73863-52-2

Upstream product

• 73863-47-5 2-chloro-7-methyl-3-phenyl-quinoline 
• 50916-16-0 N-(3-methylphenyl)-2-phenylacetamide 
• 351890-68-1 2-[(3-methylphenyl)amino]-1-phenylethan-1-one 
• 68-12-2 N,N-dimethyl-formamide 
• 1424245-98-6 3-iodo-7-methylquinoline 
• 873-55-2 sodium benzenesulfonate 
• 122-78-1 phenylacetaldehyde 
• 108-44-1 1-amino-3-methylbenzene 
• 96-09-3 styrene oxide 
• 75-75-2 methanesulfonic acid 
• 67-68-5 dimethyl sulfoxide 
• 536-74-3 phenylacetylene 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Method for preparing 3 - arylquinoline

The invention discloses a method for preparing 3 - arylquinoline, which is carried out in an oxygen-containing atmosphere, ortho-amine arylmethanol and aryl formaldehyde in DMSO-solution system containing an alkali to obtain 3 -arylquinoline compounds. In 3 - arylquinoline compound structure prepared by the method, 2 carbon atoms are provided by DMSO, aryl groups at 3 carbon atoms and 3 positions are provided by aryl formaldehyde, and all other atoms in the quinoline compound structure are provided by raw material o-amido aryl methanol. The method for synthesizing 3 - arylquinoline has the advantages of wide raw material sources, environmental friendliness, low price and simple operation, and is beneficial to industrial production.

[3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO

A [3+1+1+1] annulation of arylamines, arylaldehydes, and dimethyl sulfoxide (DMSO) to the pyridine structure in quinolines using DMSO as a nonadjacent dual-methine (═CH?) synthon is disclosed. In this annulation, arylamines provide two carbon atoms and one nitrogen atom, arylaldehydes furnish one carbon atom, and DMSO provides two nonadjacent methines (═CH?) to the pyridine ring in quinoline molecules. This annulation provides a simple approach for the synthesis of 3-arylquinolines from readily available substrates in useful yields. On the basis of the control experiments and the literature, a plausible mechanism is proposed.

Cobalt(III)-Catalyzed, DMSO-Involved, and TFA-Controlled Regioselective C?H Functionalization of Anilines with Alkynes for Specific Assembly of 3-Arylquinolines

Herein, a novel cobalt(III)-catalyzed and TFA-controlled [3+2+1] cyclization of diverse anilines and terminal alkynes has been realized by using DMSO as both the solvent and the C1 source, which led to the specific synthesis of privileged 3-arylquinolines in one pot and regioselectively. Mechanistic investigations revealed that this versatile transformation might be initiated with a C?H activation process and with a 2-vinylbenzenamine species as the active intermediate. (Figure presented.).

Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al2O3/MeSO3H

A highly efficient, simple and environmentally friendly synthesis of 3-arylquinolines has been developed in the presence of Al2O3/ MeSO3H via one-pot reaction of anilines and styrene oxide. This methodology provides very rapid access to 3-arylquinolines in good to excellent yields under solvent-free conditions at room temperature in air.

Metal-free, ionic liquid-mediated synthesis of functionalized quinolines

An expedient and metal-free synthetic protocol for construction of substituted quinolines has been developed from anilines and phenylacetaldehydes using imidazolium cation-based ionic liquids as the reaction medium. Mechanistic analysis indicated that the reaction occurs through C-C and C-N bond formation to produce isolable 2,3-disubstituted quinoline intermediates, which undergo C-C bond cleavage to produce 3-substituted quinolines. The reaction proceeds smoothly with a range of functionalities in good to excellent yields. Advantages of this protocol include metal-free, environmentally friendly, recyclable reaction media, higher yields and shorter reaction times, and thus is promising for the efficient combinatorial synthesis of structurally diverse 2,3-disubstituted and 3-substituted quinolines.

Aerobic synthesis of substituted quinoline from aldehyde and aniline: Copper-catalyzed intermolecular C-H active and C-C formative cyclization

An efficient method for the direct synthesis of substituted quinolines from anilines and aldehydes through C-H functionalization, C-C/C-N bond formation, and C-C bond cleavage has been developed. The method is simple and practical and employs air as an ox

Palladium-catalyzed desulfitative arylation of 3-haloquinolines with arylsulfinates

3-Haloquinolines can be functionalized via a palladium-catalyzed desulfitative coupling of arylsulfinates. This method tolerates substitution upon the aromatic ring and shows good selectivity toward variously substituted aromatic rings. Copyright

Iron-promoted tandem reaction of anilines with styrene oxides via C-C cleavage for the synthesis of quinolines

A novel iron-promoted tandem reaction of anilines with styrene oxides via C-C cleavage and C-H activation has been developed. The reaction utilizes an inexpensive FeCl3 as promoter and is suitable for forming a variety of 3-arylquinolines from

A facile and efficient one-pot synthesis of substituted quinolines from α-arylamino ketones under vilsmeier conditions

An efficient: one-pot synthesis of substituted, quinolines from, α-arylamino ketones in the presence of PBr3 in DMF has been developed. This general protocol provides a novel and facile access to substituted quinolines by sequential Vilsmeier-H

A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 8. Conversion of Anilides into 3-Substituted Quinolines and into Quinoxalines

Anilides (4) (ArNHCOCH2R) are readily converted into 2-chloro-3-R-quinolines (5) under Vilsmeier conditions and the 3-chloro-group may be removed with zinc and acetic acid yielding 3-substituted quinolines (7).When N-nitrosodialkylamines are used in place of dimethylformamide as the Vilsmeier agent, the anilides are converted into 2-chloroquinoxalines in low yields.Several by-products are formed and the mechanisms have been explored.Thus, the formation of ethyl N-arylcarbamate from the corresponding propionanilide is shown to involve an C->O alkyl migration related to a Wolff rearrangement, while N-arylformimidoyl dichloride (18), nitriles, and isocyanides are derived from C-C cleavage of the substituted side-chain.Variation of the acid chloride component of the Vilsmeier reagent or of the solvent was generally unproductive though use of phosphoryl bromide instead of the chloride caused conversion of anilides into bromoquinolines in low yields.