14906-37-7

Usage

Uses

Used in Chemical Synthesis:
Ethyl isonicotinate N-oxide is used as a chemical intermediate for the preparation of different chemical products. Its role in synthesis is crucial for the production of a variety of compounds, contributing to the chemical industry's diverse applications.
Due to the limited information available on Ethyl isonicotinate N-oxide, it is essential to handle Ethyl isonicotinate N-oxide with caution until more data on its safety, toxicity, and environmental impact is obtained. This ensures responsible and safe usage in chemical processes.

InChI:InChI=1/C8H9NO3/c1-2-12-8(10)7-3-5-9(11)6-4-7/h3-6H,2H2,1H3

Upstream product

• 1570-45-2 isonicotinic acid ethylester 
• 55-22-1 pyridine-4-carboxylic acid 

Downstream Products

• 6313-54-8 2-chloroisonicotinic acid, 
• 38557-82-3 4-pyridine carboxamide 1-oxide 
• 6975-73-1 1-oxide pyridine-4-carbohydrazide 
• 58481-14-4 2-cyano-isonicotinic acid ethyl ester 
• 78815-66-4 5-benzoyl-4-ethoxycarbonyl-2-(3-methoxyphenyl)pyridine 
• 1570-45-2 isonicotinic acid ethylester 
• 102078-89-7 4-ethoxycarbonyl-2,6-diphenylpyridine 
• 13602-12-5 Isonicotinic acid N-oxide 
• 1582284-16-9 ethyl 2-(4-phenyl-1H-1,2,3-triazol-1-yl)isonicotinate 
• 1286763-45-8 4-ethoxycarbonyl-2-(2-phenylquinolin-4-yl)pyridine N-oxide 
• 148332-31-4 4’-ethoxycarbonyl-2,2’:6’,2’’-terpyridine 
• 54453-93-9 ethyl 2-chloroisonicotinate 
• 100868-12-0 1-oxy-isonicotinic acid vanillylidenehydrazide 

Relevant academic research and scientific papers

4-Pyridyl carbonyl and related compounds as thrips lures: Effectiveness for onion thrips and New Zealand flower thrips in field experiments

On the basis of structural and/or aroma analogies to known thrips (Thysanoptera: Thripidae) lures, 35 compounds (18 pyridine derivatives, 13 benzene derivatives, and 4 other compounds), consisting of both synthetic and naturally occurring compounds, were screened for their ability to bring about increased thrips capture in field experiments using water traps in Canterbury, New Zealand. Most of the thrips caught were New Zealand flower thrips (NZFT) (Thrips obscuratus) or onion thrips (OT) (Thrips tabaci). The greatest increase in capture for NZFT (158 times for ♀ cf. to water control) was for the known lure ethyl nicotinate, a 3-pyridyl ester. Ethyl isonicotinate, the 4-pyridyl regioisomer of ethyl nicotinate, not previously reported as a thrips lure, provided the greatest increases in capture for OT (31 times) of any of the compounds tested, significantly more than ethyl nicotinate. Other 4-pyridyl carbonyl compounds, including ethyl 4-pyridyl ketone, also increased OT capture significantly. The natural floral compound cis-jasmone, which increased trap capture of NZFT (♀ 42 times, ♂ 25 times) but not OT, is reported as a thrips lure for the first time.

Evolutionary Design of Low Molecular Weight Organic Anolyte Materials for Applications in Nonaqueous Redox Flow Batteries

The integration of renewable energy sources into the electric grid requires low-cost energy storage systems that mediate the variable and intermittent flux of energy associated with most renewables. Nonaqueous redox-flow batteries have emerged as a promising technology for grid-scale energy storage applications. Because the cost of the system scales with mass, the electroactive materials must have a low equivalent weight (ideally 150 g/(mol·e-) or less), and must function with low molecular weight supporting electrolytes such as LiBF4. However, soluble anolyte materials that undergo reversible redox processes in the presence of Li-ion supports are rare. We report the evolutionary design of a series of pyridine-based anolyte materials that exhibit up to two reversible redox couples at low potentials in the presence of Li-ion supporting electrolytes. A combination of cyclic voltammetry of anolyte candidates and independent synthesis of their corresponding charged-states was performed to rapidly screen for the most promising candidates. Results of this workflow provided evidence for possible decomposition pathways of first-generation materials and guided synthetic modifications to improve the stability of anolyte materials under the targeted conditions. This iterative process led to the identification of a promising anolyte material, N-methyl 4-acetylpyridinium tetrafluoroborate. This compound is soluble in nonaqueous solvents, is prepared in a single synthetic step, has a low equivalent weight of 111 g/(mol·e-), and undergoes two reversible 1e- reductions in the presence of LiBF4 to form reduced products that are stable over days in solution.

