- Studies on some glitazones having pyridine as the linker unit
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Molecular modeling on various well-known glitazones carrying a pyridine ring instead of benzene ring as the middle linker unit showed conformational rigidity as compared to their parent molecules. Blocking the lone pair of electrons on the pyridine N, made them flexible once again. A few representatives of these analogues were synthesized and their efficacy as PPARγ agonists evaluated.
- Ramachandran, Uma,Mital, Alka,Bharatam, Prasad V.,Khanna, Smriti,Rao, Poduri Rama,Srinivasan, Krishnamoorthy,Kumar, Rakesh,Singh Chawla, Harmander Pal,Kaul, Chaman Lal,Raichur, Suryaprakash,Chakrabarti, Ranjan
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Read Online
- Deaminative chlorination of aminoheterocycles
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Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]
- Cornella, Josep,Faber, Teresa,Gómez-Palomino, Alejandro,Ghiazza, Clément
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- Preparation method of 2-chloro-5-cyano nitrogen-containing six-membered heterocyclic compound
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The invention provides a preparation method of a 2-chloro-5-cyano nitrogen-containing six-membered heterocyclic compound. The method comprises the following steps: using a 2-hydroxy-5-bromine nitrogen-containing six-membered heterocyclic compound as a raw material, under existence of a catalyst, in atmosphere of carbon monoxide gas, using methanol as a solvent, and performing a coupling reaction to obtain a methyl 2-hydroxyl nitrogen-containing six-membered heterocyclic ring-5-carboxylate, and sequentially performing an aminolysis reaction, a chlorination reaction with phosphorus oxychloride,and an oxidation reaction to obtain the 2-chloro-5-cyano nitrogen-containing six-membered heterocyclic compound. The preparation method has the advantages of short route and easily available raw material, a post-processing method is simple, no column chromatography is required after each reaction, the reaction product can be purified only by washing and extraction of a solvent, amplification is realized, industrial production is carried out, the method accords with environmental protection requirements, and has important value for actual production.
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Paragraph 0069; 0070; 0071; 0074
(2019/01/08)
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- A method for preparing of the benzonitrile derivatives
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The invention discloses a preparation method of a cyanobenzene derivative. The cyanobenzene derivative is prepared by taking phenylacetic acid or the derivative thereof as well as urea as raw materials, copper salt as a catalyst and oxygen as an oxidizing agent. According to the preparation method disclosed by the invention, by adopting copper salt as the catalyst and oxygen as the oxidizing agent without an extra cocatalyst, the raw materials phenylacetic acid or the derivative thereof are easy to purchase in the market, low in cost and various in type, and urea as the source of cyanogen is low in toxicity, low in price, mild in reaction condition and environmentally friendly, and has a good functional group compatibility.
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Paragraph 0021; 0022; 0023; 0054; 0058; 0059; 0060
(2016/10/17)
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- Cu-Catalyzed Cyanation of Arylboronic Acids with Acetonitrile: A Dual Role of TEMPO
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The cyanation of arylboronic acids by using acetonitrile as the "CN" source has been achieved under a Cu(cat.)/TEMPO system (TEMPO=2,2,6,6-tetramethylpiperidine N-oxide). The broad substrate scope includes a variety of electron-rich and electron-poor arylboronic acids, which react well to give the cyanated products in high to excellent yields. Mechanistic studies reveal that TEMPO-CH2CN, generated in situ, is an active cyanating reagent, and shows high reactivity for the formation of the CN- moiety. Moreover, TEMPO acts as a cheap oxidant to enable the reaction to be catalytic in copper. The cyanation of arylboronic acids by using acetonitrile as the "CN" source has been achieved under a Cu(cat.)/TEMPO system. Electron-rich and electron-poor arylboronic acids react well to give the cyanated products in high to excellent yields. Mechanistic studies reveal that TEMPO-CH2CN, generated in situ, is an active cyanating reagent. Moreover, TEMPO, a cheap oxidant, enables the reaction to be catalytic in copper (see scheme; TEMPO=2,2,6,6-tetramethylpiperidine N-oxide).
