177478-49-8

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,4-Tetrahydro-quinoline-6-carboxylic acid methyl ester is used as a key intermediate in the synthesis of new drugs for various therapeutic applications. Its structural properties enable it to form interactions with biological targets, contributing to the development of innovative pharmaceuticals.
Used in Organic Chemistry:
1,2,3,4-Tetrahydro-quinoline-6-carboxylic acid methyl ester serves as a building block for the synthesis of a variety of organic compounds. Its versatile chemical structure allows for further functionalization and modification, facilitating the creation of new molecules with potential applications in various fields.
Used in Drug Discovery and Development Research:
Due to its potential biological activities, 1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester is utilized in drug discovery and development research. Its ability to interact with biological targets makes it a valuable compound for exploring new therapeutic avenues and advancing the understanding of disease mechanisms.

InChI:InChI=1/C11H13NO2/c1-14-11(13)9-4-5-10-8(7-9)3-2-6-12-10/h4-5,7,12H,2-3,6H2,1H3

Upstream product

• 35387-93-0 3-iodo-4-methoxy-benzoic acid methyl ester 
• 38896-30-9 6-(methoxycarbonyl)quinoline 
• 10349-57-2 Quinoline-6-carboxylic acid 
• 67-56-1 methanol 
• 5382-49-0 1,2,3,4-tetrahydroquinoline-6-carboxylic acid 
• 177478-63-6 2-oxo-1,2,3,4-tetrahydro-6-quinolinecarboxylic acid methyl ester 
• 157-22-2 diazirine 
• 186581-53-3 diazomethane 

Downstream Products

• 1312158-51-2 C₁₈H₁₇NO₃ 
• 1312158-46-5 C₁₈H₁₇NO₃ 
• 1312158-53-4 C₁₇H₁₅NO₃ 

Relevant academic research and scientific papers

Engineering the geometric and electronic structure of Ru: Via Ru-TiO2interaction for enhanced selective hydrogenation

Modulation of the metal-support interaction plays a key role in many important chemical reactions. Here, by adjusting the reduction method of the catalyst and introducing oxygen vacancies in TiO2 to regulate the interaction between Ru and TiO2, four supported Ru nanocatalysts with different encapsulation degrees and electronic structures were obtained. Ru nanoparticles (NPs) partially encapsulated by TiO2 can achieve the selective hydrogenation of 6-chloroquinoline even at room temperature, with a TOF of 12 h-1. Catalytic characterization and DFT calculations indicated that partially encapsulated Ru NPs not only provided active sites for H2 dissociation, but also reduced the probability of Ru NPs being poisoned. Meanwhile, the oxygen vacancies on the surface of TiO2 can adsorb 6-chloroquinoline molecules and provide additional active sites for hydrogenation via hydrogen spillover. Moreover, the enhanced electron transfer from oxygen-deficient TiO2 to Ru made Ru electron-rich, which repelled C-Cl bonds and effectively prevented the production of dechlorination products. This journal is

Method for selective catalytic hydrogenation of aromatic heterocyclic compounds in non-hydrogen participation manner

The invention discloses a method for selective catalytic hydrogenation of aromatic heterocyclic compounds in a non-hydrogen participation manner. The method comprises the following steps: by taking 1, 5-cyclooctadiene iridium chloride dimer as a catalyst and phenylsilane as a hydrogen source, carrying out stirring reaction under mild conditions without adding a ligand, namely catalytically hydrogenating the aromatic heterocyclic compounds to obtain hydrogenated products of the aromatic heterocyclic compounds. The method has the advantages of low cost, mild reaction conditions, high selectivity and the like, and special equipment such as a high-pressure kettle and the like and high-temperature conditions which are required when hydrogen is used are avoided.

Tuning the Catalytic Performance of Cobalt Nanoparticles by Tungsten Doping for Efficient and Selective Hydrogenation of Quinolines under Mild Conditions

Non-noble bimetallic CoW nanoparticles (NPs) partially embedded in a carbon matrix (CoW@C) have been prepared by a facile hydrothermal carbon-coating methodology followed by pyrolysis under an inert atmosphere. The bimetallic NPs, constituted by a multishell core-shell structure with a metallic Co core, a W-enriched shell involving Co7W6 alloyed structures, and small WO3 patches partially covering the surface of these NPs, have been established as excellent catalysts for the selective hydrogenation of quinolines to their corresponding 1,2,3,4-tetrahydroquinolines under mild conditions of pressure and temperature. It has been found that this bimetallic catalyst displays superior catalytic performance toward the formation of the target products than the monometallic Co@C, which can be attributed to the presence of the CoW alloyed structures.

