- A novel reagent combination for the oxidation of highly electron deficient pyridines to N-oxides: trifluoromethanesulfonic anhydride/sodium percarbonate
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A novel reagent combination, Tf2O/Na2CO3·1.5H2O2, has been developed for the oxidation of highly electron deficient pyridines to their corresponding N-oxides. The N-oxidation reaction, utilizing the in situ generated peracid, proceeds under mild conditions that allow for a number of functional groups and substitution patterns on the pyridine ring.
- Zhu, Xizhen,Kreutter, Kevin D.,Hu, Huaping,Player, Mark R.,Gaul, Micheal D.
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- INHIBITOR COMPOUNDS
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The disclosure relates to heterocyclic compounds and methods for their preparation. The disclosure provides compounds that may have beneficial therapeutic activity in the treatment of a disease or condition mediated by excessive or otherwise undesirable Des1 and/or fibrotic activity.
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Page/Page column 63; 75
(2021/01/29)
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- Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls
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2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.
- Dubovtsev, Alexey Yu.,Shcherbakov, Nikolay V.,Dar'in, Dmitry V.,Kukushkin, Vadim Yu.
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p. 745 - 757
(2020/02/04)
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- IMIDAZO[1,2-A]PYRIDINE DERIVATIVES AS HISTONE DEMETHYLASE INHIBITORS
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This disclosure relates, inter alia, to compounds that inhibit histone demethylase activity. In particular, the disclosure relates to compounds that inhibit histone lysine demethylase KDM5B, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions disclosed herein.
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Paragraph 0140
(2018/01/15)
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- Highly efficient and selective phosphorylation of amino acid derivatives and polyols catalysed by 2-aryl-4-(dimethylamino)pyridine-N-oxides-towards kinase-like reactivity
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The chemoselective phosphorylation of hydroxyl containing amino acid derivatives and polyols by phosphoryl chlorides catalyzed by 2-aryl-4-(dimethylamino)pyridine-N-oxides is described.
- Murray, James I.,Woscholski, Rudiger,Spivey, Alan C.
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supporting information
p. 13608 - 13611
(2015/01/09)
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- 4-Substituted 1-acyloxypyridine-2(1H)-thiones: Experimental and computational studies of the substituent effect on electronic absorption spectra
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(Chemical Equation Presented) A series of eight 4-substituted 1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thiones (1, X=H, OC7H 15, Me, CF3, SC3H7, CN, COOMe, and Cl) was prepared and characterized by UV-vis spectroscopy in MeCN and cyclohexane. The observed lowest energy transition, designated as πCS→ π*ring, exhibits a substantial substituent effect and λmax ranges from 333 (X=OC 7H15) to 415 nm (X=CN). Experimental λ max values for all esters except for 1b (X=OC7H 15) correlate with the σp - parameter (ρ = 0.41 ± 0.03, r2= 0.95). In contrast, the energy of the absorption band at about 295 nm, designated as πCS → π*CS, is practically substituent independent. Both absorption bands exhibit a modest negative solvatochromic effect. The experimental absorption energies correlate better with excitation energies calculated for N-acetyloxy analogues 2 with the ZINDO//DFT than with the TD-DFT//DFT method. Calculations for a series of 12 N-acetates 2 predict the most blueshifted π → π* transition for the alkoxy substituent and most red-shifted for the NO2 group relative to the parent 2a (X = H). 2009 American Chemical Society.
- Jankowiak, Aleksandra,Kaszynski, Piotr
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supporting information; experimental part
p. 7441 - 7448
(2010/01/16)
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- PYRIDINE DERIVATIVES AND THEIR USE AS MEDICAMENTS FOR TREATING DISEASES RELATED TO MCH RECEPTOR
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The present invention encompasses novel substituted pyridine compounds of Formula (I), which act as MCH receptor antagonists. These compositions and pharmaceutical compositions thereof are useful in the prophylaxis or treatment of improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure, obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia, myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit disorder, substance abuse disorders and dyskinesias including Parkinson's disease, epilepsy, and addiction.
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Page/Page column 82
(2010/10/20)
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- Fluorinated pyridine N-oxide thrombin modulators and process for N-oxidation of nitrogen containing heteroaryls
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The present invention describes compounds of Formula I or a pharmaceutically acceptable salt thereof, for the prophylaxis, or treatment of diseases and conditions related to thrombin activity in a mammal. The present invention also relates to a novel method of N-oxidation of nitrogen containing heteroaryls.
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Page/Page column 9
(2008/06/13)
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- THE REACTION OF 4-CHLOROPYRIDINE 1-OXIDES WITH ACTIVATED ACETYLENES. A CONVENIENT ONE-STEP SYNTHESIS OF FUROPYRIDINES
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The reaction of 4-chloro- and 4-pseudohalogeno-pyridine 1-oxides with activated acetylenes (phenylcyanoacetylene, methyl phenylpropiolate, phenylpropiolaldehyde, methyl propiolate, and ethynyl p-tolyl sulphone) gave good yields of substituted furopyridines 7.With 1-phenyl-2-methanesulphonylacetylene under mild conditions the initial -shift product 9 was isolated and converted to 7 with base.The structure of 7 was established unambiguously by using Eu(fod)3-induced NMR shifts.The mechanism of the reaction is discussed briefly and consecutive -shifts are proposed to account for the formation 7.
- Abramovitch, Rudolph A.,Deeb, Ali,Kishore, Dharma,Mpango, George B. W.,Shinkai, Ishiro
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p. 167 - 172
(2007/10/02)
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