14906-59-3

Usage

Chemical Properties

Pale-Green Solid

Uses

Different sources of media describe the Uses of 14906-59-3 differently. You can refer to the following data:
1. Anti-bacterial agent.
2. Anti-bacterial agent

InChI:InChI=1/C6H4N2O/c7-5-6-1-3-8(9)4-2-6/h1-4H

Upstream product

• 38557-82-3 4-pyridine carboxamide 1-oxide 
• 100-48-1 pyridine-4-carbonitrile 
• 24145-27-5 (Z)-(1-oxidopyridin-1-ium-4-yl)-4-carbaldoxime 
• 24145-29-7 (E)-4-pyridinecarbaldehyde 1-oxide oxime 
• 151-50-8 potassium cyanide 

Downstream Products

• 29181-50-8 2,4-Dicyanopyridine 
• 63919-16-4 Thioisonicotinamid-1-oxid 
• 100-48-1 pyridine-4-carbonitrile 
• 94805-51-3 2-hydroxyisonicotinonitrile 
• 124300-46-5 2-(phenylethynyl)isonicotinonitrile 
• 1453-82-3 isonicotinamide 
• 33252-30-1 2-chloro-4-pyridinenitrile 
• 570396-89-3 3-naphthalen-1-yl-isonicotinonitrile 
• 570396-90-6 1-benzyl-5-(1-naphthyl)-1,2,3,6-tetrahydropyridine-4-carbonitrile 
• 570396-93-9 1-{[(4-cyanobenzyl)amino]acetyl}-5-(1-naphthyl)-1,2,3,6-tetrahydropyridine-4-carbonitrile 
• 570396-96-2 1-[(R)-2-Amino-3-(4-cyano-phenyl)-propionyl]-5-naphthalen-1-yl-1,2,3,6-tetrahydro-pyridine-4-carbonitrile 

Relevant academic research and scientific papers

Visible-Light-Mediated C-H Alkylation of Pyridine Derivatives

We report herein a visible-light-mediated C-H alkylation of pyridine derivatives that proceeds by simple combination of a large variety of N-alkoxypyridinium ions with alkanes in the presence of 2 mol % of fac-Ir(ppy)3 under blue illumination. The mild reaction conditions together with the high group functional tolerance make of this process a useful synthetic platform for the construction of structurally strained heterocycles. Detailed mechanistic investigations, including density functional theory calculations and quantum yield measurement, allowed us to understand factors controlling the reactivity and the selectivity of the reaction.

A Biocatalytic Synthesis of Heteroaromatic N-Oxides by Whole Cells of Escherichia coli Expressing the Multicomponent, Soluble Di-Iron Monooxygenase (SDIMO) PmlABCDEF

Aromatic N-oxides (ArN?OX) are desirable biologically active compounds with a potential for application in pharmacy and agriculture industries. As biocatalysis is making a great impact in organic synthesis, there is still a lack of efficient and convenient enzyme-based techniques for the production of aromatic N-oxides. In this study, a recombinant soluble di-iron monooxygenase (SDIMO) PmlABCDEF overexpressed in Escherichia coli was showed to produce various aromatic N-oxides. Out of 98 tested N-heterocycles, seventy were converted to the corresponding N-oxides without any side oxidation products. This whole-cell biocatalyst showed a high activity towards pyridines, pyrazines, and pyrimidines. It was also capable of oxidizing bulky N-heterocycles with two or even three aromatic rings. Being entirely biocatalytic, our approach provides an environmentally friendly and mild method for the production of aromatic N-oxides avoiding the use of strong oxidants, organometallic catalysts, undesirable solvents, or other environment unfriendly reagents. (Figure presented.).

Electrochemical Deoxygenation of N-Heteroaromatic N -Oxides

An electrochemical method for the deoxygenation of N-heteroaromatic N -oxide to give the corresponding N-heteroaromatics has been developed. Several classes of N-heterocycles such as pyridine, quinoline, isoquinoline, and phenanthridine are tolerated. The electrochemical reactions proceed efficiently in aqueous solution without the need for transition-metal catalysts and waste-generating reducing reagents.

