1128-61-6

Usage

Uses

Used in Pharmaceutical Industry:
6-Fluoroquinaldine is used as a key intermediate for the synthesis of fluoroquinolones, which are a class of antibacterial agents. The hydrogenation product of 6-fluoro-2-methylquinoline, a derivative of 6-Fluoroquinaldine, plays a crucial role in the development of these potent antibiotics.
Used in Medical Applications:
6-Fluoroquinaldine is also utilized as a highly potent thrombin receptor antagonist. Thrombin receptor antagonists are essential in the treatment of various medical conditions, such as deep vein thrombosis, pulmonary embolism, and acute coronary syndrome, by inhibiting the action of thrombin, a key enzyme in the blood clotting process.

InChI:InChI=1/C10H8FN/c1-7-2-3-8-4-5-9(11)6-10(8)12-7/h2-6H,1H3

Upstream product

• 199186-69-1 (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 
• 64-17-5 ethanol 
• 371-40-4 4-fluoroaniline 
• 1253423-94-7 C₁₁H₁₁FN₂O₅ 
• 350-46-9 4-Fluoronitrobenzene 
• 42835-89-2 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline 
• 15912-68-2 6-fluoro-2-methylquinolin-4-ol 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 332-07-0 bis-(4-fluorophenyl)diazene 
• 109-92-2 ethyl vinyl ether 
• 123-73-9 trans-Crotonaldehyde 
• 872-36-6 vinylene carbonate 
• 67-64-1 acetone 
• 748805-85-8 (2-amino-5-fluorophenyl)methanol 

Downstream Products

• 83719-95-3 2-(6-fluoroquinolin-2-yl)-1-phenylethanone 
• 260430-93-1 6-fluoro-quinoline-2-carbaldehyde 
• 199186-69-1 (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 
• 199186-68-0 (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 
• 124858-35-1 nadifloxacin 
• 79085-71-5 5-bromo-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 
• 79644-90-9 9-Fluoro-5-methyl-8-(4-methyl-1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzoquinolizine-2-carboxylic acid 
• 91-63-4 2-methylquinoline 
• 80290-18-2 5-bromo-6-fluoro-2-methylquinoline 
• 1220450-27-0 2-methyl-6-(4-tolyl)quinoline 
• 1404093-45-3 2‐(6‐fluoroquinolin‐2‐yl)‐1‐(4-nitrophenyl)ethan‐1‐ol 

Relevant academic research and scientific papers

Unusual phenomena during the resolution of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ): Thermodynamic-kinetic control

6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ) was resolved in several different solvents by tartaric acid derivatives as the most common acidic resolving agents available in industrial quantities. Strong reaction kinetics and solvent dependence wer

Synthesis and antifungal activity of diverse C-2 pyridinyl and pyridinylvinyl substituted quinolines

Diverse 2-pyridinyl quinolines 6-12 and 2-pyridinilvinyl quinolines 13-17 were prepared using a straightforward synthesis based on the BiCl 3-catalyzed multicomponent imino Diels-Alder (imino DA) reaction or a novel tandem imino DA/catalytic tetrahydroquinoline ring oxidation/Perkin condensation sequential process. All members of the series showed activities against dermatophytes and some of them possessed a broad spectrum of action. 2-(Pyridin-4-yl)quinoline 9 and 2-(2-pyridin-4-yl)vinyl)quinoline 16 showed the best MIC80 and MIC50 against the clinically important fungi Candida albicans and non-albicans Candida species. In turn, 6-ethyl-2-(pyridin-2-yl)quinoline 6 showed the best properties against standardized as well as clinical strains of Cryptococcus neoformans.

Cooperative Lewis Acid Catalysis for the Enantioselective C(sp3)-H Bond Functionalizations of 2-Alkyl Azaarenes

Herein, we describe the enantioselective C(sp3)-H bond functionalizations of 2-alkyl azaarenes using a cooperative dual Lewis acid catalysis. An achiral Lewis acid activates the unactivated azaarene partner without the need for a strong base. Orthogonally, a chiral-at-metal Lewis acid catalyst enables LUMO lowering and induces chirality. This method tolerates a range of complex molecular scaffolds and exhibits good to excellent yields and selectivity while accepting a wide variety of functional groups.

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen

The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.

Rhodium-Catalyzed C-H Annulation of Free Anilines with Vinylene Carbonate as a Bifunctional Synthon

Chemical transformation with vinylene carbonate as an emerging synthetic unit has recently attracted considerable attention. This report is a novel conversion pattern with vinylene carbonate, in which such a vibrant reagent unprecedentedly acts as a difunctional coupling partner to complete the C-H annulation of free anilines. From commercially available substrates, this protocol leads to the rapid construction of synthetically versatile 2-methylquinoline derivatives (43 examples) with excellent functionality tolerance.

