33471-66-8

Usage

Chemical class

Triazole compounds

Heterocyclic structure

Contains a five-membered ring of two carbon atoms and three nitrogen atoms

Aromatic properties

Due to the presence of benzyl and phenyl groups attached to the triazole ring

Potential applications

Medicinal chemistry, pharmaceuticals, and agrochemicals

Biological activities

Antimicrobial and antitumor effects

Research focus

Drug discovery and development

Additional uses

Ligand in transition metal catalysis and building block in the synthesis of complex organic compounds

InChI:InChI=1/C21H17N3/c1-4-10-17(11-5-1)16-24-21(19-14-8-3-9-15-19)20(22-23-24)18-12-6-2-7-13-18/h1-15H,16H2

Upstream product

• 501-65-5 diphenyl acetylene 
• 622-79-7 benzyl azide 
• 591-50-4 iodobenzene 
• 108717-96-0 1-benzyl-4-phenyl-1H-[1,2,3]triazole 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 105797-59-9 n-butyl phenylacetylenic telluride 
• 536-74-3 phenylacetylene 
• 1432569-33-9 1-benzyl-5-(butyltellanyl)-4-phenyl-1H-1,2,3-triazole 
• 100-39-0 benzyl bromide 
• 932-88-7 1-iodo-2-phenylethyne 
• 108-86-1 bromobenzene 
• 17763-67-6 Phenyl triflate 
• 108-90-7 chlorobenzene 
• 637-44-5 phenylpropyolic acid 

Relevant academic research and scientific papers

Copper-catalyzed: In situ oxidative-coupling for one-pot synthesis of 5-aryl-1,4-disubstituted 1,2,3-triazoles under mild conditions

A new reaction system with CuCl as catalyst, TEA as base and O2/chloramine-T as oxidant was developed for one-pot in situ oxidative-coupling to synthesize 5-aryl-1,4-disubstituted 1,2,3-triazoles in this paper. A variety of 5-arylated-1,2,3-triazole compounds could be efficiently prepared directly from the readily accessible organic azides, terminal alkynes and arylboronic acids. Advantages of the method include use of low-cost catalyst, clean oxidant, less-toxic additive, and low reaction temperature. Importantly, due to avoiding harsh strong basic reagents and high temperatures, the presented method can offer mild conditions for multi-component synthesis of 5-aryl-1,2,3-triazoles from the designed structurally complicated alkynyl or azide donors bearing natural product motifs and sensitive functional groups.

Insight into the Mechanism of the CuAAC Reaction by Capturing the Crucial Au4Cu4-π-Alkyne Intermediate

The classic Fokin mechanism of the CuAAC reaction of terminal alkynes using a variety of Cu(I) catalysts is well-known to include alkyne deprotonation involving a bimetallic σ,π-alkynyl intermediate. In this study, we have designed a CNT-supported atomica

General Synthesis of Tri-Carbo-Substituted N2-Aryl-1,2,3-triazoles via Cu-Catalyzed Annulation of Azirines with Aryldiazonium Salts

The general synthesis of fully substituted N2-aryl-1,2,3-triazoles is hitherto challenging compared with that of the N1-aryl counterparts. Herein, we describe a Cu-catalyzed annulation reaction of azirines and aryldiazonium salts. This regiospecific metho

Copper-Catalyzed Decarboxylative Cycloaddition of Propiolic Acids, Azides, and Arylboronic Acids: Construction of Fully Substituted 1,2,3-Triazoles

A copper-catalyzed decarboxylative cycloaddition of propiolic acids, azides, and arylboronic acids is described. The present reaction provides an efficient and convenient method for the synthesis of various fully substituted 1,2,3-Triazoles from readily available starting materials. A possible mechanism is proposed.

An enolate-mediated regioselective synthesis of 1,2,3-triazoles via azide-aldehydes or ketones [3+2]-cycloaddition reactions in aqueous phase

A synthetic route for the direct conversion of arylazides into the corresponding trizoles via phase transfer catalyst-assisted [3+2] cycloaddition reaction under basic conditions in aqueous medium is reported. This synthetic methodology, which offers high

CuI/Et 2 NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol

A concise one-pot three-component reaction of organic halides, terminal acetylenes, and sodium azide provided an efficient route for the synthesis of 1,2,3-triazoles. A variety of 1,2,3-triazoles were prepared in good to excellent yields with green solven

Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles

Metalated triazoles are the key reactive intermediate of the current click reaction (CuAAC). Bench-stable 5-stannyl triazoles are obtained by a copper-catalyzed interrupted click reaction of easily available terminal alkynes. Subsequent palladium-catalyze

Nickel-Catalyzed Azide-Alkyne Cycloaddition to Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water

Transition-metal-catalyzed or metal-free azide-alkyne cycloadditions are methods to access 1,4- or 1,5-disubstituted 1,2,3-triazoles. Although the copper-catalyzed cycloaddition to access 1,4-disubstituted products has been applied to biomolecular reaction systems, the azide-alkyne cycloaddition to access the complementary 1,5-regioisomers under aqueous and ambient conditions remains a challenge due to limited substrate scope or moisture-/air-sensitive catalysts. Herein, we report a method to access 1,5-disubstituted 1,2,3-triazoles using a Cp2Ni/Xantphos catalytic system. The reaction proceeds both in water and organic solvents at room temperature. This protocol is simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are prepared via this cycloaddition.

A general method of Suzuki-Miyaura cross-coupling of 4- and 5-halo-1,2,3-triazoles in water

A general method of the synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by Suzuki-Miyaura cross-coupling from 4- and 5-halo-1,2,3-triazoles is reported. The reaction is mediated by an expanded-ring N-heterocyclic carbene palladium complex in water. The

Palladium-Catalyzed Regioselective C-5 Arylation of 1,2,3-Triazoles with Diaryliodonium Salts

An effective method for C-5 arylation of 1,4-disubstituted 1,2,3-triazoles and C-5 regioselective arylation of 1-substituted 1,2,3-triazoles via sp 2 C-H activation with palladium as a catalyst and diaryliodonium salts as arylating reagents is described. Various electron-rich and electron-deficient substituents attached to triazoles and diaryliodonium salts were tolerable to give the desired products with good isolated yields in 24 hours under air atmosphere.