3297-76-5

Usage

Core structure

Tetrahydroquinoline core, which is a cyclic compound consisting of a six-membered ring with four carbon atoms and two additional carbon atoms attached to it.

Substituent

A phenyl group, which is a six-membered aromatic ring with six carbon atoms and one hydrogen atom, is attached to the tetrahydroquinoline core.

Bicyclic structure

The compound has a unique bicyclic structure, with the phenyl group and the tetrahydroquinoline core forming two interconnected rings.

Application in organic synthesis

1-Phenyl-1,2,3,4-tetrahydroquinoline is commonly used as a building block for the synthesis of various pharmaceuticals and biologically active compounds.

Diverse applications

The compound has a wide range of applications, including its use in the synthesis of pharmaceuticals, biologically active compounds, and as a potential antiviral and antifungal agent.

Biological and pharmacological activities

1-Phenyl-1,2,3,4-tetrahydroquinoline has been studied for its potential biological and pharmacological activities, particularly its role as a potential antiviral and antifungal agent.

Value in the field of chemistry and pharmaceuticals

The compound is considered valuable due to its versatile applications and its importance in the synthesis of various pharmaceuticals and biologically active compounds.

Upstream product

• 104636-55-7 1-phenyl-1-(3-phenylpropyl)hydrazine 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 108-86-1 bromobenzene 
• 108-90-7 chlorobenzene 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 89-98-5 2-chloro-benzaldehyde 
• 2039-88-5 2-bromostyrene 
• 100-61-8 N-methylaniline 
• 103391-83-9 N-(2-(2-chlorophenyl)propyl)aniline 
• 2039-87-4 2-chlorostyrene 
• 108-95-2 phenol 
• 2142-69-0 2-bromophenyl methyl ketone 
• 491-34-9 N-methyl-1,2,3,4-tetrahydroquinoline 

Downstream Products

• 1443380-76-4 C₂₃H₂₉N₃O₄ 
• 1443380-47-9 N-phenyl-2-(1,2-di-tert-butoxycarbonylhydrazino)-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Tandem Reaction of Arynes with Tertiary Amines and Aldehydes: Formation of 9- and 10-Membered Dibenzo[1,5]oxaza Heterocycles

The aryne-mediated three-component reaction of arynes, tertiary amines, and aldehydes followed by intramolecular nucleophilic aromatic substitution afforded novel 9- and 10-membered heterocycles. Thus, the reaction of 2-(trimethylsilyl)phenyl triflate with N-phenylmorpholine and benzaldehyde in the presence of CsF gave o-morpholinobenzhydryl phenyl ether in 76 % yield. By using N-methylindoline, nine-membered dibenzo[1,5]oxazonines were synthesized in moderate yields. The aryne-mediated three-component reaction of arynes, tertiary amines, and aldehydes followed by intramolecular nucleophilic aromatic substitution affords 9- and 10-membered heterocycles. Thus, the reaction of 2-(trimethylsilyl)phenyl triflate with N-methylindoline and aldehydes in the presence of CsF gives dibenzo[1,5]oxazonines in moderate yields; 18-C-6 = 18-crown-6.

A facile route for the preparation of N-phenyl tetrahydroquinolines and tetrahydroisoquinolines

A convenient N-arylation of tetrahydroquinoline and tetrahydroisoquinoline is described using electron-poor, electron-neutral, or electron-rich arylhalide derivatives and palladium(II)-BINAP as a catalyst.

Double Ligands Enabled Ruthenium Catalyzed ortho-C?H Arylation of Dialkyl Biarylphosphines: Straight and Economic Synthesis of Highly Steric and Electron-Rich Aryl-Substituted Buchwald-Type Phosphines

A double-ligands enabled ruthenium catalyzed C(sp2)?H arylation of dialkyl phosphines is described, which provides a straight access to aryl-substituted dialkyl phosphine ligands. The combination of 1,3-diketone and amino acid ligands is essential for this transformation. An important six-membered cycloruthenium intermediate was successfully isolated and characterized by X-ray diffraction. Mechanistic studies showed that the 1,3-diketone promoted the process of oxidative addition of cycloruthenium intermediate. Some of modified CyJohnPhos ligands exhibited highly catalytic activity in palladium catalyzed C?N bond formation. (Figure presented.).

