71858-10-1

Upstream product

• 3246-78-4 N-(4-methoxybenzylidene)-4-methylaniline 
• 536-74-3 phenylacetylene 
• 106-49-0 p-toluidine 
• 123-11-5 4-methoxy-benzaldehyde 
• 49634-76-6 1-phenyl-1-(2-amino-5-methylphenyl)ethylene 
• 39212-13-0 (E)-1-phenyl-3-(4-methoxyphenyl)prop-2-en-1-ol 
• 98-86-2 acetophenone 
• 16616-43-6 1-(4-methoxy-phenyl)-3-phenyl-propynone 

Relevant academic research and scientific papers

A method for utilizing the aromatic amine, aromatic aldehyde, synthesized of quinoline derivatives

The invention provides a method for synthesizing a quinoline derivative by utilizing arylamine, aromatic aldehyde and ketone, and belongs to the technical field of the synthesis of the quinoline derivative. According to the method for synthesizing a quinoline derivative by utilizing arylamine, aromatic aldehyde and ketone, in the existence of silver trifluoromethanesulfonate and trifluoromethanesulfonic acid, the quinoline derivative is synthesized by virtue of the reaction of an arylamine compound, an aromatic aldehyde compound and ketone compound. A reaction general formula is as shown in the specification. Compared with the prior art, the method is not only applicable to a great amount of functional groups, but also is simple in operation, high in yield, single in product structure, convenient to separate and purify, safe, low in price and small in pollution.

Silver-catalyzed three-component approach to quinolines starting from anilines, aldehydes, and alcohols

A silver-catalyzed sequential formation of two C-C bonds for the construction of a series of polysubstituted quinolines from anilines, aldehydes, and alcohols under mild conditions has been developed. The transformation is effective for a broad range of substrates, including aliphatic alcohols, arylalkanols, cycloalkanols, and ethylene glycol, thereby permitting the expansion of the constituent architectures of the heterocyclic framework.

One-pot synthesis of 2,4-disubstituted quinolines via three-component reaction of amines, aldehydes and alkynes using Al2O3 nanoparticles/methanesulfonic acid (nano-AMA) as a new catalyst

Abstract: An efficient, useful and general procedure for the synthesis of 2,4-disubstituted quinolines via one-pot three-component reaction of aryl amines, aryl aldehydes and phenylacetylene using Al2O3 nanoparticles/methanesulfonic acid (nano-AMA) as a new catalyst has been described. The major advantages of this protocol are high yields, inexpensive catalyst, short reaction times, green and reusable heterogeneous nanocatalyst. It is found that the catalyst is recyclable and can be used up to five times without significant loss of its activity. Graphical Abstract: [Figure not available: see fulltext.]

Iron-Based Imidazolium Salts as Versatile Catalysts for the Synthesis of Quinolines and 2- and 4-Allylanilines by Allylic Substitution of Alcohols

Readily available iron(III)-based imidazolium salts have proven to be very versatile catalysts for the allylic substitution reaction of alcohols with anilines, allowing the synthesis of quinolines, 2-allylanilines and 4-allylanilines just by modulating the reaction conditions. Noteworthy, the formation of quinoline derivatives proceeds by ortho-allylation of the corresponding aniline and subsequent oxidative cyclization mediated by atmospheric oxygen. The reaction using anilines as nucleophiles is selective to the C-alkylation versus the N-alkylation, under any reaction conditions studied. (Figure presented.).

Silver-catalyzed oxidative coupling of aniline and ene carbonyl/acetylenic carbonyl compounds: An efficient route for the synthesis of quinolines

An efficient silver-mediated coupling of aniline with ene carbonyl/acetylenic carbonyl compounds for the synthesis of quinolines is reported. The transformation is effective for a broad range of substrates, thus enabling the expansion of substituent architectures on the heterocyclic framework. The electronic properties of the substituents on the amine have been investigated. It was found that molecules with both electron-donating and electron-withdrawing substituents were suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields. The use of a single catalytic system to mediate chemical transformations in a synthetic operation is important for the development of new atom-economic strategies and this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.

Bronsted acid-mediated reactions of aldehydes with 2-vinylaniline and biphenyl-2-amine

Herein we report simple Bronsted acid-mediated reactions of aldehydes with 2-vinylaniline and biphenyl-2-amine. Ultimately, the useful nitrogen-containing heterocycle derivatives are obtained. The electronic properties of the substituents on the aldehydes and 2-vinylaniline were investigated. It was found that molecules with both electron-donating and -withdrawing substituents were perfectly suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields.

Silver-mediated C-H activation: Oxidative coupling/cyclization of N -arylimines and alkynes for the synthesis of quinolines

A silver-mediated tandem protocol for the synthesis of quinolines involving the oxidative coupling/cyclization of N-arylimines and alkynes has been developed. We demonstrated that scenario-dependent metalation could occur either at the ortho C-H bond of an N-arylimine through protonation-driven enhancement of acidity or at the terminal C-H bond of an alkyne by virtue of the carbophilic π-acidity of silver. The diverse set of mechanistic manifolds implemented with a single type of experimental protocol points toward the importance of stringent reactivity analysis of each individual potentially reactive molecular site. Importantly, the direct arene C-H bond activation provides a unique and distinct mechanistic handle for the expansion of reactivity paradigms for silver. As expected, the protocol allows for the incorporation of both internal and terminal alkynes into the products, and in addition, both electron-withdrawing and -donating groups are tolerated on N-arylimines, thus enabling the vast expansion of substituent architectures on quinoline framework. Further, an intriguing phenomenon of structural isomerization and chemical bond cleavage has been observed for aliphatic internal alkynes.