22615-00-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromoquinoline-1-oxide is used as a synthetic intermediate for the production of various pharmaceuticals, contributing to the development of new drugs and improving existing ones.
Used in Agrochemical Industry:
3-Bromoquinoline-1-oxide is used as a synthetic intermediate in the production of agrochemicals, aiding in the creation of effective pesticides and other agricultural chemicals.
Used in Organic Synthesis:
3-Bromoquinoline-1-oxide is used as a reagent in organic synthesis, facilitating the creation of new chemical compounds and enhancing the synthesis process.
Used in Medicinal Chemistry Research:
3-Bromoquinoline-1-oxide is used as a research compound in medicinal chemistry, exploring its potential anti-inflammatory, antibacterial, and anticancer properties for the development of novel therapeutic agents.

InChI:InChI=1/C9H6BrNO/c10-8-5-7-3-1-2-4-9(7)11(12)6-8/h1-6H

Upstream product

• 5332-24-1 3-bromoquinoline 
• 2508-86-3 4-aminoquinoline 1-oxide 
• 58550-94-0 3-bromo-1-oxy-quinolin-4-ylamine 

Downstream Products

• 939-16-2 3-Bromcarbostyril 
• 101870-60-4 3-bromo-2-chloro-quinoline 
• 3749-18-6 3-bromo-6-nitroquinoline-N-oxide 
• 101422-51-9 1-benzoyloxy-3-bromo-6-nitro-1H-quinolin-2-one 
• 59119-39-0 2-(3-morpholin-4-yl-quinolin-2-yl)-cyclohexanone 
• 52448-21-2 3-phenyl-3H-oxazolo[4,5-b]quinolin-2-one 
• 76278-28-9 4-(3-Bromo-quinolin-2-yl)-2-phenyl-4H-oxazol-5-one 
• 83492-23-3 5-(3-Bromo-quinolin-2-yl)-2-phenyl-thiazol-4-one 
• 74421-87-7 3-(phenylcyanomethyl)-quinoline 1-oxide 
• 83819-56-1 4-(3-bromo-2-quinolyl)dimedone 
• 83819-55-0 3-acetoxy-2-(3-bromo-2-quinolyl)-5,5-dimethyl-2-cyclohexanone 
• 81327-24-4 2-(3-Bromo-1-oxy-quinolin-2-yl)-1-phenyl-ethanone 
• 939-16-2 3-bromoquinolin-2-one 
• 137470-12-3 N-(3-bromo-2-quinolyl)-3-bromo-2-quinolinone 

Relevant academic research and scientific papers

A concise synthesis of a novel antiangiogenic tyrosine kinase inhibitor

(Chemical Equation Presented). An efficient synthesis of the potent KDR inhibitor 3-[5-[[4-(methylsulfonyl)-1-piperazinyl]methyl]-1H-indole-2-yl] quinolin-2(1H)-one (1) is described. The process features a noncryogenic indole boronation and a dicyclohexylamine-mediated Suzuki coupling.

Electrochemical-Oxidation-Promoted Direct N-ortho-Selective Difluoromethylation of Heterocyclic N-Oxides

An efficient and green electrochemical N-ortho-selective difluoromethylation method of various quinoline and isoquinoline N-oxides has been developed. In this method, sodium difluoromethanesulfinate (HCF2SO2Na) was used as the source of the difluoromethyl moiety, and various N-ortho-selective difluoromethylation quinoline and isoquinoline N-oxides were obtained in good to excellent yields under a constant current. In addition, the reaction was easy to scale up and maintained a good yield. Preliminary mechanism studies suggested that the reaction undergoes a free-radical addition and hydrogen elimination pathway.

Enantioselective Synthesis of Diaryl Sulfoxides Enabled by Molecular Recognition

The enantioselective sulfoxidation of diaryl-type sulfides was accomplished using a chiral manganese porphyrin complex equipped with a remote molecular recognition site. Despite the marginal size difference between the two substituents at the prostereogen

Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions

An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) and a silver-based catalyst system. Key to the success of the reaction is the use of a chiral phenanthroline ligand with a hydrogen bonding site. The enantioselectivity does not depend on the size of the two substituents at the sulfur atom but only on the binding properties of the heterocyclic lactams. A total of 21 chiral sulfimides were obtained in high yields (44–99 %) and with significant enantiomeric excess (70–99 % ee). The sulfimidation proceeds with high site-selectivity and can also be employed for the kinetic resolution of chiral sulfoxides. Mechanistic evidence suggests the intermediacy of a heteroleptic silver complex, in which the silver atom is bound to one molecule of the chiral ligand and one molecule of an achiral 1,10-phenanthroline. Support for the suggested reaction course was obtained by ESI mass spectrometry, DFT calculations, and a Hammett analysis.

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.

Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides

Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.

Copper/manganese oxide catalyzed regioselective amination of quinoline N-oxides: An example of synergistic cooperative catalysis

An atom economical and efficient protocol for C-2 amination of quinoline N-oxides using our synthesized recyclable heterogeneous Cu–MnO catalyst has been reported here. Direct C[sbnd]H aminations of heterocyclic N-oxides with secondary amine were carried out under base, and ligand-free conditions in good to excellent yields. The major advantage is that air is used as a sole oxidant and our catalyst is recycled several times.

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.

Co(III)-Catalyzed C-H Amidation of Nitrogen-Containing Heterocycles with Dioxazolones under Mild Conditions

A cobalt(III)-catalyzed C-8 selective C-H amidation of quinoline N-oxide using dioxazolone as an amidating reagent under mild conditions is disclosed. The reaction proceeds efficiently with excellent functional group compatibility. The utility of the current method is demonstrated by gram scale synthesis of C-8 amide quinoline N-oxide and by converting this amidated product into functionalized quinolines. Furthermore, the developed catalytic method is also applicable for C-7 amidation of N-pyrimidylindolines and ortho-amidation of benzamides.

Cobalt-Catalyzed C8-Dienylation of Quinoline-N-Oxides

An efficient Cp*CoIII-catalyzed C8-dienylation of quinoline-N-oxides was achieved by employing allenes bearing leaving groups at the α-position as the dienylating agents. The reaction proceeds by CoIII-catalyzed C?H activation of qui