4874-87-7

Upstream product

• 1807-69-8 2-diazo-3-oxo-3-phenyl-propionic acid methyl ester 
• 62-53-3 aniline 
• 53431-72-4 α-nitro cinnamate de methyle 
• 622-37-7 Phenyl azide 
• 79-22-1 methyl chloroformate 
• 536-74-3 phenylacetylene 
• 103-26-4 methyl cinnamate 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 108-86-1 bromobenzene 
• 110996-38-8 2-hydroxyimino-3-oxo-3-phenyl-propionic acid methyl ester 

Downstream Products

• 138043-75-1 methyl 3-phenyl-1H-indole-2-carboxylate 

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

Photochemical C–H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D

The photolysis of N-aryltriazoles and N-arylbenzotriazoles leads to indoles and carbazoles, respectively. Because libraries of triazoles can be accessed rapidly, for example by the copper-catalyzed [3+2] cycloaddition reaction between alkynes and azides, this reaction allows the preparation of indoles in a single operation, by the simultaneous photolysis of the precursor library. As an example of such a synthesis of carbazoles, we prepared for the first time clausenawalline D, an antimalarial alkaloid that was recently isolated.

Cycloadduct formation of α,β-unsaturated esters with azides catalyzed by NHC systems

NHC-catalyzed cycloadduct formation of α,β-unsaturated esters with azides has been developed. This strategy could generate 1,2,3-triazoles and dihydropyrazoles with high yields and regioselectivities in the presence of an N-heterocyclic carbene catalyst.

Copper Acetate Catalyzed Regio-selective Synthesis of Substituted 1,2,3-Triazoles: A Versatile Azide–Alk-ene Cycloaddition/Oxidation Approach

A copper acetate catalyzed oxidative cycloaddition reaction of benzyl and aryl azides with terminal and internal olefins that contain electron-withdrawing groups (COOR, CONH2, CN, CHO, COR) has been developed. The reaction employs air as the oxidant and does not require any base or additives to afford 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles in good to excellent yields with high regioselectivity.

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.

Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited

After revisiting earlier works reporting the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles via the addition of bromomagnesium acetylides to azides, much improved yields of the products were obtained for a wide array of azides and alkynes. The intermediates of that reaction can be trapped with different electrophiles to regioselectively form 1,4,5-trisubstituted 1,2,3-triazoles.

REACTIONS DES METHYLAZIDE ET PHENYLAZIDE AVEC QUELQUES ALCYNES ET OLEFINES α-NITREES. SYNTHESE REGIOSPECIFIQUE DES 1,2,3 TRIAZOLES

The reactions of alkynes and α-nitro-olefines with methylazide and phenylazide was studied.In contrast to known reactions with alkynes which are non-regioselective, methylazide and phenylazide react regiospecifically with α-nitro-olefines and give only one type of triazole after elimination of HNO2.These reactions are very useful synthetic approaches to 1,2,3 triazoles.