- Zhu, Yamin,Li, Linyi,Shen, Zengming
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supporting information
p. 13246 - 13252
(2015/09/15)
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- Copper-catalyzed decarboxylative C≡N triple bond formation: Direct synthesis of benzonitriles from phenylacetic acids under O2 atmosphere
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A copper-catalyzed reaction of phenylacetic acids with urea was found to afford benzonitriles under an oxygen atmosphere. This reaction proceeds smoothly by a sequence of decarboxylation, dioxygen activation, C-H bond functionalization, and nitrile formation with urea as the nitrogen source. Molecular oxygen was found to play a crucial role in this transformation. This reaction represents a novel protocol for the formation of benzonitriles in an environmental friendly way and with good functional group tolerability.
- Feng, Qiang,Song, Qiuling
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supporting information
p. 1697 - 1702
(2014/06/09)
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- INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL
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The present invention provides compounds of Formula (I) and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir 1.1) channel. The compounds act as diuretics and natriuretics and are valuable pharmaceutically active compounds for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension and conditions resulting from excessive salt and water retention.
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Page/Page column 33; 34
(2013/05/21)
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- PCC-Promoted dehydration of aldoximes: A convenient access to aromatic, heteroaromatic, and aliphatic nitriles
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A simple and convenient procedure for the synthesis of nitriles by dehydration of aldoximes using a PCC (pyridiniumchlorochromate) has been developed. A variety of aromatic, heteroaromatic, and aliphatic aldoximes are converted. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the full spectral details.
- Chandrappa,Prasanna,Vinaya,Prasanna,Rangappa
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p. 2756 - 2762
(2013/08/23)
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- A novel and convenient synthesis of benzonitriles: Electrophilic cyanation of aryl and heteroaryl bromides
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N-Cyano-N-phenyl-p-methylbenzenesulfonamide has been used as a more benign electrophilic cyanation reagent for the synthesis of various benzonitriles from (hetero)aryl bromides via formation of Grignard reagents. Electronically different and sterically demanding aryl bromides including functionalized substrates and heteroaryl bromides are successfully cyanated in good to excellent yields. The efficiency of the present methodology is shown by the expeditious syntheses of interesting pharmaceutical intermediates. Notably, chemoselective monocyanation of dibromoarenes is also achieved. Copyright
- Anbarasan, Pazhamalai,Neumann, Helfried,Beller, Matthias
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supporting information; experimental part
p. 4217 - 4222
(2011/05/06)
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- Propylphosphonic anhydride (T3P): A remarkably efficient reagent for the one-pot transformation of aromatic, heteroaromatic, and aliphatic aldehydes to nitriles
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Propylphosphonic anhydride has been demonstrated to be an efficient reagent for the transformation of aromatic, heteroaromatic, and aliphatic aldehydes to respective nitriles in excellent yields. This procedure offers simple and one-pot access to nitriles and highlights the synthetic utility of T3P as a versatile reagent in organic chemistry. Georg Thieme Verlag Stuttgart - New York.
- Augustine, John Kallikat,Atta, Rajendra Nath,Ramappa, Balakrishna Kolathur,Boodappa, Chandrakantha
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experimental part
p. 3378 - 3382
(2010/03/03)
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- BICYCLIC TRIAZOLONE DERIVATIVES AND HERBICIDES CONTAINING THE SAME
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The present invention provides a bicyclic triazolone derivative represented by the formula:J-Ar [wherein, J is and Ar is ], which has excellent selective weeding activity and weed killer containing the said bicyclic triazolone derivative.
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- Practical synthesis of (6-chloro-3-pyridyl)methylamine by highly selective hydrogenation of 6-chloro-3-pyridinecarbonitrile with improved Raney nickel catalyst
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A practical synthesis of (6-chloro-3-pyridyl)methylamine (1), one of the key intermediates of neo-nicotinoid insecticides, by a highly selective hydrogenation of 6-chloro-3-pyridinecarbonitrile (4) is described. The use of an improved Raney nickel catalyst, prepared from an alloy of low nickel content (Ni 38%, A1 62%) and subjected to heat treatment in water (98 °C, 2 h) after leaching of aluminum, was highly effective for the selective hydrogenation of 4. The hydrogenation of 4 using this catalyst was carried out in EtOH-H2O [6:1 (v/v)] and NH3 at 50 °C and 1.2-1.4 kg cm-2 hydrogen pressure to give 1 in 86% yield and 3-pyridylmethylamine, a dechlorinated by-product, in 2% yield.
