1131-68-6

Usage

Uses

Used in Pharmaceutical Industry:
Quinoline-2-carbaldehyde oxime is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in Dye Industry:
quinoline-2-carbaldehyde oxime is used as a precursor in the synthesis of dyes, playing a crucial role in the production of colorants for various applications.
Used in Coordination Chemistry:
Quinoline-2-carbaldehyde oxime is used as a ligand for coordination compounds, enabling the formation of metal complexes with specific properties and applications.
Used in Antimicrobial Applications:
Due to its antimicrobial properties, quinoline-2-carbaldehyde oxime is used as an antimicrobial agent, helping to combat infections caused by various microorganisms.
Used in Anticancer Applications:
Quinoline-2-carbaldehyde oxime is used as an anticancer agent, potentially contributing to the development of new treatments for cancer by targeting and inhibiting the growth of cancer cells.
Used in Metal Complexation and Catalysis:
Leveraging its chelating properties, quinoline-2-carbaldehyde oxime is used in metal complexation and catalysis reactions, facilitating the development of new catalysts and chemical processes.

InChI:InChI=1/C10H8N2O/c13-11-7-9-6-5-8-3-1-2-4-10(8)12-9/h1-7,12H/b9-7+

Upstream product

• 5470-96-2 quinoline 2-carbaldehyde 
• 91-63-4 2-methylquinoline 
• 540-80-7 tert.-butylnitrite 

Downstream Products

• 5760-20-3 2-aminomethylquinoline 
• 1436-43-7 quinoline-2-carbonitrile 

Relevant academic research and scientific papers

From cyclopentadiene to isoxazoline-carbocyclic nucleosides; Synthesis of highly active inhibitors of influenza a virus H1N1

The synthesis of isoxazolino-carbocyclic nornucleosides incorporating a quinoline moiety was tuned through nitrosocarbonyl intermediate chemistry, and a range of adenine analogues were attained through the linear construction of purine heterocyclic rings. The synthesis hinges on exo-selective 1,3-dipolar cycloaddition of quinolinenitrile oxide to the 2,3-oxazanorborn-5-enes and simple elaboration of the cycloadducts. The nucleoside derivatives were initially tested for their inhibitory activity against a variety of viruses, including HBV, PTV and Flu A virus H1N1. High antiviral activities were found for compounds 22aA and 22bA in the case of Flu A H1N1. The synthesis of nornucleosides incorporating a quinoline moiety was tuned through the application of nitrosocarbonyl group chemistry. The synthesis hinges on exo-selective 1,3-dipolar cycloaddition of quinolinenitrile oxide to 2,3-oxazanorborn-5-enes and elaboration of the cycloadducts. The nucleosides were tested as inhibitors of a variety of viruses and some were found highly active against Flu A H1N1. Copyright

Structure, Spectroscopy, and Electrochemistry of Manganese(I) and Rhenium(I) Quinoline Oximes

Reactions of α- and β-diimine quinoline aldoximes with Mn(I) and Re(I) tricarbonyl halides afford quinoline oxime complexes. Both Mn(I) and Re(I) complexes experience severe geometric strain due to ligand steric interactions: 6-membered metallocycles exhibit more pronounced distortions than 5-membered ones, consistent with density functional theory structural analyses. Such distortions likely also affect reactivity patterns, as evidenced by Re(I)-induced deoximation of a quinoline variant containing a CF3-ketoxime.

The mechanism of the (bispidine)copper(ii)-catalyzed aziridination of styrene: A combined experimental and theoretical study

Experimental and DFT-based computational results on the aziridination mechanism and the catalytic activity of (bispidine)copper(I) and -copper(II) complexes are reported and discussed (bispidine = tetra- or pentadentate 3,7-diazabicyclo[3.1.1]-nonane derivative with two or three aromatic N donors in addition to the two tertiary amines). There is a correlation between the redox potential of the copper(II/I) couple and the activity of the catalyst. The most active catalyst studied, which has the most positive redox potential among all (bispidine)-copper(II) complexes, performs 180 turnovers in 30 min. A detailed hybrid density functional theory (DFT) study provides insight into the structure, spin state, and stability of reactive intermediates and transition states, the oxidation state of the copper center, and the denticity of the nitrene source. Among the possible pathways for the formation of the aziridine product, the stepwise formation of the two N-C bonds is shown to be preferred, which also follows from experimental results. Although the triplet state of the catalytically active copper nitrene is lowest in energy, the two possible spin states of the radical intermediate are practically degenerate, and there is a spin crossover at this stage because the triplet energy barrier to the singlet product is exceedingly high.

