17282-99-4

Upstream product

• 60-12-8 2-phenylethanol 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 13209-38-6 (2-aminophenyl)(phenyl)methanol 
• 42599-24-6 E-styryl iodide 
• 100-42-5 styrene 
• 501-65-5 diphenyl acetylene 
• 103-70-8 Formanilid 
• 100-52-7 benzaldehyde 
• 67-68-5 dimethyl sulfoxide 
• 1203703-02-9 4-methyl-N-phenyl-N-(3-phenylprop-2-yn-1-yl)benzenesulfonamide 
• 305837-95-0 4-methyl-N-(3-phenylprop-2-yn-1-yl)benzenesulfonamide 
• 66003-76-7 Diphenyliodonium triflate 
• 98-80-6 phenylboronic acid 
• 809274-63-3 3-iodo-4-phenylquinoline 

Downstream Products

• 37118-71-1 3,4-diphenyl-2-(1H)-quinolinone 

Relevant academic research and scientific papers

Flash Vacuum Thermolysis of 5-Substituted-4,4-diphenyl-3-oxa-1-azabicyclohexan-2-ones. A New Route to Quinolines.

Thermolysis of bicyclic carbamates produces quinoline derivatives in good yields.A two step reaction is described. Key Words: Flash vacuum thermolysis; 5-substituted-4,4-diphenyl-3-oxa-1-azabicyclohexan-2-ones; quinolines.

Unexpected Annulation between 2-Aminobenzyl Alcohols and Benzaldehydes in the Presence of DMSO: Regioselective Synthesis of Substituted Quinolines

An unexpected annulation among 2-aminobenzyl alcohols, benzaldehydes, and DMSO to quinolines has been disclosed. For the reported annulation between 2-aminobenzyl alcohols and benzaldehydes, the change of the solvent from toluene to DMSO led to the change of the product from the diheteroatomic cyclic benzoxazines to monoheteroatomic cyclic quinolines. This annulation can be used to synthesize regioselectively different substituted quinolines by the choice of different 2-amino alcohols, aldehydes, and sulfoxides as substrates. Interestingly, introducing substituent groups to the α-position of sulfoxides resulted in the interchange of the positions between benzaldehydes and sulfoxides in the product quinolines. On the basis of the control experiments and literatures, a plausible mechanism for this annulation was proposed.

Method for preparing 3,4-disubstituted quinoline from 1-o-aminophenyl alcohol and aromatic aldehyde

The invention discloses a method for preparing 3,4-disubstituted quinoline from 1-ortho-aminophenyl alcohol and aromatic aldehyde, which comprises the following steps: in an oxygen-containing atmosphere, carrying out one-pot reaction on 1-ortho-aminophenyl alcohol and aryl formaldehyde in an alkali-containing DMSO (Dimethylsulfoxide) solution system to obtain a 3,4-disubstituted quinoline compound. In the structure of the 3,4-disubstituted quinoline compound prepared by the method, a 2-position carbon atom is provided by DMSO, a 3-position carbon atom and an aryl group on the 3-position are provided by aryl formaldehyde, and all other atoms in the quinoline compound structure and a substituent group on a 4-position carbon atom are provided by 1-o-aminophenyl alcohol. The method for synthesizing the 3,4-disubstituted quinoline is wide in raw material source, easy to obtain, green, environment-friendly, low in price, simple to operate and beneficial to industrial production.

