- Method for preparing aryl primary amide by adopting metal-catalyzed one-pot method
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The invention discloses a method for synthesizing aryl primary amide by adopting a metal-catalyzed one-pot method. The method comprises the steps of: taking aryl bromidess as raw materials, allowing the aryl bromidess to react with a cyanide source under the action of a palladium catalyst, substituting bromine on an aromatic ring with cyano to obtain cyano aromatic hydrocarbon, directly adding anaqueous solution of alkali into the reaction solution without aftertreatment, and carrying out hydrolysis reaction to obtain aryl primary amide. Compared with the prior art, the method for preparing aryl primary amide from the aryl bromides has the advantages of the short synthesis route, fewer reaction steps, simple operation, mild conditions, the high conversion rate, low toxicity and industrialproduction potential.
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Paragraph 0035; 0036
(2020/04/06)
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- A 3 - substituted - 2 - cyano pyridine compound of preparation method
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The present invention discloses a 3-substituted-2-cyanopyridine compound preparation method, which comprises: (1) mixing a solution of 3-substituted pyridine-N-oxide represented by a formula I and an acyl halide compound, and reacting to obtain a reactant; and (2) mixing the reactant I and a cyanide aqueous solution to obtain the 3-substituted-2-cyanopyridine compound represented by a formula II, wherein R is selected from methyl, halogen, hydroxy, cyano, 2-hydroxyethyl, methoxy, and 1-cyanomethyl.
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Paragraph 0094; 0097; 0100; 0103; 0106; 0107-0109
(2017/09/02)
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- A Bifunctional Reagent Designed for the Mild, Nucleophilic Functionalization of Pyridines
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Herein is reported the design and application of a reagent for the direct functionalization of pyridines. These reactions occur under mild conditions and exhibit broad functional group tolerance, enabling the late-stage functionalization of drug-like molecules. The reagent can be easily prepared on large scale from inexpensive reagents, and reacts in the title reaction with acetonitrile, sodium chloride, and sodium methanesulfonate as the sole byproducts. Although this Communication focuses primarily on reactions with cyanide as nucleophile, preliminary experiments with other nucleophiles foreshadow the broad reaching synthetic utility of this approach.
- Fier, Patrick S.
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supporting information
p. 9499 - 9502
(2017/07/24)
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- C?H Cyanation of 6-Ring N-Containing Heteroaromatics
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Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C?H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.
- Elbert, Bryony L.,Farley, Alistair J. M.,Gorman, Timothy W.,Johnson, Tarn C.,Genicot, Christophe,Lallemand, Bénédicte,Pasau, Patrick,Flasz, Jakub,Castro, José L.,MacCoss, Malcolm,Paton, Robert S.,Schofield, Christopher J.,Smith, Martin D.,Willis, Michael C.,Dixon, Darren J.
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supporting information
p. 14733 - 14737
(2017/10/07)
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- COMPOUNDS USEFUL AS FAAH MODULATORS AND USES THEREOF
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Compounds are disclosed that have formula (I): where A, B, L1, X, W, Y, R1, R3, and nlare as defined herein. The compounds and pharmaceutical compositions thereof are useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, anxiety, depression, inflammation, cognitive disorders, weight and eating disorders, Parkinson's disease, Alzheimer's disease, spasticity, addiction, glaucoma, and others.
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Page/Page column 56-57
(2009/03/07)
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- PREPARATION OF PYRIDINE DERIVATIVES USING PYRIMIDINIUM DERIVATIVES AS INTERMEDIATES
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A method in which a pyridinium derivative of formula (I) such as 1,3-dimethyl-2,3-dihydro-2-oxopyrimidinium chloride is reacted with an acetyl compound of formula (II) such as 4-acetylpyridine, and then the reaction product is reacted with ammonia or an ammonium salt to form a pyridine derivative of formula (III):Also disclosed is a method for the preparation of the compound of formula (I) from reacting a compound of formula (IV) or (V) with a compound of formula (VI):Also disclosed are two additional alternative methods for the preparation of compounds of formula (I) and related compounds. The substituents are defined in the claims.
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Page/Page column 23
(2008/06/13)
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- Preparation of cyanopyridines by direct cyanation
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After pretreatment with nitric acid and trifluoroacetic anhydride, aqueous potassium cyanide converted pyridines 1a-1 into their corresponding 2-cyano derivatives 4a-1 in an average yield of 52%. Georg Thieme Verlag Stuttgart.
- Katritzky, Alan R.,Scriven, Eric F. V.,Majumder, Suman,Tu, Hongbin,Vakulenko, Anatoliy V.,Akhmedov, Novruz G.,Murugan, Ramiah
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p. 993 - 997
(2007/10/03)
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- A stereoselective process for the preparation of novel phosphonoalkylphosphinates
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We have devised both a contiguous and a stepwise strategy for the synthesis of the pyridylaminomethane-based class of phosphonoalkylphosphinates (PAPs) that form via the intermediacy of the phosphonoethoxyaminomethane XIa. The PAPs result from condensation of picolines and phosphonoacetals in high chemoselective yield. Following reduction of aminopyridine IIIb, the unprecedented Pt(0)-catalyzed epimerization of the chelated amidine [(hydroxy)methylphosphinyl]-[(3-methyl-2-piperidinyl-idene)amino]methylphosphonic acid (IIIa) yielded a single racemic pair of PAPs (IIIc). The epimerization was found to occur more slowly than amidine formation itself.
