52187-83-4

Upstream product

• 2216-94-6 phenylpropynoic acid ethyl ester 
• 622-37-7 Phenyl azide 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 62-53-3 aniline 
• 626-35-7 nitroacetic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 103-36-6 ethyl 3-phenyl-2-propenoate 

Relevant academic research and scientific papers

A simple route towards the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from primary amines and 1,3-dicarbonyl compounds under metal-free conditions

An acetic acid-promoted approach that enables the synthesis of 1,4,5-trisubstituted 1,2,3-triazole derivatives has been achieved. This transformation employs readily available primary amines, 1,3-dicarbonyls and tosyl azide as the starting materials via a

Nucleophilic Iron Complexes in Proton-Transfer Catalysis: An Iron-Catalyzed Dimroth Cyclocondensation

The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) is an active catalyst in C?H-amination but also in proton-transfer catalysis. Herein, we describe the successful use of this complex as a proton-transfer catalyst in the cyclocondensation reaction between azides and ketones to the corresponding 1,2,3-triazoles. Cross-experiments indicate that the proton-transfer catalysis is significantly faster than the nitrene-transfer catalysis, which would lead to the C?H amination product. An example of a successful sequential Dimroth triazole–indoline synthesis to the corresponding triazole-substituted indolines is presented.

A metal-free three-component reaction for the regioselective synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

A metal-free three-component reaction to synthesize 1,4,5-trisubstituted 1,2,3-triazoles from readily available building blocks,such as aldehydes,nitroalkanes,and organic azides,is described. The process is enabled by an organocatalyzed Knoevenagel condensation of the formyl group with the nitro compound,which is followed by the 1,3-dipolar cycloaddition of the azide to the activated alkene. The reaction features an excellent substrate scope,and the products are obtained with high yield and regioselectivity. This method can be utilized for the synthesis of fused triazole heterocycles and materials with several triazole moieties.

Lewis base catalyzed aerobic oxidative intermolecular azide-zwitterion cycloaddition

The discovery of a novel aerobic oxidative intermolecular azide-zwitterion reaction catalyzed by an organocatalyst is presented. It is demonstrated that the merger of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene and electrondeficient olefins generates reactive zwitterion intermediates, which readily participate in cycloaddition reactions with an array of azides, thus providing facile entry to fully or highly substituted 1,2,3-triazole frameworks. The reaction features an excellent substrate scope, and the products are obtained with high yields and excellent regioselectivities. It is demonstrated that some of these products can be transformed into pharmaceutically important agents. In addition to the experimental results, a detailed mechanistic survey is also provided, including MS studies rationalizing the origin of regioselective control.

Organocatalytic 1,3-dipolar cycloaddition reactions of ketones and azides with water as a solvent

We reported an enamine catalyzed strategy to fully promote a 1,3-dipolar cycloaddition to access a vast pool of substituted 1,2,3-triazoles with water as the only solvent.

Amine-catalyzed [3+2] Huisgen cycloaddition strategy for the efficient assembly of highly substituted 1,2,3-triazoles

An enamine-catalyzed strategy has been utilized to fully promote the Huisgen [3+2] cycloaddition with a broad spectrum of carbonyl compounds and azides, thereby permitting the efficient assembly of a vast pool of highly substituted 1,2,3-triazoles. In par

Organocatalytic enamide-azide cycloaddition reactions: Regiospecific synthesis of 1,4,5-trisubstituted-1,2,3-triazoles

Heterocycles in one click: A novel organocatalytic enamide-azide cycloaddition reaction has been developed. This synthetic procedure represents a new method for the efficient construction of 1,4,5-trisubstituted-1,2,3- triazoles under mild reaction condit