42925-09-7

Upstream product

• 5332-24-1 3-bromoquinoline 
• 5720-05-8 4-methylphenylboronic acid 
• 624-31-7 4-tolyl iodide 
• 181420-00-8 N-[2-(3,3-Diethoxy-prop-1-ynyl)-phenyl]-acetamide 
• 195062-57-8 p-tolylboronic pinacol ester 
• 106-38-7 para-bromotoluene 
• 123726-16-9 bis(4-methylphenyl)iodonium trifluoromethanesulfonate 
• 67-68-5 dimethyl sulfoxide 
• 62-53-3 aniline 
• 766-97-2 4-n-methylphenylacetylene 
• 191162-39-7 quinolin-3-ylboronic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 58784-43-3 4-methylstyrene oxide 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 1202574-26-2 3-(p-tolyl)quinoline 1-oxide 
• 1275591-34-8 8-phenyl-3-p-tolylquinoline 

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.

Lewis acid catalyzed reactivity switch: Pseudo three-component annulation of nitrosoarenes and (epoxy)styrenes

A Lewis acid catalyzed annulation reaction via arene functionalization of nitrosoarenes and C-C cleavage of (epoxy)styrene to provide arylquinolines is reported. The Lewis acid catalyst altered the annulation pattern providing arylquinolines instead of oxazolidines. The reaction with styrene resulted in a mixture of 2,4-diarylquinoline and 4-Arylquinoline, while only 3-Arylquinoline was formed from the reaction of epoxystyrene. This journal is

para-Selective arylation and alkenylation of monosubstituted arenes using thianthreneS-oxide as a transient mediator

Using thianthreneS-oxide (TTSO) as a transient mediator,para-arylation and alkenylation of mono-substituted arenes have been demonstratedviaapara-selective thianthrenation/Pd-catalyzed thio-Suzuki-Miyaura coupling sequence under mild conditions. This reaction features a broad substrate scope, and functional group and heterocycle tolerance. The versatility of this approach was further demonstrated by late-stage functionalization of complex bioactive scaffolds, and direct synthesis of some pharmaceuticals, including Tetriprofen, Ibuprofen, Bifonazole, and LJ570.

Preparation method of para-substituted aryl compound

The invention discloses a preparation method of a para-substituted aryl compound shown as a formula (I) which is described in the specfication. The preparation method is characterized by comprising the following step of: subjecting an aryl sulfonium salt shown as a formula (II) which is described in the specfication and boride to a coupling reaction in a solvent in an inert atmosphere under the action of alkali and a palladium catalyst to obtain the para-substituted aryl compound. According to the method, mono-substituted aromatic hydrocarbon is taken as a substrate, the aryl sulfonium salt isconstructed in situ, and the palladium catalyst catalyzes the aryl sulfonium salt constructed in situ to undergo the Suzuki-Miyaura coupling reaction, so a mono-substituted aromatic hydrocarbon para-arylation or alkenylation product is constructed quickly and efficiently. The method is mild in conditions, high in substrate universality and wide in tolerance of a heterocyclic coupling substrate.

Rh-Catalyzed C-H Amination/Annulation of Acrylic Acids and Anthranils by Using -COOH as a Deciduous Directing Group: An Access to Diverse Quinolines

A method for the synthesis of diverse polysubstituted quinolines from readily available acrylic acids and anthranils has been developed. The weakly coordinating -COOH directing group, which can be tracelessly removed in the cascade cyclization, is essential for this reaction. Diverse polysubstituted quinolines were obtained under mild reaction conditions with simple H2O and CO2 as byproducts. More importantly, 1,2,3,4-tetrahydroacridine, which is the core skeleton of tacrine (an Alzheimer's disease drug), was conveniently synthesized.

Copper-Catalyzed Ring-Opening/Reconstruction of Anthranils with Oxo-Compounds: Synthesis of Quinoline Derivatives

A copper-catalyzed protocol for the construction of various 2-aryl(alkyl)-3-acylquinolines or 3-arylquinolines using readily available anthranils and 1,3-diketones or aldehydes as starting materials is reported herein. Dioxygen as the sole oxidant and hexafluoroisopropanol as the solvent play an important role in both procedures. This ring-opening/reconstruction strategy involving N-O bond cleavage and C-N/C-C bond formation features high yields and broad substrate scope.

Method for synthesizing quinoline derivatives

The invention discloses a method for synthesizing quinoline derivatives. 2,1-benzisoxazole derivatives represented by formula I and phenylacetaldehyde derivatives represented by formula II are used as raw materials, and are reacted to obtain the quinoline

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.).

Spectral properties and photoreactivity of sydnonyl-stilbenes

This work follows an earlier one where some sydnone derivatives, interesting for their biological and biomedical applications, were synthesized and the effect of substituents on their photoreactivity was studied in irradiation conditions of high intensity and high substrate concentrations. The aim of the present work is to investigate the deactivation pathways of the excited states of three of these compounds, bearing a stilbene moiety, and to determine the quantum yield of the competitive fluorescence/photoreactions in soft irradiation conditions. Flash photolysis measurements with nanosecond resolution were also carried out to obtain information on the transient intermediates responsible for the photoproducts found in the previous work. The oxygen effect on the photoproducts and the energy transfer from triplet donors were also investigated. The experimental results, supported by quantum chemical calculations, showed that different substituents at the sydnone ring can drive the photoreactivity towards different products, thus confirming the results of the previous work. In particular, phenyl-substitution favours the formation of benzodiazepine derivatives.