- Ebetino, Frank H.,Berk, Jeffrey D.
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p. 135 - 142
(2007/10/03)
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- Cobalt(I)-Catalyzed Cocyclotrimerization of Acetylene with 2,6-Dicyanopyridines
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A procedure of general application to the synthesis of alkyl-substituted 2-cyano-6-(2-pyridyl)pyridines from alkylpyridines is outlined.
- Chelucci, Giorgio,Cabras, M. Antonietta,Saba, A.
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p. 1289 - 1292
(2007/10/02)
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- Antipruritic composition
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An antipruritic composition for an oral medicine, injection, and external medicine, comprising an effective amount of a chelated zinc (e.g., zinc picolinate) as an antipruritic agent.
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- An Improved Synthesis of Homoproline and Derivatives
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An improved, general synthesis of substituted homoprolines has been developed by using readily available substituted pyridines (1).A key step in this synthetic procedure involves the known conversion of pyridine-N-oxides to 2-cyanopyridines (3) in nearly quantitative yields.The resulting nitriles are hydrolyzed to the corresponding pyridine-2-carboxylic acids (4).Subsequent reduction of the aromatic ring with PtO2/H2 gives the homoprolines (5) in good yields as racemic cis isomers.This procedure also can be utilized for the preparation of 5,6-benzohomoprolines fromthe appropriate quinoline precursors.The N-tert-butyloxycarbonyl (Boc) derivatives of these amino acids (useful intermediates for peptide synthesis) were also prepared in good yields.
- Shuman, Robert T.,Ornstein, Paul L.,Paschal, Jonathan W.,Gesellchen, Paul D.
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p. 738 - 741
(2007/10/02)
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- Site-Selectivity in the Cyanation of 3-Substituted Pyridine 1-Oxides with Trimethylsilanecarbonitrile
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The cyanation of 3-halo-, 3-methoxy-, and 3-dimethylaminopyridine 1-oxide with trimethylsilanecarbonitrile gave predominantly the corresponding 3-substituted 2-pyridinecarbonitriles.The deoxygenation of nitropyridine 1-oxides to nitropyridines with the same reagent is also described.Keywords - site-selective reaction; trimethylsilanecarbonitrile; pyridine 1-oxide; 2-pyridine-carbonitrile; nitropyridine 1-oxide; deoxygenation; aromatic amine N-oxide; cyanation
- Sakamoto, Takao,Kaneda, Soh-ichi,Nishimura, Sumiko,Yamanaka, Hiroshi
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p. 565 - 571
(2007/10/02)
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- Preparation of some Thiopyranopyridine Derivatives
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In the first systematic study of thiopyranopyridines in which the sulphur atom is separated from the pyridine ring by one carbon atom, the four isomeric enol esters, ethyl 5-hydroxy-8H-thiopyranopyridine-6-carboxylate (4b), ethyl 8-hydroxy-5H-thiopyranopyridine-7-carboxylate (5b), and ethyl 4-hydroxy-1H-thiopyrano- and pyridine-3-carboxylate (6b) and (7b), have been synthesised.Improved methods for the preparation of their pyridine precursors are described.With phenylhydrazine, the enol esters (4b) - (7b) give condensed pyrazole derivatives (15) - (18), which have dipolar structures; with hot mineral acid they undergo decarboxylative hydrolysis, to give the corresponding oxothiopyranopyridines (4a) - (7a).
- Clarke, Kenneth,Goulding, John,Scrowston, Richard M.
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p. 1501 - 1505
(2007/10/02)
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- 1-ACYLOXYPYRIDINIUM ION: THE REACTIVE INTERMEDIATE IN A MODIFIED REISSERT-HENZE REACTION
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Cyanation of 3-X-1-dimethylaminocarbonyloxypyridinium ions with trimethylsilanecarbonitrile or cyanide ion gives 3-methyl-2-pyridinecarbonitrile (ca.90percent) contaminated with 5-methyl-2-pyridinecarbonitrile (ca.10percent) when X = -CH3, and approximately equal amounts of the 3- and 5-X derivatives when X = -COOCH3.These product mixtures are identical to those obtained with the corresponding pyridine 1-oxides and dimethylcarbamoyl chloride in a modified Reissert-Henze reaction.
- Fife, Wilmer K.,Boyer, Brett D.
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p. 1121 - 1124
(2007/10/02)
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- Compounds with Bridgehead Nitrogen
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The position of conformational equilibra in 1,5-,1,6- and 1,8-dimethylperhydro-oxazolopyridines were determined by 1H NMR spectroscopy.The cis-(H-5,H-8a)-1,5-dimethylperhydro-oxazolopyridines adopted the trans fused conformation, as did the two isomers of cis-(H-1,H-8a)-1,6-dimethyl-perhydro-oxazolopyridine.In contrast, r-1,t-6,t-8a-1,6-dimethyl-perhydro-oxazolopyridine preferred the cis-fused conformation.Three of the 1,8-dimehylperhdro-oxazolopyridines adopted the trans-fused conformations (with distortion of the system in the case of the r-1,c-8,c-8a derivative) and the r-1,c-8,c-8a-1,8-dimethyl derivative adopted the cis-fused conformation.
- Crabb, Trevor A.,Heywood, Geoffrey C.
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p. 242 - 248
(2007/10/02)
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