Homogeneous pressure hydrogenation of quinolines effected by a bench-stable tungsten-based pre-catalyst

We report on an operationally simple catalytic method for the tungsten-catalyzed hydrogenation of quinolines through the use of the easily handled and self-contained precursor [WCl(η5-Cp)(CO)3]. This half sandwich complex is indefinitely storable on the bench in simple screw-capped bottles or stoppered flasks and can, if required, be prepared on a multi-gram scale while the actual catalytic transformations were performed in the presence of a Lewis acid in order to achieve both decent substrate conversions and product yields. The described method represents a facile and atom-efficient access to a variety of 1,2,3,4-tetrahydroquinolines that circumvents the use of cost-intensive and oxygen-sensitive phosphine ligands as well as auxiliary hydride reagents.

Utilization of renewable formic acid from lignocellulosic biomass for the selective hydrogenation and/or N-methylation

Lignocellulosic biomass is one of the most abundant renewable sources in nature. Herein, we have developed the utilization of renewable formic acid from lignocellulosic biomass as a hydrogen source and a carbon source for the selective hydrogenation and further N-methylation of various quinolines and the derivatives, various indoles under mild conditions in high efficiencies. N-methylation of various anilines is also developed. Mechanistic studies indicate that the hydrogenation occurs via a transfer hydrogenation pathway.

Geometric and electronic effects on the performance of a bifunctional Ru2P catalyst in the hydrogenation and acceptorless dehydrogenation of N-heteroarenes

The development of bifunctional catalysts for the efficient hydrogenation and acceptorless dehydrogenation of N-heterocycles is a challenge. In this study, Ru2P/AC effectively promoted reversible transformations between unsaturated and saturated N-heterocycles affording yields of 98% and 99%, respectively. Moreover, a remarkable enhancement in the reusability of Ru2P/AC was observed compared with other Ru-based catalysts. According to density functional theory calculations, the superior performance of Ru2P/AC was ascribed to specific synergistic factors, namely geometric and electronic effects induced by P. P greatly reduced the large Ru-Ru ensembles and finely modified the electronic structures, leading to a low reaction barrier and high desorption ability of the catalyst, further boosting the hydrogenation and acceptorless dehydrogenation processes.

Encapsulating Cobalt into N-Doping Hollow Frameworks for Efficient Cascade Catalysis

The development of nonprecious catalysts for hydrogenation of organic molecules is of great importance in heterogeneous catalysis. Herein, we report a series of N-doped hollow carbon frameworks encompassing cobalt nanoparticles (denoted as Co@NHF-900) constructed as a new kind of reusable catalyst for this purpose by pyrolysis of ZIF-8@Co-dopamine under Ar atmospheres. Notably, the framework of ZIF-8 is essential for efficient catalyst by providing a carbon framework to support Co-dopamine. The experimental results reveal that the ZIF-8 renders a large hollow place within the catalysts, allowing the enrichment of the substrate and windows of the hollow structure and the ease of mass transfer of products during the reaction. All of the virtues made Co@NHF-900 a good candidate for hydrogenation of quinolines with high activity (TOF value of 119 h-1, which is several times than that of akin catalysts) and chemoselectivity.

Cu-Catalyzed Chemoselective Reduction of N-Heteroaromatics with NH3·BH3 in Aqueous Solution

An efficient catalytic system was successfully developed on reduction of N-heteroaromatics with H3N?BH3 as hydrogen source in CuSO4 solution, featuring excellent chemoselectivity as well as very broad functional group tolerance. Various challenging substrates, such as OH-, NH2-, Cl-, Br-, etc., contained quinolines, quinoxalines, 1,5-naphthyridines and quinazolines were all reduced smoothly. Mechanistic studies suggested that [Cu-H] intermediate might be generated from NH3?BH3, which was believed to form with H3N?BH3 in CuSO4 solution.

Cu Nanoclusters Anchored on the Metal-Organic Framework for the Hydrolysis of Ammonia Borane and the Reduction of Quinolines

Free-access active sites created and the interaction regulated between them and substrates during the heterogeneous catalysis process are crucial, which remain a great challenge. In this work, in suit reduced to afford naked Cu nanoparticles (NPs) have been anchored on the metal-organic framework (MOF), NH2-MOF, to form Cu-NH2-MOF. The strategy can precisely control the Cu NP formation with small size and uniform distribution. The Cu NP properties and MOF advantages have been integrated to create a great catalyst with multiple functions and have resulted in improving the recyclability and superb catalytic activity for the one-pot reduction of heterocycle reactions under mild conditions. The experimental and theoretical calculation results show that the superior performance should be attributed to the framework of NH2-MOF that provides large caves for substrate enrichment and the stabilization of Cu sites by the -NH2 group.

Visible light-mediated Smiles rearrangements and annulations of non-activated aromatics

We report the first examples of radical cation Smiles rearrangements. A series of aryloxy alkylamines underwent spontaneous reaction, with the amino group displacing theipso-alkoxy group through substitution, at ambient temperature and under photoactivation by visible light in the presence of an acridinium catalyst (5 mol%). The study was extended to 3-(2-methoxyphenyl)propan-1-amine derivatives, which lack an appropriateipsoleaving group. Here, efficient cyclisations resulted in displacement of the methoxy group and formation of tetrahydroquinolines.