89060-22-0

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxy-quinoline-2-carbaldehyde is used as a building block for the synthesis of various biologically active molecules. It plays a crucial role in the development of antimalarial and antibacterial agents due to its unique chemical structure that allows for the creation of a wide range of therapeutic compounds.

InChI:InChI=1/C11H9NO2/c1-14-9-2-3-11-10(6-9)8(7-13)4-5-12-11/h2-7H,1H3

Upstream product

• 1078-28-0 6-methoxyquinaldine 
• 201230-82-2 carbon monoxide 
• 476161-59-8 2--bromo--6--methoxyquinoline 
• 613-21-8 6-hydroxyquinaldine 
• 123-30-8 4-amino-phenol 
• 104-94-9 4-methoxy-aniline 
• 67-56-1 methanol 
• 5263-87-6 6-methoxy quinoline 
• 856095-00-6 4-bromo-6-methoxy-2-methylquinoline 
• 15644-90-3 6-methoxy-2-methylquinolin-4-ol 

Downstream Products

• 75433-99-7 6-Methoxy-quinoline-2-carboxylic acid 
• 1426679-11-9 7'-chloro-2-tosyl-1,2,3,3',4',9-hexahydro-1'H-spiro[pyrido[3,4-b]indole-4,2'-quinoline] 
• 1426678-86-5 N-((1H-indol-2-yl)methyl)-N-((7-chloroquinolin-2-yl)methyl)-4-methylbenzenesulfonamide 
• 21535-78-4 3-benzyl-8-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline 
• 1044900-36-8 N-({(4aS,R)-3-[(4'-chloro-[1,1'-biphenyl]-2-yl)methyl]-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinolin-8-yl}carbonyl)-4-({(1R)-3-(dimethylamino)-1-[(phenyl-sulphanyl)methyl]propyl}amino)-3-nitrobenzenesulphonamide 
• 1053265-04-5 (4aS,R)-3-[(4'-chloro-[1,1'-biphenyl]-2-yl)methyl]-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylic acid hydrochloride 
• 1053265-03-4 methyl (4aS,R)-3-[(4'-chloro-[1,1'-biphenyl]-2-yl)methyl]-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate 
• 1053265-01-2 methyl (4aS,R)-3-benzyl-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]-quinoline-8-carboxylate 
• 1053266-42-4 Methyl 3-(2-phenoxybenzyl)-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate 
• 1053265-27-2 (4aS)-8-methoxy-3-[(2S)-2-methoxy-2-phenylethanoyl]-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline 

Relevant academic research and scientific papers

Iodine-catalyzed oxidative annulation: Facile synthesis of pyrazolooxepinopyrazolones: Via methyl azaarene sp3C-H functionalization

An iodine-catalyzed methyl azaarene sp3 C-H functionalization has been developed for the synthesis of a seven-membered O-heterocyclic architecture containing three different heterocyclic aromatic hydrocarbons. This method can be applied to a wide range of substituted methyl azaarenes and diverse 2,4-dihydro-3H-pyrazol-3-ones, and brings about the efficient preparation of 2,9-dihydrooxepino[2,3-c:6,5-c′]dipyrazol-3(7H)-ones in high yields with the merits of low catalyst loading, good functional group tolerance and metal-free conditions.

Methanol as a formylating agent in nitrogen heterocycles

A radical mediated C-H direct formylation of N-heteroarenes with methanol is reported. The reaction features a novel iron-catalyzed Minisci oxidative coupling process using commercially available methanol as a formylating reagent. It effectively solved the long-standing problems associated with using methanol as a formylating reagent in these types of reactions. Compared to the traditional Minisci C-H formylation methods, this protocol is highly atom-economical, simple to operate, and environmentally friendly and shows good functional group tolerance. This Minisci formylation strategy is a straightforward approach for the late-stage functionalization of N-heteroarenes. This journal is

Novel quinoline-based fluorescent bioimaging probe, KSNP117, for sentinel lymph node mapping

