set of 10-methylacridin-9(10H)-ones from 2-(methylamino)benzophenones has been developed. The reaction proceeds through Cu-catalyzed intramolecular aromatic C-H amination by using O2 as the oxidant. Mechanistic studies suggest that a rate-limiting C-H activation step is involved in the C-N bond-formation process.
- Huang, Jinbo,Wan, Congqing,Xu, Ming-Fang,Zhu, Qiang
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supporting information
p. 1876 - 1880
(2013/04/24)
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- N-substituted phenoxazine and acridone derivatives: Structure-activity relationships of potent P2X4 receptor antagonists
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P2X4 receptor antagonists have potential as drugs for the treatment of neuropathic pain and neurodegenerative diseases. In the present study the discovery of phenoxazine derivatives as potent P2X4 antagonists is described. N-Substituted phenoxazine and related acridone and benzoxazine derivatives were synthesized and optimized with regard to their potency to inhibit ATP-induced calcium influx in 1321N1 astrocytoma cells stably transfected with the human P2X4 receptor. In addition, species selectivity (rat, mouse, human) and receptor subtype selectivity (versus P2X1,2,3,7) were investigated. The most potent P2X4 antagonist of the present series was N-(benzyloxycarbonyl)phenoxazine (26, PSB-12054) with an IC50 of 0.189 μM and good selectivity versus the other human P2X receptor subtypes. N-(p-Methylphenylsulfonyl)phenoxazine (21, PSB-12062) was identified as a selective P2X4 antagonist that was equally potent in all three species (IC50: 0.928-1.76 μM). The compounds showed an allosteric mechanism of action. The present study represents the first structure-activity relationship analysis of P2X4 antagonists.
- Hernandez-Olmos, Victor,Abdelrahman, Aliaa,El-Tayeb, Ali,Freudendahl, Diana,Weinhausen, Stephanie,Müller, Christa E.
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supporting information
p. 9576 - 9588
(2013/01/16)
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- Metal-free TEMPO-catalyzed oxidative C-C bond formation from Csp 3-H bonds using molecular oxygen as the oxidant
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An efficient TEMPO-catalyzed oxidative C-C bond formation with two Csp 3-H bonds using molecular oxygen as the oxidant has been developed. The novel transformation provides a new strategy for the TEMPO-O2 catalysis to construct C-C bonds. The advantages of this method include: (1) relatively mild and neutral conditions; (2) simplicity and safety of operation; (3) a stoichiometric amount of dangerous oxidants, any transition metals, additives, even solvent, is not required.
- Zhang, Bo,Cui, Yuxin,Jiao, Ning
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scheme or table
p. 4498 - 4500
(2012/06/01)
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- Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones
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N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.
- Fang, Yuesi,Rogness, Donald C.,Larock, Richard C.,Shi, Feng
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p. 6262 - 6270
(2012/09/22)
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- Synthesis and evaluation of N-Benzyl-acridinone derivatives induced apoptosis in human liver cancer cell-lines
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A series of N-benzyl-9(10H)-acridinones were synthesized and tested for their antitumor activities in vitro against HepG2 cells Assay-based antiproliferative activity study using HepG2 cell lines revealed that several compounds had significant effects on cytotoxicity, among which compound 5h was found to be the most active compound with IC50 at about 1.33 μM using the MTT assay. The antitumor effect of compound 5h is believed to be due to the induction of apoptosis, which was further confirmed by Hoechst 33258 fluorescence staining, agarose gel electrophoresis and Annexin VFITC/ PI staining assay using flow cytometry analysis. Above all, compound 5h would be a potential anticancer agent which deserves further research.
- Huang, Xian-Feng,Yulan-Zhua,Zhu, Hai-Liang
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experimental part
p. 606 - 611
(2012/06/04)
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- Autoxidative carbon-carbon bond formation from carbonhydrogen bonds
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(Figure Presented) Only oxygen and acid! The oxidative coupling of xanthene and other activated benzylic compounds with carbon nucleophiles such as ketones, can be performed under ambient conditions without solvent by simply using oxygen and catalytic amounts of methanesulfonic acid. The proposed reaction mechanism involves substrate activation by formation of hydroperoxides; the method can therefore be regarded as an "autoxidative coupling reaction".
