24641-30-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-M-Tolyl-quinoline is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals for its ability to contribute to the development of new drugs and pesticides. Its unique chemical structure allows it to be a versatile building block in organic synthesis.
Used in Organic Light-Emitting Diodes (OLEDs) Industry:
2-M-Tolyl-quinoline is utilized as a component in the creation of organic light-emitting diodes due to its electronic and optical properties that are beneficial for the performance of OLEDs.
Used in Advanced Materials Industry:
2-M-Tolyl-quinoline also has potential applications in the development of other advanced materials, where its specific chemical and physical attributes can be leveraged to enhance material properties or introduce new functionalities.

Upstream product

• 5344-90-1 2-Aminobenzyl alcohol 
• 585-74-0 3-Methylacetophenone 
• 7287-81-2 1-(m-methylphenyl)ethanol 
• 615-43-0 2-iodophenylamine 
• 29978-38-9 1-(m-tolyl)prop-2-yn-1-ol 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 91-22-5 quinoline 
• 28987-79-3 m-tolylmagnesium bromide 
• 766-82-5 1-ethynyl-3-methyl-benzene 
• 5339-85-5 2-aminophenethyl alcohol 
• 620-23-5 m-tolyl aldehyde 
• 4403-69-4 2-amino-1-benzylamine 
• 3333-20-8 1-allyl-3-methylbenzene 
• 62-53-3 aniline 

Downstream Products

• 93-10-7 quinoline-2-carboxylic acid 
• 1198359-43-1 2-(3-methylphenyl)quinoline hydrochloride 
• 1198359-72-6 2-(3-methylphenyl)quinoline hydrobromide 
• 1159987-36-6 (S)-2-(3-methylphenyl)-1,2,3,4-tetrahydroquinoline 
• 1198359-53-3 (R)-2-(3-methylphenyl)-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines

A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.

Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst

This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.

Ruthenium complex and preparation method thereof and catalytic application

The invention discloses a ruthenium complex and a preparation method thereof and catalytic application. The ruthenium complex is reported for the first time. Research finds that the ruthenium complexhas the activity of catalytically synthesizing quinazoline and derivatives thereof or catalytically synthesizing quinoline and derivatives thereof. When the ruthenium complex provided by the inventionis used for catalytic synthesis of quinazoline and derivatives thereof or quinoline and derivatives thereof, the ruthenium complex has the advantages of mild reaction conditions, wide substrate range, high catalytic product yield and good functional group tolerance, and is significantly superior to the prior art.

A cobalt-catalyzed method for synthesizing quinoline and quinazoline compounds

The present invention discloses a cobalt-catalyzed synthesis of quinoline and quinazoline compounds, by a benzene compound with amino and hydroxyl groups or benzonitrile compounds as raw materials, in the presence of a catalyst and a base by a receptor-fr

The preparation of a Co@C3N4catalyst and applications in the synthesis of quinolines from 2-aminobenzyl alcohols with ketones

An unsymmetrical diphenylphosphino-pyridinyl-triazole ligand was synthesized and characterized through IR, NMR and MS and the corresponding earth-abundant metal complex (cobalt) was prepared. Considering energy consumption and environmental friendliness, it is necessary to turn this diphenylphosphino-pyridinyl-triazole cobalt complex into a recyclable catalyst, which could easily be reused. Therefore, a heterogeneous catalyst was synthesized through Co-doping of C3N4, and the Co-nanoparticles on C3N4revealed high catalytic activity for the synthesis of quinolines with good recovery performance.

Efficient access to quinolines and quinazolines by ruthenium complexes catalyzed acceptorless dehydrogenative coupling of 2-aminoarylmethanols with ketones and nitriles

Treatment of N,N,O-tridentate pyrazolyl-pyridinyl-alcohol ligands, 2-(CR1R2OH)-6-[3,5-(R3)2C3HN2]C5H3N (R1 = R2 = Me, R3 = H (L1H); R1 = Me, R2 = Ph, R3 = H (L2H); R1 = R2 = Ph, R3 = H (L3H); R1 = R2 = R3 = Me (L4H)) with RuCl3?xH2O in refluxing EtOH afforded the corresponding Ru(III) complexes L2RuCl (1a-1d), which were well characterized by IR, HR-MS and X-ray single crystal structural determination. These Ru complexes showed similarly high catalytic performance for both dehydrogenative couplings of 2-aminoarylmethanols with ketones and nitriles, giving the quinolines and quinazolines in good to excellent yields. This protocol provides an atom-economical and sustainable route to access various structurally important quinoline and quinazoline derivatives by using phosphine-free ligand based Ru catalysts.

Asymmetric Synthesis of Hydroquinolines with α,α-Disubstitution through Organocatalyzed Kinetic Resolution

The first kinetic resolution of hydroquinoline derivatives with α,α-disubstitution has been achieved through asymmetric remote aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. Mechanistic studies suggest a monomeric catalyst pathway proceeding through rate- and enantio-determining electrophilic attack promoted by a network of attractive non-covalent interactions between the substrate and catalyst. Facile subsequent removal and transformations of the newly introduced hydrazine moiety enable these protocols to serve as powerful tools for asymmetric synthesis of N-heterocycles with α,α-disubstitution.

Kinetic Resolution of 2,2-Disubstituted Dihydroquinolines through Chiral Phosphoric Acid-Catalyzed C6-Selective Asymmetric Halogenations

A novel kinetic resolution of 2,2-disubstituted dihydroquinolines was achieved by regioselective asymmetric halogenations enabled by chiral phosphoric acid catalysis. A series of dihydroquinolines bearing 2,2-disubstitutions were well-tolerated in these reactions, generating both the recovered dihydroquinolines and C-6-brominated products with high enantioselectivities, with s-factors up to 149. In addition, this kinetic resolution protocol is also applicable for 2,2-disubstituted tetrahydroquinoline and asymmetric iodonation reaction.

Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes

The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.

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.