Fluorescent imaging agents with biocompatibility and high sensitivity are urgently required for the accurate detection of sentinel lymph nodes (SLNs). Herein, we report the design of a novel quinoline-based fluorescent probe, designated KSNP117, which can be applied as a biomedical imaging agent in the sensitive and quantitative detection of SLNs. KSNP117 exerted no adverse effects on the proliferation of ovary and immune cells and also showed excellent serum stability with photo-brightening effects.In vivofluorescent imaging revealed the accumulation of KSNP117 in the SLNs of nude mice within 10 min post injection, withoutin vivotoxicity, which was consistent with the findings ofex vivoimaging. These results support the potential of KSNP117 as a promising lymphatic tracer for biomedical imaging applications.

NOVEL COMPOUNDS USEFUL AS NEAR-INFRARED FLUORESCENT PROBES SELECTIVELY BINDING TO TAU AGGREGATES AND METHOD OF PREPARING THE SAME

Disclosed are a compound with near-infrared fluorescence that selectively binds to tau aggregates, a method for preparing the same, a tau-targeting near-infrared fluorescent probe including the compound, a composition for detecting a tau fiber protein containing the near-infrared fluorescent probe as an active ingredient, and the use of the composition for the diagnosis of tauopathy. In particular, the compound does not bind to an amyloid beta protein and has high selectivity to a tau aggregate, specifically reported as an etiology of the initial state of tauopathy, thus being useful as a near-infrared fluorescent detector for detecting a tau fiber protein for early diagnosis of a tauopathy including Alzheimer's disease.

Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls

An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.

Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.

Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.

A water soluble ratiometric fluorescent probe for targeting SO2in mitochondria based on conjugated biquinolines

Despite the unprecedented development of SO2 fluorescent probes in the past five years, the water-solubility of these probes is still an important factor related to their practical application. In previous work, we have studied SO2 detection by coupling quinoline and coumarin. Although the water solubility of the probe was improved, SO2 detection in a 100% aqueous medium was not fully achieved. Therefore, based on the previous system, we conjugated two quinolines to realize a 100% water-soluble sulfur dioxide fluorescent probe. The Probe showed a large Stokes shift (170 nm). Besides, the Probe could respond to SO2 within 1.5 min with high selectivity and sensitivity (LOD = 0.29 μM). In addition, fluorescence co-localization studies suggested that the Probe could be used for monitoring SO2 in the mitochondria of HeLa cells and living mice. It is believed that such an excellent probe will have a wide application prospect in the future. This journal is

Metal- and radical-free aerobic oxidation of heteroaromatic methanes: An efficient synthesis of heteroaromatic aldehydes

A metal-free and radical-free synthesis of heteroaromatic aldehydes was developed through aerobic oxidation of methyl groups in an I2/DMSO/O2 catalytic system. Under the reaction conditions, various functional groups such as methoxy, aldehyde, ester, nitro, amide, and halo (F, Cl, Br) groups were well tolerated. The bioactive compounds like chlorchinaldin derivative and papaverine were also oxidized to the corresponding aldehydes and ketones. This reaction provided an efficient method for preparing the valuable heteroaromatic aldehydes.

Consecutive Intermolecular Reductive Amination/Asymmetric Hydrogenation: Facile Access to Sterically Tunable Chiral Vicinal Diamines and N-Heterocyclic Carbenes

A highly enantioselective iridium- or ruthenium-catalyzed intermolecular reductive amination/asymmetric hydrogenation relay with 2-quinoline aldehydes and aromatic amines has been developed. A broad range of sterically tunable chiral N,N′-diaryl vicinal diamines were obtained in high yields (up to 95 %) with excellent enantioselectivity (up to >99 % ee). The resulting chiral diamines could be readily transformed into sterically hindered chiral N-heterocyclic carbene (NHC) precursors, which are otherwise difficult to access. The usefulness of this synthetic approach was further demonstrated by the successful application of one of the chiral vicinal diamines and chiral NHC ligands in a transition-metal-catalyzed asymmetric Suzuki–Miyaura cross-coupling reaction and asymmetric ring-opening cross-metathesis, respectively.