Fluorovinylsulfones and -Sulfonates as Potent Covalent Reversible Inhibitors of the Trypanosomal Cysteine Protease Rhodesain: Structure-Activity Relationship, Inhibition Mechanism, Metabolism, and in Vivo Studies

Rhodesain is a major cysteine protease of Trypanosoma brucei rhodesiense, a pathogen causing Human African Trypanosomiasis, and a validated drug target. Recently, we reported the development of α-halovinylsulfones as a new class of covalent reversible cysteine protease inhibitors. Here, α-fluorovinylsulfones/-sulfonates were optimized for rhodesain based on molecular modeling approaches. 2d, the most potent and selective inhibitor in the series, shows a single-digit nanomolar affinity and high selectivity toward mammalian cathepsins B and L. Enzymatic dilution assays and MS experiments indicate that 2d is a slow-tight binder (Ki = 3 nM). Furthermore, the nonfluorinated 2d-(H) shows favorable metabolism and biodistribution by accumulation in mice brain tissue after intraperitoneal and oral administration. The highest antitrypanosomal activity was observed for inhibitors with an N-terminal 2,3-dihydrobenzo[b][1,4]dioxine group and a 4-Me-Phe residue in P2 (2e/4e) with nanomolar EC50 values (0.14/0.80 μM). The different mechanisms of reversible and irreversible inhibitors were explained using QM/MM calculations and MD simulations.

From Pyridine- N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy

The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operates at ambient temperature and tolerates sensitive functional groups, enabling the synthesis of otherwise challenging compounds.

Reaction of Pyridine-N-Oxides with Tertiary sp2-N-Nucleophiles: An Efficient Synthesis of Precursors for N-(Pyrid-2-yl)-Substituted N-Heterocyclic Carbenes

N-(Pyrid-2-yl)-substituted azolium and pyridinium salts, precursors for hybrid NHC-containing ligands, were obtained with excellent regioselectivity, employing a deoxygenative CH-functionalization of pyridine-N-oxides with substituted imidazoles, thiazoles, and pyridine. Unlike the traditional SNAr-based methods, this approach provides high yields for substrates bearing substituents of different electronic nature. The utility of azolium and pyridinium salts thus prepared was also highlighted by the synthesis of pyridyl-substituted imidazolyl-2-thione, benzodiazepine as well as 2-aminopyridines.

Visible Light-Mediated Decarboxylative Alkylation of Pharmaceutically Relevant Heterocycles

A net redox-neutral method for the decarboxylative alkylation of heteroarenes using photoredox catalysis is reported. Additionally, this method features the use of simple, commercially available carboxylic acid derivatives as alkylating agents, enabling the facile alkylation of a variety of biologically relevant heterocyclic scaffolds under mild conditions.

Synthesis of unsymmetrically substituted bipyridines by palladium-catalyzed direct C-H arylation of pyridine N -oxides

Chemical equations presented. Substituted bipyridines were efficiently prepared by direct coupling between pyridine N-oxides and halopyridines using a palladium catalyst. Pyridine N-oxides with electron-withdrawing substitutents gave the best yields. This method allows the convenient preparation of 2,2′-, 2,3′-, and 2,4′-bipyridines which are useful as functionalized ligands for metal complexes or as building blocks for supramolecular architectures.

INSECT BEHAVIOUR MODIFYING COMPOUNDS

The invention provides methods for controlling thrips populations using thrips-repelling and/or thrips-attracting agents. The agents are derivatives of pyridine. The invention also provides methods of preventing or minimising damage to plants by use of the same.

FUROISOQUINOLINE DERIVATIVES, PROCESS FOR PRODUCING THE SAME AND USE THEREOF

A compound having a partial structure represented by Formula: or a salt thereof has an excellent phosphodiesterase (PDE) IV-inhibiting effect, and is useful as a prophylactic or therapeutic agent against inflammatory diseases, for example, bronchial asthma, chronic obstructive pulmonary disease (COPD), rheumatoid arthritis, autoimmune disease, diabetes and the like.

A practical, efficient, and rapid method for the oxidation of electron deficient pyridines using trifluoroacetic anhydride and hydrogen peroxide- urea complex

A general method for the oxidation of electron-poor pyridines to their N-oxides using UHP and TFAA in either CH2Cl2 or CH3CN was developed. The methodology proved to tolerate a number of functional groups and substitution