Conversion of 2-(aminomethyl) substituted pyridine and quinoline to their dicarbonyldiimides using copper(II) acetate

In air, hydrated ethanolic (95%) solution of 2-(aminomethyl) substituted pyridine and quinoline, on stirring with half equivalent of Cu(OAc)2·H2O, respectively afforded [Cu(bpca)(OAc)(H2O)]·H2O (1) and [Cu(bqca)(OAc)(H2O)] (2) {bpca = bis(2-pyridylcarbonyl)diimide ion and bqca = bis(2-quinolylcarbonyl)diimide ion} in good yields. These reactions involve oxidation of the methylene group and formation of the bond between nitrogen and carbon in N-C({double bond, long}O) through coupling. The complex [Cu(pqca)(OAc)(H2O)]3[Cu2(OAc)4(EtOH)2]1.5 (3) {pqca = (2-pyridylcarbonyl)(2-quinolylcarbonyl)diimide ion} was synthesized by stirring an ethanolic solution of the Schiff base [(2-pyridyl)-N-((2-quinolyl)methylene)methanamine] (L1) and with one equivalent of Cu(OAc)2·H2O. A plausible mechanism for the conversion has been proposed. The free ligands were isolated as crystalline solids from compounds 1-3, by extrusion of Cu2+ ion using EDTA2-. The molecular structures of 1-3 and bqcaH were established by X-ray crystallography and compounds having quinolyl group have π-stacking interactions.

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

Synthesis and antiproliferative properties of isoxazole analogs containing dibenzosuberane moiety

A series of twelve novel isoxazole analogs containing dibenzosuberane moiety were synthesized using convergent synthesis approach. Newly synthesized compounds were well characterized by mass spectroscopy, IR and NMR spectroscopy. All the compounds were screened for their antiproliferative property against HepG2 and HeLa cell lines. Among them, compounds 7a, 7b, 7c, 7g and 7h were found active against both HepG2 and HeLa cell lines. Graphical Abstract: Twelve analogs of isoxazole containing dibenzosuberane moiety (7a-l) were synthesized, characterized and evaluated for their antiproliferative activity. [Figure not available: see fulltext.]

Copper(ii)-promoted direct conversion of methylarenes into aromatic oximes

A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.

Copper(II)-promoted direct conversion of methylarenes into aromatic oximes

A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.

Effective conversion of heteroaromatic ketones into primary amines via hydrogenation of intermediate ketoximes

A process to access heteroaromatic primary amines from the corresponding heteroaromatic ketones has been developed. A broad range of previously reported methods to convert ketones to primary amines was examined on heterocyclic ketones without success, including Leuckart-Wallach conditions, borane reductions, and transition-metal-catalyzed hydrogenations. Unique among the catalysts examined, Raney cobalt produced the desired primary heterocyclic amine. Raney cobalt hydrogenation of structurally varied heterocyclic ketoximes was demonstrated to form primary amines in good selectivity under mild conditions, and the products are easily isolated in high yield. Additionally, this is the first report of a systematic evaluation of the capabilities of Raney cobalt as an oxime hydrogenation catalyst.

Bronsted acid catalyzed benzylic C-H bond functionalization of azaarenes: Nucleophilic addition to nitroso compounds

A practical Bronsted acid promoted benzylic C-H functionalization of 2-alkylazaarenes and nucleophilic addition to nitroso compounds was developed under mild conditions. Switched by Bronsted acids, this method can afford azaarene-2-aldimines, azaarene-2-carbaldehyde, or azaarene-2-oximes selectively. No metal, base, oxidant, or other additives were required.