- Preparation method of phenylacetic acid type compound
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The invention discloses a preparation method of a phenylacetic acid type compound. The preparation method of the phenylacetic acid type compound I comprises the following steps that in a solvent and aCO gas phase system, a benzyl halide type compound II, pyridine-2-cobalt carboxylate, palladium acetate and alkaline neutralizers take carbonylation reaction to obtain the phenylacetic acid type compound I. A mixed catalytic system has a synergistic effect; the whole use quantity of catalysts is greatly reduced. When the mixed catalyst is used, a better catalytic effect can be achieved; the characteristics of easily obtaining the catalyst, avoiding the production safety risk of toxic three wastes and the like, reducing the reaction pressure, realizing mild reaction conditions, reducing the production risk, facilitating the production and the like are realized. The formulas are shown in description.
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Paragraph 0119; 0120; 0121
(2019/02/21)
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- Method for synthesizing o-nitrophenylacetic acid
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The invention discloses a method for synthesizing o-nitrophenylacetic acid. Absolute ethyl alcohol, Pt-MgO-CNTs, metal sodium, o-nitrotoluene, diethyl oxalate, hydrogen peroxide and H2PtCl6 are used as main raw materials, the synthesis process adopts the o-nitrotoluene and diethyl oxalate to be subjected to condensation reaction to obtain the o-nitrophenylacetic acid under the action of the catalyst Pt-MgO-CNTs, the separation method of steam distillation is replaced by vacuum distillation, the reaction time is greatly shortened, and the separation effect is significantly enhanced. The optimummaterial ratio, the temperature of oxidation reactions and the temperature and time of condensation reactions are optimized by a large number of experiments, and the yield is greatly improved.
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Paragraph 0008; 0010; 0011; 0012; 0013; 0014
(2018/11/22)
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- Synthesis method of O-nitrophenylacetic acid
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The invention discloses a synthesis method of O-nitrophenylacetic acid; anhydrous ethanol, Pt-MgO-CNTs, metallic sodium, O-nitrotoluene, diethyl oxalate, hydrogen peroxide and H2PtCl6 are used as mainraw materials; according to the synthesis process, O-nitrotoluene and diethyl oxalate are subjected to condensation reaction under the action of the catalyst Pt-MgO-CNTs to obtain O-nitrophenylaceticacid; reduced pressure distillation replaces a separation method of water steam distillation, so the reaction time is greatly shortened and the separation effect is enhanced obviously. The optimum material ratio, oxidation reaction temperature and condensation reaction temperature and time are optimized through a large number of experiments, and the yield is greatly improved.
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Paragraph 0008; 0010-0029
(2019/01/07)
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- A high-throughput screening method for determining the substrate scope of nitrilases
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Nitrile compounds are intermediates in the synthesis of pharmaceuticals such as atorvastatin. We have developed a chromogenic reagent to screen for nitrilase activity as an alternative to Nessler's reagent. It produces a semi-quantifiable blue colour and hydrolysis of 38 nitrile substrates by 23 nitrilases as cell-free extracts has been shown. This journal is
- Black, Gary W.,Brown, Nicola L.,Perry, Justin J. B.,Randall, P. David,Turnbull, Graeme,Zhang, Meng
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supporting information
p. 2660 - 2662
(2015/03/05)
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- Total synthesis of bouchardatine
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Two new, efficient and simple routes using Heck-type reaction and intramolecular cyclization were developed for the synthesis of the naturally occurring cytotoxic alkaloid 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-3- carbaldehyde (bouchardatine).
- Naik, Nilesh H.,Urmode, Tukaram D.,Sikder, Arun K.,Kusurkar, Radhika S.
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p. 1112 - 1114
(2013/09/24)
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- A novel one pot synthesis of o-nitrophenylacetic acid and unexpected p-nitrobenzoic acid by HNO3-mediated CH2 extrusion reaction of phenylacetic acid
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The HNO3-mediated CH2 extrusion reactions of phenylacetic acid lead to one pot synthesis of unexpected commercially important product 4-nitrobenzoic acid through the formation of 4-nitrophenylacetic acid and 2-nitrophenylacetic acid. Copyright
- Sohail, Muhammad,Raza, Abdul Rauf
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experimental part
p. 353 - 356
(2012/05/19)
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- Facile and chemoselective cleavage of allyl carboxylic ester utilizing NaBH4 in DMSO
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A new method for deprotection of allyl carboxylic ester has been observed by using the inexpensive reagent sodium borohydride in dimethyl sulfoxide (DMSO). Aliphatic and aromatic allyl carboxylic ester undergo deprotection smoothly. The allyl ester group can selectively deprotect better than phenol.