- Pinter, Aron,Sud, Abhishek,Sureshkumar, Devarajulu,Klussmann, Martin
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supporting information; experimental part
p. 5004 - 5007
(2010/09/08)
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- Synthesis and potent antileukemic activities of 10-benzyl-9(10H)-acridinones
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A novel series of 10-benzyl-9(10H)-acridinones and 1-benzyl-4-piperidones were synthesized and tested for their in vitro antitumor activities against CCRF-CEM cells. Assay-based antiproliferative activity study using CCRF-CEM cell lines revealed that the acridone group and the substitution pattern on the benzene unit had significant effect on cytotoxicity of this series of compounds, among which 10-(3,5-dimethoxy)benzyl-9(10H)-acridinone (3b) was found to be the most active compound with IC50 at about 0.7 μM. Compound 3b was also found to have antiproliferative activity against two other human leukemic cell lines K562 and HL60 using the MTT assay. The antitumor effect of 3b is believed to be due to the induction of apoptosis, which is further confirmed by PI (Propidium iodide) staining and Annexin V-FITC/PI staining assay using flow cytometry analysis.
- Gao, Chunmei,Jiang, Yuyang,Tan, Chunyan,Zu, Xuyu,Liu, Huachen,Cao, Derong
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p. 8670 - 8675
(2008/12/23)
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- Rhodium-catalyzed aryl transfer from trisubstituted aryl methanols to α,β-unsaturated carbonyl compounds
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(Chemical Equation Presented) A process of elimination: The rhodium-catalyzed arylation of α,β-unsaturated carbonyl compounds with 9-aryl-10-benzyl-9,10-dihydroacridin-9-ols 1 as arylating reagents proceeds efficiently via β-aryl elimination of the rhodium alkoxide intermediates, to give the 1,4-addition products in high yields (see scheme; Bn = benzyl, cod = cycloocta-1,5-diene).
- Nishimura, Takahiro,Katoh, Taisuke,Hayashi, Tamio
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p. 4937 - 4939
(2008/02/08)
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- Microwave-promoted N-alkylation of acridones without solvent
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N-Alkylacridones (3) were effectively synthesized in few minutes by reaction of acridone and alkyl halides with NaOH/K2CO3 absorbed on Al2O3 in the presence of TBAB under microwave irradiation without solvent.
- Wang, Cunde,Hang, Tianlong,Zhang, Hui
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p. 451 - 456
(2007/10/03)
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- The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 21. A Mild Process For The Preparation of 10-Alkyl-9-acridanones And It's Application To The Synthesis of Acridone Alkaloids
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10-Substituted-9-acridanones are readily prepared by the reaction of the corresponding isatoic anhydride with the lithium enolate of 2-cyclohexen-1-one.The initially formed product, the 1,2-dihydroacridone need not be purified but can be aromatized directly with DDQ to the desired acridone.This methodology is applicable to the synthesis of acridone natural products.Two alkaloids, 1,2,3-trimethoxy-10-methylacridone (9) and evoxanthine (10), were prepared from 4,5,6-trimethoxy-N-methylisatoic anhydride and 6-methoxy-4,5-methylenedioxy-N-methylisatoic anhydride respectively.In these trioxygenated systems, palladium-on-charcoal must be used to aromatize the penultimate intermediate.
- Coppola, Gary M.,Schuster, Herbert F.
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p. 957 - 964
(2007/10/02)
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- ETUDE COMPARATIVE DE LA REACTIVITE DES ACRIDANONES, DES AMINOACRIDINES ET DES THIOACRIDANONES VIS-A-VIS DES AGENTS D'ALKYLATION DANS LES CONDITIONS DE LA CATALYSE PAR TRANSFERT DE PHASE
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This paper describes the results obtained in the alkylation of thioacridanone under phase transfer catalysis conditions.Nine different alkylating agents have been used and in all the cases the thioether was the sole product obtained.Proton and carbon-13 n.m.r. study of the different compounds has been carried out, giving an useful criteria to differentiate thioethers and thioacridanones.The HSAB principle has been used to discuss the relative amounts of 9- and 10- substituted isomers obtained from acridanones, aminoacridines and thioacridanones using different alkylating and acylating agents.
- Galy, J. P.,Vincent, E. J.,Galy, A. M.,Barbe, J.,Elguero, J.
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p. 947 - 954
(2007/10/02)
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- A Convenient Preparation of Some N-Alkylcarbazoles and N-Alkylacridones
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N-Alkylation of aromatic compounds involving nitrogen heterocycles such as carbazole and acridone with alkyl halide in the presence of caustic solution and benzyl triethyl ammonium chloride (BTEAC) as a phase-transfer catalyst readily proceeded under mild conditions.These results show that this procedure is effective for the preparation of the title compounds in high yields.
- Nishi, Hisao,Kohno, Hisao,Kano, Toshihiro
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p. 1897 - 1898
(2007/10/02)
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