Preparation of 3-Iodoquinolines from N-Tosyl-2-propynylamines with Diaryliodonium Triflate and N-Iodosuccinimide

4-Aryl and 4-alkyl substituted 3-iodoquinolines could be smoothly obtained in one pot by treating N-tosyl-2-propynylamines with diaryliodonium triflate in the presence of K3PO4 and a catalytic amount of CuCl at room temperature, followed by treatment with N-iodosuccinimide and BF3·OEt2 at 0 °C, and then NaOH in methanol solution. The product, 3-iodo-4-phenylquinoline was smoothly transformed into 4-phenylquinoline with zinc; 4-phenyl-3-toluenesulfenylquinoline with toluenethiol, K2CO3, and CuI; 4-phenyl-3-phenylethynylquinoline with the Sonogashira coupling reaction; 4-phenyl-3-styrylquinoline with the Heck coupling reaction; 3,4-diphenylquinoline with the Suzuki-Miyaura coupling reaction; 2-cyclohexyl-3-iodo-4-phenylquinoline with cyclohexanecarboxylic acid, Ag2CO3, and K2S2O8; and 3-iodo-2-(2′,5′-dioxan-1′-yl)-4-phenylquinoline with benzoyl peroxide in dioxane.

Control over Organometallic Intermediate Enables Cp?Co(III) Catalyzed Switchable Cyclization to Quinolines and Indoles

Achieving controllable C-H functionalization to elaborate valuable compounds from simple chemicals is attractive and highly desirable, especially if nonprecious transition metal catalysts can be used. However, controlling selectivity in these transformations remains a continuous challenge to synthetic chemists. Herein, we show for the first time that control over the reactive organometallic intermediate enables the switchable synthesis of quinoline and indole from amides and alkynes through C-H activation using Cp?Co(III). The keys to this strategy are (1) introducing a Lewis acid to greatly accelerate the dehydrative cyclization, which can outcompete dehydrogenative cyclization, and (2) tuning the directing group to facilitate the dehydrogenative cyclization and inhibit dehydrative cyclization.

Copper-catalyzed synthesis of substituted quinolines via C-N coupling/condensation from ortho -acylanilines and alkenyl iodides

An efficient cascade copper-catalyzed intermolecular Ullmann-type C-N coupling/enamine condensation reaction is described, in which ortho-acylanilines and alkenyl iodides converted to multisubstituted quinolines in good to excellent yields.

Copper promoted synthesis of substituted quinolines from benzylic azides and alkynes

A novel copper promoted synthesis of substituted quinolines from various benzylic azides and internal alkynes has been demonstrated. The reaction features a broad substrate scope, high product yields and excellent regioselectivity. In contrast to the known two-step process of acid promoted [4 + 2] cycloaddition reaction and oxidation, the present methodology allows the synthesis of quinolines in a single step under neutral reaction conditions and can be applied to the synthesis of biologically active 6-chloro-2,3-dimethyl-4-phenylquinoline (antiparasitic agent) and 3,4-diphenylquinolin-2(1H)-one (p38αMAP kinase inhibitor). A plausible reaction mechanism involves rearrangement of benzylic azide to N-arylimine (Schmidt reaction) followed by intermolecular [4 + 2] cycloaddition with internal alkynes.

Palladium(ii)-catalysed regioselective synthesis of 3,4-disubstituted quinolines and 2,3,5-trisubstituted pyrroles from alkenes via anti-Markovnikov selectivity

A novel strategy has been identified for the regioselective synthesis of 3,4-disubstituted quinolines and 2,3,5-trisubstituted pyrroles from simple alkenes via anti-Markovnikov selectivity under palladium catalysis. The salient features are synthesis of two different heterocycles, readily available starting materials, broad substrate scope, moderate to good yields and use of molecular oxygen as a terminal oxidant.

Transition-metal-free indirect Friedl?nder synthesis of quinolines from alcohols

(Chemical Equation Presented) The synthesis of polysubstituted quinolines can be easily and greenly accomplished by the direct reaction between the corresponding 2-aminobenzylic alcohol derivative and either a ketone or alcohol in the presence of a base, without any transition-metal catalyst.

RuCl2(dmso)4 catalyzes the solvent-free indirect Friedlaender synthesis of polysubstituted quinolines from alcohols

The first synthesis of polysubstituted quinoline derivatives from aromatic or aliphatic alcohols with RuCl2(dmso)4 as catalyst under solvent-free conditions is described. The reaction involves the in situ oxidation of alcohols to the