89844-78-0

Upstream product

• 935-02-4 3-Phenyl-2-propynonitrile 
• 622-79-7 benzyl azide 
• 614-16-4 Benzoylacetonitrile 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 591-50-4 iodobenzene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 100-39-0 benzyl bromide 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

Synthesis of fluorine containing N-benzyl-1,2,3-triazoles and N-methyl-pyrazoles from conjugated alkynes

1, 3-Dipolar-cycloaddition reaction of fluoro substituted 3-aryl-propynenitriles 1 with benzyl azide 2 afforded the expected 3-benzyl-5-aryl-3H-[1, 2, 3]triazole-4-carbonitrile 3 and 1-benzyl-5-aryl-1H-[1, 2, 3]-triazole-4-carbonitrile 4 in good yield. Ho

Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition

Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.

Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles

A new method to convert terminal alkynes under relatively mild conditions to 1-cyanoalkynes using in situ formed cyanogen is described. 1-Cyanoalkynes have a higher reactivity than terminal alkynes in the ruthenium(II)-catalyzed regiospecific azide-alkyne cycloaddition to afford 4-cyano-1,2,3-triazoles. A mechanistic proposal different from the one that terminal alkynes adopt under the same reaction conditions is proposed. This work provides a new and convenient two-step sequence to prepare 4-cyano-1,2,3-triazoles from terminal alkynes and organic azides.

A straightforward and versatile approach to the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from alkyl halides via a one-pot, three-component reaction

The preparation of 1,4,5-trisubstituted 1,2,3-triazoles by the coupling of three components (alkyl halides, sodium azide, and active ketones) through an azide-enolate [3+2] cycloaddition (Dimroth cycloaddition) has been developed for the first time. A wide variety of halides (including chlorides, bromides, and iodides as well as primary and secondary derivatives) have demonstrated the versatility of this method, which is based on a one-pot system under mild reaction conditions.

A novel and facile synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from benzylic alcohols through a one-pot, three-component system

A simple one-pot procedure has been developed to efficiently prepare 1,4,5-trisubstituted 1,2,3-triazoles from benzylic alcohols. The presence of diphenylphosphoryl azide (DPPA) and active ketones allows for an azide-enolate [3+2] cycloaddition by use of DBU.

One-pot, three-component synthesis of 1,4,5-trisubstituted 1,2,3-triazoles starting from primary alcohols

A novel, one-pot, three-component approach for the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles through the cycloaddition of a wide range of primary alcohols with sodium azide and active methylene ketones in the presence of N-(p-toluenesulfonyl)imidazole, tetrabutylammonium iodide, and triethylamine in DMF/DMSO has been developed.

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

REACTION OF ACETYLENE NITRILES WITH AZIDES

The addition of organic and inorganic azides to 3-phenylpropynenitrile and 4-phenyl-2-hydroxy-3-butynenitrile was investigated.It was shown that organic azides add to 3-phenylpropynenitrile exclusively at the triple bond.The reaction with aluminum azide takes place with the participation of the acetylene bond and the nitrile group.The reaction of 4-phenyl-2-hydroxy-3-butynenitrile with azides is accompanied by decomposition to phenylpropargylaldehyde with the subsequent formation of 4-formyl-1,2,3-triazole.The oxidation of 4-phenyl-2-hydroxy-3-butynenitrile withactive manganese dioxide with the simultaneous addition of the azides leads to the formation of 4-carboxy-5-phenyl-1,2,3-triazole.