- Pawar, Bharati V.,Lokhande, Pradeep D.
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experimental part
p. 2445 - 2453
(2009/12/06)
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- 5-Substituted pyrido[2,3-d]pyrimidine, an inhibitor against three receptor tyrosine kinases
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NP506, the 3-{2,4-dimethyl-5-[2-oxo-5-(N′-phenylhydrazinocarbonyl)-1,2-dihydro-indol-3-ylidenemethyl]-1H-pyrrol-3-yl}-propionic acid, was designed as FGF receptor 1 inhibitor by computational study and found to be more active against endothelial proliferation of HUVEC after the rhFGF-2 stimulation than SU6668 with minimum effective dose of 10 μM. NP506 inhibited the tyrosine phosphorylation in FGF, VEGF, and PDGF receptors and the activation of extracellular signal-regulated kinase (ERK), c-Jun-N-terminal-kinase (JNK) and AKT after the rhFGF-2 stimulation. The introduction of the phenyl hydrazide motif to the position 5 of the pyrido[2,3-d]pyrimidine scaffold led to the inhibitory effect in two signaling pathways: inhibition of AKT activation in the phosphatidyl inositol 3′-kinase (PI13K)/AKT signaling pathway and the inhibition of ERK and JNK activation in MAPK pathway.
- Kammasud, Naparat,Boonyarat, Chantana,Sanphanya, Kingkan,Utsintong, Maleeruk,Tsunoda, Satoshi,Sakurai, Hiroaki,Saiki, Ikuo,André, Isabelle,Grierson, David S.,Vajragupta, Opa
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scheme or table
p. 745 - 750
(2009/09/25)
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- 8-Substituted 3,4-dihydroquinolinones as a novel scaffold for atypical antipsychotic activity
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Several new, potent dopamine subtype 2 (DA D2) active compounds with serotonin subtype 2A (5-HT2A) pharmacology are presented. 8-Substituted 3,4-dihydroquinolinones, tetrahydroquinolines, and N-acyl tetrahydroquinolines were evaluated in primary assays. Subtle changes on this novel scaffold translated to large changes in potency and selectivity in vitro. These compounds show promise as novel atypical antipsychotics for the treatment of schizophrenia.
- Singer, Jamie M.,Barr, Bridget M.,Coughenour, Linda L.,Gregory, Tracy F.,Walters, Michael A.
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p. 4560 - 4563
(2007/10/03)
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- Nitric acid in the presence of P2O5 supported on silica gel - A useful reagent for nitration of aromatic compounds under solvent-free conditions
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A variety of aromatic compounds are nitrated to parent nitro aromatic compounds under solvent-free conditions using 65% nitric acid in the presence of P2O5 supported on silica gel is described. This methodology is useful for nitration of activated and deactivated aromatic rings.
- Hajipour, Abdol Reza,Ruoho, Arnold E.
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p. 8307 - 8310
(2007/10/03)
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- A fast and mild method for nitration of aromatic rings
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The use of benzyltriphenylphosphonium nitrate (PhCH2Ph 3P+NO3-) (BTPPN) as a useful reagent for nitration aromatic compounds in the presence of methanesulfonic anhydride under solvent-free conditions is described. This methodology is useful for nitration of activated aromatic rings.
- Hajipour, Abdol R.,Ruoho, Arnold E.
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p. 221 - 226
(2007/10/03)
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- Photopatternable molecular circuitry
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Bistable molecules are provided with at least one photosensitive functional group. As thus constituted, the bistable molecules are photopatternable, thereby allowing fabrication of micrometer-scale and nanometer-scale circuits in discrete areas without relying on a top conductor as a mask. The bistable molecules may comprise molecules that undergo redox reactions, such as rotaxanes and catenanes, or may comprise molecules that undergo an electric-field-induced band gap change that causes the molecules, or a portion thereof, to rotate, bend, twist, or otherwise change from a substantially fully conjugated state to a less conjugated state. The change in states in the latter case results in a change in electrical conductivity.
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Page 9; 18-19; 25-26
(2008/06/13)
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- Experiments on the Chaperon effect in the nitration of aromatics
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A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in α- position and a dilute of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced ortho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results were compared with the corresponding classical nitration in H2SO4.
