27623-83-2

Usage

Chemical Family

Quinoline family
Bicyclic compound with a quinoline ring fused to a tetrahydroquinoline ring

Structure

1-methyl-4-phenyl substitution
A methyl group attached to the 1-position and a phenyl group attached to the 4-position of the tetrahydroquinoline ring

Molecular Weight

Not provided in the material
Can be calculated based on the molecular formula (C16H15NO)

Potential Use

Neuroprotective agent
Commonly used in research and drug discovery, particularly in the context of Parkinson's disease

Relevance

Understanding neurodegenerative diseases and developing therapeutic treatments
The compound's structure and properties make it a subject of interest for studying and treating conditions like Parkinson's disease

Upstream product

• 30290-78-9 4-phenyl-1,2,3,4-tetrahydroquinoline 
• 74-88-4 methyl iodide 
• 100-42-5 styrene 
• 13657-45-9 N-methyl-N-(methoxymethyl)-aniline 
• 146041-91-0 1-methyl-4-(benzotriazol-N-yl)-1,2,3,4-tetrahydroquinoline 
• 10482-83-4 o-(1-phenylvinyl)-N,N-dimethylaniline 
• 3056-73-3 N-phenylcinnamamide 
• 62-53-3 aniline 
• 4888-33-9 4-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 102-92-1 Cinnamoyl chloride 
• 33603-47-3 (E)-N-methyl-N-phenyl-3-phenyl-2-propenylamine 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 605-03-8 4-phenylquinoline 
• 100-61-8 N-methylaniline 

Relevant academic research and scientific papers

Practical one-pot procedure for the synthesis of 1,2,3,4- tetrahydroquinolines by the imino-Diels-Alder reaction

A novel-one-pot procedure for the synthesis of tetrahydroquinolines via the imino-Diels-Alder reaction is described. This procedure gives better yields and exhibits better versatility for alkene substrates than the existing hemi-aminal based methodologies

Intramolecular Cyclizations of Vinyl-Substituted N, N-Dialkyl Arylamines Enabled by Borane-Assisted Hydride Transfer

Catalytic amounts of B(C6F5)3 have been found to be able to promote the intramolecular cyclization of vinyl-substituted N,N-dialkyl arylamines to afford nitrogen-containing heterocycles. Our mechanistic studies indicate th

Intermolecular Polar Cycloadditions of Cationic 2-Azabutadienes from Thiomethylamines: A New and Efficient Method for the Regio- and Diastereo-selective Synthesis of 1,2,3,4-Tetrahydroquinolines

Substituted 1,2,3,4-tetrahydroquinolines and related condensed nitrogen-heterocycles are formed highly regio- and diastereo-selectively with yields ranging from 57 to 100percent by intermolecular polar cycloadditions of cationic 2-azabutadienes

Lewis Acid Assisted Reactions of N-(α- Aminoalkyl)benzotriazoles and Unactivated Alkenes for the Facile Synthesis of 4-, 2,4-, and 3,4-Substituted 1,2,3,4-Tetrahydroquinolines

A range of substituted tetrahydroquinolines have been synthesized from benzotriazole derivatives and unactivated alkenes in the presence of a Lewis acid. These reactions utilize readily available starting materials and mild reaction conditions, and give h

One-pot synthesis of tetrahydroquinolines catalyzed by Dy(OTf)3 in aqueous solution

Various 4-substituted-1-methyltetrahydroquinolines are easily accessible from the one-pot condensation reaction of N-methylaniline with commercial formaldehyde solution and electron-rich alkenes in the presence of Dy(OTf)3 (1 mol %) under mild

Radical-mediated direct C-H amination of arenes with secondary amines

Aryl dialkyl amines, valuable subunits of a wide range of effect chemicals, are accessed by intramolecular amination of aromatic C-H bonds employing UV photolysis of N-chloroamines. The reactions show good functional group tolerance and allow access to a range of fused and bridged polycyclic structures. The homogeneous reaction conditions allow for the one-pot conversion of secondary amines to their arylated derivatives. Experimental and theoretical evidence supports the involvement of electrophilic aminium radicals which react via direct ortho-attack on the arene.

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

The synthesis of novel tetrahydroquinolines (THQ) and dihydroquinolines (DHQ) are reported using three practical, scalable synthetic approaches to access highly lipophilic analogues bearing a 6-iodo substituent, each with a different means of cyclisation. A versatile and stable quinolin-2-one intermediate was identified, which could be reduced to the corresponding THQ with borane reagents, or to the DHQ with diisobutylaluminium hydride via a novel elimination that is more favourable at higher temperatures. Coupling these strongly electron-donating scaffolds to electron-accepting moieties caused the resulting structures to exhibit strong fluorescence.

Simple and convenient approach for synthesis of tetrahydroquinoline derivatives and studies on aza-Cope rearrangement

A simple and novel synthesis of 1,2,3,4-tetrahydroquinoline derivatives by polyphosphoric acid-assisted reaction of N-aryl allyl anilines prepared from anilines has been reported. The generality and scope of the approach has been demonstrated by extending it to the synthesis of 1,2,5,6-tetrahydro-4H- pyrrolo[3,2,1-ij]quinoline (lilolidine) and 2,3,6,7-tetrahydro-1H,5H-pyrido[3,2, 1-ij]quinoline (julolidine). Further, Lewis acid- mediated aza-Cope rearrangement of various N-aryl allyl anilines has been demonstrated.

Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with α,β-Unsaturated Ethers. A Novel Route to 1,4- and 1,3-Disubstituted 1,2,3,4-Tetrahydroquinolines

N-Alkyl-N-aryl-1H-benzotriazole-1-methanamines 3, easily accessible from the condensation of anilines with formaldehyde and benzotriazole, undergo acid-catalyzed reactions with ethyl vinyl ether to give 1-alkyl-4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquin

Electroorganic Chemistry. 62. Reaction of Iminium Ion with Nuclophile: A Versatile Synthesis of Tetrahydroquinolines and Julolidines

A versatile synthetic method of tetrahydroquinolines and julolidines has been developed.The method involves the anodic oxidation of N,N-dimethylaniline in methanol to afford α-methoxylated or α,α'-dimethoxylated compounds and subsequent treatment of the products with Lewis acids in the presence of nucleophiles.Simple and electron-rich olefins such as alkenes, styrene, enol ethers, silyl enol ethers, enamines, and enol esters are usable as the nucleophiles.The intermediary formation of iminium ions from the methoxylated compounds is proposed as one of the key steps.The nucleophilic reaction od Grignard reagents with the methoxylated compounds in the presence of Lewis acid is also described.