Half-Sandwich Ruthenium Complexes for One-Pot Synthesis of Quinolines and Tetrahydroquinolines: Diverse Catalytic Activity in the Coupled Cyclization and Hydrogenation Process

Four types of half-sandwich ruthenium complexes with an N,O-coordinate mode based on hydroxyindanone-imine ligands have been prepared in good yields. These stable ruthenium complexes exhibited high activity in the catalytic synthesis of quinolines from the reactions of amino alcohols with different types of ketones or secondary alcohols under very mild conditions. Moreover, the methodology for the direct one-pot synthesis of tetrahydroquinoline derivatives from amino alcohols and ketones has been also developed on the basis of the continuous catalytic activity of this ruthenium catalyst in the selective hydrogenation of the obtained quinoline derivatives with a low catalyst loading. The corresponding products, quinolines and tetrahydroquinoline derivatives, were afforded in good to excellent yields. The efficient and diverse catalytic activity of these ruthenium complexes suggested their potential large-scale application. All of the ruthenium complexes were characterized by various spectroscopies to confirm their structures.

Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation

The α7 nicotinic acetylcholine receptor (α7 nAChR) has emerged as a promising therapeutic target for schizophrenia. In our previous work, a novel series of α7-nAChR agonists bearing scaffold of indolizine were discovered. To explore the effect of aromaticity on the activity and find more active agents, herein, fused heterocyclic carboxamide derivatives were designed and synthesized in this study. Based on the evaluation by two-electrode voltage clamp in Xenopus oocytes, 27 of the synthesized compounds showed obvious agonism of α7 nAChR. Particularly, compounds 10a and 10e showed significantly higher Emax than EVP-6124. The result illustrated the importance of aromaticity to the activity of agonism. Compound 10a, which showed EC50 of 1.88 μM and Emax of 72.4%, was further characterized comprehensively, including co-application with type II positive allosteric modulator PNU-120596, selectivity with other closely related ligand-gated ion channel, etc. The results showed that 10a showed moderate selectivity over other subtypes such as α4β2 and α3β4 nAChR. 10a evoked α7-like currents that were inhibited by MLA and enhanced in the presence of the α7 PAM PNU-120596. The analysis of binding mode and understanding of structure-activity relationship provided insights to develop more potent novel α7-nAChR agonists.

Deracemization of Phenyl-Substituted 2-Methyl-1,2,3,4-Tetrahydroquinolines by a Recombinant Monoamine Oxidase from Pseudomonas monteilii ZMU-T01

A monoamine oxidase (MAO5) from Pseudomonas monteilii ZMU-T01 was first heterologously expressed in Escherichia coli BL21(DE3) and then used as a biocatalyst for the deracemization of racemic 2-methyl-1,2,3,4-tetrahdroquinoline derivatives to yield the unreacted R enantiomer with up to >99 % ee. Sequence alignment revealed that MAO5 shared 14.7 % identity toward the well-studied monoamine oxidase (MAO-N).

Acceptorless Dehydrogenation of N-Heterocycles and Secondary Alcohols by Ru(II)-NNC Complexes Bearing a Pyrazoyl-indolyl-pyridine Ligand

Ruthenium(II) hydride complexes bearing a pyrazolyl-(2-indol-1-yl)-pyridine ligand were synthesized and structurally characterized by NMR analysis and X-ray single crystal crystallographic determinations. These complexes efficiently catalyzed acceptorless dehydrogenation of N-heterocycles and secondary alcohols, respectively, exhibiting highly catalytic activity with a broad substrate scope. The present work has established a strategy to construct highly active transition metal complex catalysts and provides an atom-economical and environmentally benign protocol for the synthesis of aromatic N-heterocyclic compounds and ketones.

H-phosphonate mediated sulfonylation of 2-substituted quinoline N-oxides: One-pot strategy for the synthesis of 3/4-sulfonylquinoline derivatives

series of biologically important 3/4-sulfonylquinoline derivatives was synthesized starting from easily available sodium benzenesulfinates, diethyl H-phosphonate and 2-substituted quinoline N-oxides in onepot under metal-free conditions. H-phosphonate plays a decisive role in activating the C3-H, C4-H bonds of the 2-substituted quinoline N-oxides. The isolated 3/4-sulfonylquinolines were characterized by 1H, 13CNMR spectroscopy and HR MS.