- Strazzolini, Paolo,Giumanini, Angelo G.,Runcio, Antonio,Scuccato, Massimo
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p. 952 - 958
(2007/10/03)
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- Protecting Groups that can be Removed through Photochemical Electron Transfer: Mechanistic and Product Studies on Photosensitized Release of Carboxylates from Phenacyl Esters
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Photolysis of electron-donating photosensitizers in the presence of various phenacyl esters (PhCOCH2-OCOR) results in C-O bond scission leading to the formation of acetophenone (PhCOCH3) and the corresponding carboxylic acid (RCO2H). Preparative experiments showed that the carboxylic acids are generated in high or quantitative isolated yields. It is argued that this reaction is initiated by a photoinduced electron transfer from the excited state sensitizer to the phenacyl ester. The latter process forms the anion radical of the phenacyl ester which in turn undergoes rapid C-O bond scission leading to the phenacyl radical and the corresponding carboxylate anion. This mechanism is supported by the following observations. (1) The phenacyl esters quench fluorescence from the sensitizers. (2) Analysis of the redox potentials of the sensitizer excited states and the substrates shows that the proposed electron transfer step is exergonic by 15-20 kcal/mol. (3) The byproducts are indicative of the proposed ion radical intermediates. In particular N-methylaniline is detected when N4Y-dimethylaniline is used as a sensitizer. (4) Competing processes are observed in phenacyl esters whose acid components are themselves labile to single-electron transfer. For example, phenacyl 4-bromophenylacetate showed bromide elimination in competition with deprotection.
- Banerjee, Anamitro,Falvey, Daniel E.
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p. 6245 - 6251
(2007/10/03)
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- Orientation Effect of Side Chain Substituents in Aromatic Substitution. Induced Ortho Nitration
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The presence of a free carboxyl or ester function on the α-carbon of toluene induces the nitration of the phenyl ring in the ortho position at or above the statistical value (chaperon effect), when pure HNO3 is used in CH2Cl2 solution.This is at variance with the results of classical nitration in H2SO4, where p-nitration predominates by far and m-nitration occurs at a remarkable extent.The new finding is explained in terms of precomplex formation.
- Strazzolini, Paolo,Verardo, Giancarlo,Gorassini, Fausto,Giumanini, Angelo G.
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p. 1155 - 1161
(2007/10/02)
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- Electrophilic Aromatic Substitution with N-Methoxy-N-acylnitrenium Ions Generated from N-Chloro-N-methoxyamides: Syntheses of Nitrogen Heterocyclic Compounds Bearing a N-Methoxyamide Group
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N-Methoxy-N-acylnitrenium ions (II), generated by treatment of N-chloro-N-methoxyamides with silver carbonate in trifluoroacetic acid, react with arenes to give N-aryl-N-methoxyamides in good yields.In the case of the intramolecular cyclization of N-chloro-N-methoxy-2-phenylacetamides, the mode of cyclization is highly dependent on the nature of ortho or para substituent groups.Nitrenium ions II can primarily attack three positions (C-1, C-2, and C-6) of a phenyl ring.Normally II attack C-6.On the other hand, when the ortho position was occupied with a substituent group, II attacked both C-2 and C-6, in the former case followed by a 1,2-substituent migration, which was proved by a deuterium labeling experiment.Especially, when a methoxy group is substituted on ortho or para position, II attack C-1 due to the effect of the electron-releasing methoxy group to give spiro dienone compounds 39.A general discussion of the utility and mechanistic details of these reactions is presented.
- Kawase, Masami,Kitamura, Takahiro,Kikugawa, Yasuo
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p. 3394 - 3403
(2007/10/02)
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- SYNTHETIC METHODS. PART 23. REARRANGEMENT OF SOME HYDROXAMIC ACIDS INTO AMIDES. A SELF-CONDENSATION LEADING TO DISPROPORTIONATION
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Pyruvic acids have been shown to react with p-nitroso-N,N-dimethylaniline (1) to produce p-dimethyl-aminoacetanilides (3) via the corresponding hydroxamic acids (4).Three such intermediates (4a, c, d) have been isolated and their structure proved by n.m.r. and mass spectroscopy and elemental analysis.Solutions of the hydroxamic acids (4) have been shown to undergo concentration-dependent self-condensation and disproportionation leading to the amides (3) and acids (5).Rational pathways for these transformations are discussed.Spectral correlations permit differentiation between the amides (3) and the corresponding hydroxamic acids (4).
- Hassner, Alfred,Ruse, Margareta,Gottlieb, Hugo E.,Cojocaru, Miriam
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p. 733 - 738
(2007/10/02)
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