87797-63-5

Upstream product

• 5877-59-8 (E)-3-methoxy-N-(phenylmethylene)benzenamine 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 536-74-3 phenylacetylene 
• 1520098-57-0 methyl phenylacetylenedicarboxylate 
• 536-90-3 m-Anisidine 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 13031-49-7 N-(3-methoxyphenyl)benzamide 
• 103-64-0 bromostyrene 
• 60-12-8 2-phenylethanol 
• 100-52-7 benzaldehyde 
• 16717-64-9 1-azidostyrene 
• 5877-59-8 N-benzylidene-m-anisidine 
• 4098-17-3 1-(1-azido-2-iodoethyl)benzene 
• 100-42-5 styrene 

Relevant academic research and scientific papers

One-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed three-component cascade annulation of amines, alkyne esters and terminal alkynes

Described herein is a new and general method for one-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed [3 + 1 + 2] annulation of simple amines, alkyne esters and terminal alkynes. The versatile transformation might initiate with the facil

Metal-free synthesis of quinolines by direct condensation of amides with alkynes: revelation of N-aryl nitrilium intermediates by 2D NMR techniques

Employing triflic anhydride/2-fluoropyridine as an activation system, the coupling reactions of secondary N-aryl amides with terminal alkynes yielded substituted quinolines in moderate to excellent yields. The reaction tolerated both electron-donating and electron-withdrawing groups at the benzamide moiety. Electron-rich aryl acetylenes served as excellent coupling partners, and aliphatic terminal alkynes such as cyclopropyl and conjugate vinyl acetylenes could also be used as reaction partners. By means of 2D NMR techniques (heteronuclear multiple bond correlation (HMBC), heteronuclear single quantum correlation (HSQC)), nitrilium ions were probed as reactive intermediates which are in contrast with that suggested by Movassaghi on the basis of in situ IR monitoring experiments. On the basis of these results, a plausible mechanism for the formation of quinolines was suggested.

A medicine intermediate quinoline synthetic method of the compound

The invention provides a synthetic method of a quinoline compound as shown in the following formula (III). The method comprises the following steps: in an organic solvent, in existence of a catalyst, an accelerant and alkali, enabling a compound as shown in the formula (I) and a compound as shown in the formula (II) to carry out a reaction, so as to obtain a compound as shown in the formula (III), wherein R is H, C1-C6 alkyl, C1-C6 alkoxy or halogen. According to the method, the plurality of factors such as the catalyst, the accelerant, alkali and the organic solvent are selected, and the target product can be obtained at a high yield, so that the synthetic method can achieve a good industrial application value in the technical field of medical intermediate synthesis.

Method for synthesizing quinoline derivative

The invention provides a method for synthesizing a quinoline derivative. Aromatic amine, electrophilic alkyne and alkyne are sequentially added into a reaction vessel according to the molar ratio of 1:1:(1.2-4), solvent is added according to the proportion that 2-4 mL of solvent is added into 1 mmol of aromatic amine, then catalyst silver trifluoromethanesulfonate (AgOTf) with the molar weight being 0.8-5% that of aromatic amine and additive trifluoromethanesulfonic acid (HOTf) with the molar weight being 1.8-10% that of aromatic amine are added, reaction is conducted for 8-24 h at 100-120 DEG C in oil bath, the product is cooled to room temperature, water is added, the product is extracted three times with ethyl acetate, organic layers are combined, decompressive condensing is conducted, the product is subjected to column chromatography purification, and the product, namely the quinoline derivative, is obtained. The quinoline derivative has the advantages that reaction substrates are low in price, the yield is high, selectivity is good, separation and purification are easy, pollution is little, and steps are simple.

A method for the synthesis of quinoline derivatives

The invention belongs to the technical field of organic synthesis and particularly relates to a synthesis method of quinoline derivatives. The synthesis method comprises the steps of sequentially adding aromatic amine, aldehyde and alcohol into a reaction

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.

Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines

Highly functionalized quinolines and pyridines could be synthesized by BF3?OEt2-mediated reactions of vinyl azides with N-aryl and N-alkenyl aldimines, respectively. The reaction mechanism could be characterized as formal [4+2]-annulation, including unprecedented enamine-type nucleophilic attack of vinyl azides to aldimines and subsequent nucleophilic cyclization onto the resulting iminodiazonium ion moieties.

Annulation Reactions with Iron(III) Chloride: Oxidation of Imines

Aromatic imines react with phenylacetylene or styrene in an acetonitrile solution of iron(III) chloride to give quinolines 3 or their tetrahydro derivatives 11 together with variable amounts of products 4 arising from the reduction of the imines.The initial step appears to be a one-electron oxidation to generate iron(II) and an imine radical cation.When the reactions are carried out in the presence of stoichiometric amounts of tetrachloro-p-benzoquinone (chloranil), only quinolines 3 are obtained.

THE REACTION OF IMIDOYL RADICALS WITH MULTIPLE CARBON-CARBON BONDS

A general view on the reaction between imidoyl radicals and carbon-carbon double or triple bonds is given; the synthesis of substituted quinolines starting from imines and alkenes is described, pointing out the differences with respect to the analogous reaction performed with alkynes.