73987-38-9

Usage

Uses

Used in Pharmaceutical Industry:
QUINOLINE-6-CARBOXYLIC ACID ETHYL ESTER is used as a key intermediate in the synthesis of pharmaceutical compounds for its ability to contribute to the development of anti-malarial drugs and anti-inflammatory agents. Its presence in these formulations aids in enhancing their therapeutic effects and addressing specific medical needs.
Used in Dye and Pigment Production:
In the dye and pigment industry, QUINOLINE-6-CARBOXYLIC ACID ETHYL ESTER serves as a valuable precursor, playing a crucial role in the production of various dyes and pigments. Its chemical properties enable the creation of a wide range of colorants used in different applications, such as textiles, plastics, and printing inks.
Used in Organic Synthesis:
QUINOLINE-6-CARBOXYLIC ACID ETHYL ESTER is utilized in organic synthesis due to its versatility and reactivity, allowing for the creation of a diverse array of chemical products. Its ability to participate in various chemical reactions makes it an essential component in the synthesis of complex organic molecules for a multitude of applications across different industries.

InChI:InChI=1/C12H11NO2/c1-2-15-12(14)10-5-6-11-9(8-10)4-3-7-13-11/h3-8H,2H2,1H3

Upstream product

• 612-57-7 6-chloroquinoline 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 94-09-7 p-aminoethylbenzoate 
• 504-63-2 trimethyleneglycol 
• 110443-51-1 1-oxy-quinoline-6-carboxylic acid ethyl ester 
• 107-18-6 allyl alcohol 
• 15226-74-1 dicobalt octacarbonyl 
• 173089-80-0 quinolin-6-yl triflate 
• 101248-36-6 ethyl 4-(prop-2-ynylamino)benzoate 
• 150-13-0 4-amino-benzoic acid 
• 10349-57-2 Quinoline-6-carboxylic acid 

Downstream Products

• 342908-16-1 2-aminoquinoline-6-carboxylic acid ethyl ester 
• 29969-56-0 2-chloroquinoline-6-carboxylic acid ethyl ester 
• 4113-04-6 quinoline-6-carbaldehyde 
• 858784-67-5 N-(quinoline-6-carbonyl)-N'-(toluene-4-sulfonyl)-hydrazine 
• 849996-80-1 2-chloroquinoline-6-carboxylic acid 
• 5622-38-8 ethyl 6-quinolineacetate 
• 5382-47-8 quinoline-6-carboxylic acid hydrazide 
• 73013-68-0 1-(quinolin-6-yl)ethan-1-one 
• 100516-88-9 6-(hydroxymethyl)quinoline 

Relevant academic research and scientific papers

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions

Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

Imidazopyridine-fused [1,3]diazepinones: modulations of positions 2 to 4 and their impacts on the anti-melanoma activity

A series of 19 novel pyrido-imidazodiazepinones, with modulations of positions 2, 3 and 4 of the diazepine ring were synthesised and screened for their in vitro cytotoxic activities against two melanoma cell lines (A375 and MDA-MB-435) and for their poten

Construction of Esters through Sulfuryl Fluoride (SO 2 F 2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature

A facile method for the construction of esters through dehydrative coupling of carboxylic acids with alcohols is developed. The reactions are mediated by sulfuryl fluoride (SO 2 F 2) at room temperature and proceed with high efficiency. The method has several advantages including broad substrate scope, mild conditions, excellent functional group compatibility and affords high yields, even on gram scale.

From Anilines to Quinolines: Iodide- and Silver-Mediated Aerobic Double C?H Oxidative Annulation–Aromatization

Quinoline synthesis from easily accessible raw materials such as anilines is a valuable and meaningful task. Herein, we communicate an iodide- and silver-mediated C?H/C?H oxidative annulation–aromatization between anilines and allyl alcohols. This protocol provides a direct route to the synthesis of quinoline derivatives from inexpensive commodities. Various kinds of anilines, even heterocyclic anilines, were shown to be workable substrates, generating the corresponding multi-substituted quinolines in good yields.

Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines

An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.

Preparation method of quinoline derivative

The invention provides a preparation method of a quinoline derivative. The method includes the steps of: in the presence of an oxidizing agent, adding a catalyst, then adding aniline or aromatic amine with different substituents, at the same time adding alcohol for reaction so as to prepare the quinoline derivative by one step. Specifically, the catalyst comprises a metal catalyst, an assistant catalyst I and an assistant catalyst II; the metal catalyst is a transition metal catalyst; the assistant catalyst I is an alkaline nitrogen-containing ligand; and the assistant catalyst II is an acidic compound. The quinoline derivative prepared by the method provided by the invention has stable performance and high purity. And the preparation method of the quinoline derivative can prepare quinoline, 2-methylquinoline, 8-hydroxyquinoline quinoline and other derivatives by one-step reaction, and the preparation method is simple and practicable. The preparation process does not produce new "three wastes", is environment-friendly, and provides a green and environment-friendly synthesis method. The preparation method has the characteristics of few raw material variety, little reaction equipment, few preparation step and low cost, and is more suitable for industrial production.

Room Temperature Carbonylation of (Hetero) Aryl Pentafluorobenzenesulfonates and Triflates using Palladium-Cobalt Bimetallic Catalyst: Dual Role of Cobalt Carbonyl

An efficient method for the carbonylation of (hetero) aryl pentafluorobenzenesulfonates and triflates under exceptionally mild conditions using palladium/dicobalt octacarbonyl [Pd/Co2(CO)8] has been developed. Besides acting as carbon monoxide (CO) source, Co2(CO)8enhances the reaction rate by accelerating the CO insertion through an in situ generated bimetallic palladium cobalt tetracarbonyl [Pd-Co(CO)4] complex. Under the optimized reaction condition, carbonylation of a wide range of activated and deactivated, as well as sterically hindered and heteroaromatic, substrates proceeded efficiently at room temperature. The high chemoselectivity and improved synthesis of biologically relevant Isoguvacine and Lazabemide intermediates highlights its scope as a valuable synthetic method. The generality of this protocol was further extended to other electrophiles (bromides, chlorides and tosylates). (Figure presented.).

Synthesis of naphthalene ring derivatives and Benzoheterocycles the method of the compound

The invention discloses a method for synthesizing naphthalene derivative and benzo-heterocycle compounds. The method is realized by promoting a reaction similar to Mortia-Baylis-Hillman between aryl aldehyde having alpha, beta-unsaturated ester on ortho-position and ketone compounds under the catalysis action of tertiary amine and tertiary phosphine organic small molecular catalysts, so as to remove a molecule of H2O, so that the naphthalene derivative or benzo-heterocycle compounds are generated. The method disclosed by the invention is simple in operation step, cheap and easily available in adopted catalysts and harmless to environment, and a series of naphthalene derivative and benzo-heterocycle compounds are synthesized with relatively high yield.