Two-Step Procedure for the Synthesis of 1,2,3,4-Tetrahydro-quinolines

A new two-step procedure that includes an initial regioselective intermolecular hydroaminoalkylation of ortho-chlorostyrenes with N-methylanilines and a subsequent intramolecular Buchwald–Hartwig amination gives direct access to 1,2,3,4-tetrahydroquinolines. The hydroaminoalkylation reaction of the ortho-chlorostyrenes is catalyzed by a 2,6-bis(phenylamino)pyridinato titanium complex which delivers the linear regioisomers with high selectivities. In addition, the formation of unexpected dihydroaminoalkylation products from styrenes and N-methylanilines is reported.

The impact of the nature of amine reactants in the palladium catalyzed conversion of phenol to N-substituted anilines

Anilines and cyclohexylamines are currently produced from fossil feedstocks. Phenol would be an attractive alternative feedstock that can be obtained from renewable resources. We herein clarify the influence of the amine on the course of the amination of phenol using a hydrogen borrowing strategy. Amines can in this case act as a reductant which can be dehydrogenated to initiate the partial hydrogenation of phenol which is required for the reaction to take place. The nature of the amine reactant can have a larger effect than the presence of additional reductants like sodium formate. The results in this report do not only present a method for the amination of phenol without addition of an extra reductant, but also rationalize the reactivity of amines in their reaction with phenol.

Potassium tert-butoxide-mediated generation of arynes from o-bromoacetophenone derivatives

o-bromoacetophenone derivatives as new versatile aryne precursors are induced to selectively eliminate the CAr–Br and CAr–C(Ac) bonds in the help of t-BuOK. Furthermore, the active aryne intermediates are successfully appl

Palladium-catalyzed amination of aryl sulfoxides

Amination of diaryl sulfoxides with anilines and alkylamines has been accomplished under palladium/N-heterocyclic carbene (NHC) catalysis. Owing to its electron deficiency, the leaving arenesulfenate anion would be smoothly released from the palladium center to result in uneventful catalyst turnover under milder reaction conditions in comparison with previous C-S bond amination reactions. This amination accommodated a wider range of functional groups such as silyl, boryl, methylsulfanyl, and halogen moieties. Regioselective amination of unsymmetrical diaryl sulfoxides was also executed by means of steric bias.

Direct Acylation of C(sp3)-H Bonds Enabled by Nickel and Photoredox Catalysis

Using nickel and photoredox catalysis, the direct functionalization of C(sp3)-H bonds of N-aryl amines by acyl electrophiles is described. The method affords a diverse range of α-amino ketones at room temperature and is amenable to late-stage coupling of complex and biologically relevant groups. C(sp3)-H activation occurs by photoredox-mediated oxidation to generate α-amino radicals which are intercepted by nickel in catalytic C(sp3)-C coupling. The merger of these two modes of catalysis leverages nickel's unique properties in alkyl cross-coupling while avoiding limitations commonly associated with transition-metal-mediated C(sp3)-H activation, including requirements for chelating directing groups and high reaction temperatures. Teamwork: The direct functionalization of C(sp3)-H bonds of N-aryl amines by acyl electrophiles is achieved, thus affording a diverse range of α-amino ketones at room temperature. C(sp3)-H activation occurs by photoredox-mediated oxidation to generate α-amino radicals which are intercepted by nickel in catalytic C(sp3)-C coupling.

Palladium-catalyzed amination of aryl sulfides with aliphatic amines

Conditions for the palladium-NHC-catalyzed amination of aryl sulfides with aliphatic as well as aromatic amines were established. The KHMDS-mediated amination of heteroaryl sulfides could proceed without palladium. Based on the distinct difference in reactivity of C-Br and C-S bonds, a sequential amination of bromothioanisole can take place to install two different alkylamino groups onto the aromatic ring in one pot. A palladium-NHC precatalyst shows high efficiency for C-S bond cleavage for the amination of aryl sulfides with aliphatic amines or aromatic amines.

A visible-light-mediated synthesis of carbazoles

The photosynthetic preparation of N-aryl- and N-alkyl-bearing carbazoles utilizes continuous flow, visible light, and an in situ formed Cu-based sensitizer (see picture). The method is mild and efficient, and allows the straightforward synthesis of a variety of carbazoles with different substituents, heterocycles, and complex carbon architectures. Copyright