Synthesis method of topiroxostat

The invention belongs to the field of medicine and chemical industry and discloses a synthesis method of topiroxostat. The method comprises that 4-cyanopyridine as a starting raw material is oxidized by hydrogen peroxide to form an intermediate 1, the intermediate 1, sodium methoxide and ammonium chloride undergo a reaction to produce an intermediate 2, the intermediate 2 and 4-cyanopyridine undergo an annulation reaction under action of cuprous bromide and sodium carbonate to produce an intermediate 3, and the intermediate 3 and trimethylsilyl cyanide undergo a cyanation reaction to produce topiroxostat. The method utilizes low-price 4-cyanopyridine as a starting raw material, and in the first reaction step, methanol is used as a solvent and 4-cyanopyridine nitrogen oxide as the intermediate 1 is prepared. The method has a high yield and produces a high-purity product. The whole route is easy to operate and is conducive to industrial mass production.

Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C-H functionalization of pyridine: N -oxides

A novel solvent- and halide-free atom-economical synthesis of practically useful pyridine-2-yl substituted ureas utilizes easily accessible or commercially available pyridine N-oxides (PyO) and dialkylcyanamides. The observed C-H functionalization of PyO is suitable for the good-to-high yielding synthesis of a wide range of pyridine-2-yl substituted ureas featuring electron donating and electron withdrawing, sensitive, or even fugitive functional groups at any position of the pyridine ring (63-92%; 19 examples). In the cases of 3-substituted PyO, the C-H functionalization occurs regioselectively providing a route for facile generation of ureas bearing a 5-substituted pyridine-2-yl moiety.

Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines

Herein, we report a simple and metal-free method for the synthesis of N-azine sulfoximines by the nucleophilic substitution of azine N-oxides with NH-sulfoximines. The present method works at room temperature with wide functional group compatibility and gives several unprecedented N-azine sulfoximines. The reaction conditions were also found suitable with enantiopure substrates and furnished products without any racemization. It also finds an application in the sulfoximination of azine-based functional molecules such as 2,2′-bipyridine, 1,10-phenanthroline, and quinine.

Insights into the mechanistic and synthetic aspects of the Mo/P-catalyzed oxidation of N-heterocycles

A Mo/P catalytic system for an efficient gram-scale oxidation of a variety of nitrogen heterocycles to N-oxides with hydrogen peroxide as terminal oxidant has been investigated. Combined spectroscopic and crystallographic studies point to the tetranuclear Mo4P peroxo complex as one of the active catalytic species present in the solution. Based on this finding an optimized catalytic system has been developed. The utility and chemoselectivity of the catalytic system has been demonstrated by the synthesis of over 20 heterocyclic N-oxides.

PROCESS FOR MAKING AND USING HOF.RCN

The invention relates to a process for making HOF.RCN and using it to oxidise organic substrates in a quick and safe way. The process comprises passing diluted fluorine through a conduit and RCN in water through another conduit into a microreactor to form HOF.RCN and reacting this with an organic substrates.

Oxidation of organic compounds by sulfonated porous carbon and hydrogen peroxide

The oxidation of organic compounds by sulfonated porous carbon and H 2O2 was studied at room temperature. Alkyl and aryl sulfides were oxidized to the corresponding sulfoxides or sulfones in excellent yields. Secondary alcohols were also converted to the corresponding esters/lactones and aldehydes to methyl esters in good yields. Moreover, aliphatic tertiary amines and substituted pyridines were oxidized to N-oxides.

Synthesis and structure-activity relationship of Huprine derivatives as human acetylcholinesterase inhibitors

New series of Huprine (12-amino-6,7,10,11-tetrahydro-7,11-methanocycloocta[b]quinolines) derivatives have been synthesized and their inhibiting activities toward recombinant human acetylcholinesterase (rh-AChE) are reported. We have synthesized two series of Huprine analogues; in the first one, the benzene ring of the quinoline moiety has been replaced by different heterocycles or electron-withdrawing or electron-donating substituted phenyl group. The second one has been designed in order to evaluate the influence of modification at position 12 where different short linkers have been introduced on the Huprine X, Y skeletons. All these molecules have been prepared from ethyl- or methyl-bicyclo[3.3.1]non-6-en-3-one via Friedlaender reaction involving selected o-aminocyano aromatic compounds. The synthesis of two heterodimers based on these Huprines has been also reported. Activities from moderate to same range than the most active Huprines X and Y taken as references have been obtained, the most potent analogue being about three times less active than parent Huprines X and Y. Topologic data have been inferred from molecular dockings and variations of activity between the different linkers suggest future structural modifications for activity improvement.