33252-28-7Relevant articles and documents
Studies on some glitazones having pyridine as the linker unit
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
, p. 655 - 662 (2004)
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.
Deaminative chlorination of aminoheterocycles
Cornella, Josep,Faber, Teresa,Gómez-Palomino, Alejandro,Ghiazza, Clément
, (2021/12/23)
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.]
Preparation method of 2-chloro-5-cyano nitrogen-containing six-membered heterocyclic compound
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Paragraph 0069; 0070; 0071; 0074, (2019/01/08)
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.
A method for preparing of the benzonitrile derivatives
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Paragraph 0021; 0022; 0023; 0054; 0058; 0059; 0060, (2016/10/17)
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.
Cu-Catalyzed Cyanation of Arylboronic Acids with Acetonitrile: A Dual Role of TEMPO
Zhu, Yamin,Li, Linyi,Shen, Zengming
supporting information, p. 13246 - 13252 (2015/09/15)
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).
Copper-catalyzed decarboxylative C≡N triple bond formation: Direct synthesis of benzonitriles from phenylacetic acids under O2 atmosphere
Feng, Qiang,Song, Qiuling
supporting information, p. 1697 - 1702 (2014/06/09)
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.
INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL
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, (2013/05/21)
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.
PCC-Promoted dehydration of aldoximes: A convenient access to aromatic, heteroaromatic, and aliphatic nitriles
Chandrappa,Prasanna,Vinaya,Prasanna,Rangappa
, p. 2756 - 2762 (2013/08/23)
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.
A novel and convenient synthesis of benzonitriles: Electrophilic cyanation of aryl and heteroaryl bromides
Anbarasan, Pazhamalai,Neumann, Helfried,Beller, Matthias
supporting information; experimental part, p. 4217 - 4222 (2011/05/06)
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
Propylphosphonic anhydride (T3P): A remarkably efficient reagent for the one-pot transformation of aromatic, heteroaromatic, and aliphatic aldehydes to nitriles
Augustine, John Kallikat,Atta, Rajendra Nath,Ramappa, Balakrishna Kolathur,Boodappa, Chandrakantha
experimental part, p. 3378 - 3382 (2010/03/03)
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.