- Tanaka, Ken,Nagasawa, Minoru,Sakamura, Hideki
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p. 1227 - 1231
(2007/10/03)
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- Process for production of cyanopyridine
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The present invention provides a process for producing a cyanopyridine represented by general formula (3) STR1 (wherein R is a hydrogen atom or a halogen atom; X1 and X2 are each a hydrogen atom or a halogen atom with a proviso that at least either of X1 and X2 is a halogen atom; n is an integer of 1 or 2), which process comprises reacting an ammonium halide with a trichloromethylpyridine represented by general formula (1) STR2 (wherein R, X1, X2 and n have the same definitions as given above) in the presence of a metal compound represented by general formula (2) (wherein M is a copper atom or a zinc atom; X is a halogen atom or an oxygen atom; m is an integer of 2 or 1).
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- Process for the preparation of 2-halogeno-pyridine derivatives
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A process for the preparation of a 2-halogeno-pyridine of the formula STR1 in which X represents halogen and Y represents halogen, nitro, formyl, cyano, carboxyl, carbamoyl, alkyl, halogenoalkyl, alkoxyalkyl, dialkoxyalkyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, which comprises in a first stage reacting a pyridine 1-oxide of the formula STR2 with an organic nitrogen base A and an electrophilic compound, optionally in the presence of a diluent, to produce a compound of the formula STR3 in which A represents the radical of an organic nitrogen base, and Z- represents an anion formed from an electrophilic compound, optionally isolating and optionally purifying the compound of the formula (III).
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- 4-ARYL- AND 4-ARYLTHIO-5-HYDROXY-2(5H)-FURANONES AS INHIBITORS OF PHOSPHOLIPASE A2
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The invention provides novel 5-hydroxy-4-aryl- and 5-hy-droxy-4-(arylthio)-2(5H)-furanones of the following structure: wherein R contains from about five to about twenty carbon atoms and is defined herein; X is oxygen, sulfur, S02, NH, N(lower alkyl), N(lower acyl), aminocarbonyl, carbonyl, carbonylamino, CH2 or a carbon-carbon bond; Y is hydrogen, halogen, lower alkyl, nitro, alkylthio, perfluoroalkyl, hydroxy, or lower alkoxy(C1-C8); Z is sulfur or a carbon-carbon bond; and Q is H, an alkyl of from 1-20 carbon atoms, COR', COOR', CONHR', PO(OR')2, PO(OR')R" wherein R' and R" are independently selected from the group consisting of H, an alkyl of from 1-20 carbon atoms, phenyl, and substituted phenyl and prodrugs thereof and pharmaceutically acceptable salts thereof. Pharmaceutical compositions comprising these compounds, methods of using these compounds as inhibitors of inflammation and for treating other diseases characterized by the overproduction of arachidonic acid metabolites, intermediates and methods of preparing these compounds are also provided.
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- Process for the preparation of 2-halogeno-5-cyano pyridines
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The title compounds of the formula STR1 can be prepared by reacting methylene-glutaconic acid dinitriles of the formula with hydrogen halide of the formula In these formulae, X denotes fluorine, chlorine, bromine or iodine and R1 denotes --OR2 or --N(R2, R3), in which R2 and R3, independently of one another, represent straight-chain or branched C1 -C8 -alkyl, C3 -C8 -alkenyl, C2 -C8 -alkoxyalkyl, C4 -C8 -alkoxyalkenyl, C3 -C8 -cycloalkyl, C6 -C12 -aryl, C7 -C10 -aralkyl or a 5- to 8-membered saturated or unsaturated heterocyclic ring containing 1 or 2 heteroatoms from the group comprising N, O and S, where R2 and R3, with the N atom on which they are substituents, may also form a 5- to 8-membered ring which may contain a further heteroatom from the group comprising N, O and S.
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- Site-Selectivity in the Reaction of 3-Substituted Pyridine 1-Oxides with Phosphoryl Chloride
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Site-selectivity in the reaction of 3-substituted pyridine 1-oxide with phosphoryl chloride was investigated.When a strongly electron-withdrawing group (e.g.CN, CONRR', COOR, or NO2) was substituted at the 3-position, the reaction of 3-substituted pyridine 1-oxides with phosphoryl chloride yielded 3-substituted 2-chloropyridines as the main products.Keywords- site-selectivity; 3-substituted pyridine 1-oxide; phosphoryl chloride; 3-substituted 2-chloropyridine; chlorination
- Yamanaka, Hiroshi,Araki, Tomio,Sakamoto, Takao
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p. 2244 - 2247
(2007/10/02)
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