104967-52-4

Upstream product

• 619-42-1 4-methoxycarbonylphenyl bromide 
• 221910-00-5 3-(2-aminophenyl)-1-(4-methoxycarbonylphenyl)prop-2-yn-1-one 
• 74-88-4 methyl iodide 
• 91-22-5 quinoline 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 59-31-4 2-hydroxyquinoline 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 3609-53-8 methyl 4-acetylbenzoate 
• 552-89-6 2-nitro-benzaldehyde 
• 2637-37-8 Quinoline-2-thiol 
• 2005-43-8 2-bromoquinoline 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 1354658-33-5 C₂₄H₁₇ClN₂O₅ 

Relevant academic research and scientific papers

Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions

Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0-catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi-step transformations. Here we introduce base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones. We show that under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.

Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst

A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding β-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the Cα-Cβ single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.

On-Water Synthesis of 2-Substituted Quinolines from 2-Aminochalcones Using Benzylamine as the Nucleophilic Catalyst

On-water synthesis of 2-substituted quinolines from 2-aminochalcone derivatives was developed using benzylamine as the nucleophilic catalyst. Various 2-aminochalcones could be applied to this protocol, and the desired 2-substituted quinoline products were isolated in excellent yields by simple filtration. Furthermore, we elucidated the role of benzylamine in this transformation and provided the detailed reaction mechanism. This protocol has several additional advantages, such as simple operation, broad substrate scope, good functional group tolerance, easy product isolation, recycling of the catalyst, and gram-scale synthesis.

Quinoline derivative synthesis method

The invention discloses a quinoline derivative synthesis method. The method comprises the steps that substitutional acetophenone, aniline and dimethyl sulfoxide perform one-pot reaction in an oxygen-containing atmosphere in the presence of a copper salt catalyst to obtain a quinoline derivative. The quinoline derivative types are enriched and more intermediates are provided for drug synthesis by adopting the method, raw materials are wide in source, the steps are simple, reaction conditions are mild, the yield is high, and the method facilitates industrial production.

Method for intermolecular cyclization synthesis of quinoline derivative

The invention discloses a method for intermolecular cyclization synthesis of a quinoline derivative. The method comprises the following step: in an atmosphere of oxygen, performing a one-pot reactionon aryl aceton, phenylamine and dimethyl sulfoxide in the presence of a ferric salt and/or ferrite catalyst, thereby obtaining the quinoline derivative. By adopting the method, the types of quinolinederivatives are enriched, a relatively large amount of intermittent are provided for medicine synthesis, and in addition, the method is wide in raw material source, simple in step, gentle in reactioncondition, high in yield and beneficial to industrial production.

Functional Mechanically Interlocked Molecules: Asymmetric Organocatalysis with a Catenated Bifunctional Br?nsted Acid

Interlocked molecules, such as catenanes, rotaxanes, and molecular knots, have become interesting candidates for the development of sophisticated chemical catalysts. Herein, we report the first application of a catenane-based catalyst in asymmetric organo

Convergent synthesis of 2-aryl-substituted quinolines by gold-catalyzed cascade reaction

Gold-catalyzed auto-tandem catalysis has been developed for synthesizing 2-aryl-substituted quinolines. The reaction of an aniline bearing an acetal moiety with an aryl alkyne proceeded via formal [4+2]-cycloaddition, which involved the addition of gold acetylide to an oxonium ion to give amino alkyne intermediate and sequential 6-endo-dig cyclization of amino alkyne intermediate by attacking of nitrogen to alkyne moiety activated by gold catalyst. The cationic gold catalyst promoted two different processes by enhancing the nucleophilicity and electrophilicity of alkyne. This convergent synthetic methodology enabled the synthesis of a variety of 2-aryl-substituted quinolines.

PdCl2(dppf)-catalyzed in situ coupling of 2-hydroxypyridines with aryl boronic acids mediated by PyBroP and the one-pot chemo- and regioselective construction of two distinct aryl-aryl bonds

We present a PdCl2(dppf)-catalyzed synthesis of 2-arylated pyridine derivatives via the in situ coupling of 2-OH pyridines and boronic acids mediated by PyBroP. In addition, the highly chemo- and regioselective construction of two different aryl-aryl bonds via a one-pot operation has also been demonstrated by the orthogonal use of this method with the Ni-catalyzed Suzuki-Miyaura coupling of phenols.

Nickel-catalyzed reaction of arylzinc reagents with N-aromatic heterocycles: A straightforward approach to C-H bond arylation of electron-deficient heteroaromatic compounds

(Chemical Equation Presented) The reaction of electron-deficient N-heteroaromatic compounds, such as pyridines and quinolines, with arylzinc reagents in the presence of a catalytic amount of a nickel complex affords the arylated products. The reaction is likely to proceed through a formal nucleophilic 1,2-addition, thus exhibiting a reactivity complementary to conventional direct arylation through electrophilic substitution.

The palladium-catalyzed transfer hydrogenation/heterocyclization of β- (2-aminophenyl)-α,β-ynones. An approach to 2-aryl- and 2-vinylquinolines

The palladium-catalyzed transfer hydrogenation/cyclization of readily available β-(o-aminophenyl)-α,β-ynones I affords 2-aryl- and 2- vinylquinolines 3 in good yield.