14758-20-4

Upstream product

• 854628-01-6 1-phenyl-1H-[1,2,3]triazole-4,5-dicarbonyl chloride 
• 71-43-2 benzene 
• 98-86-2 acetophenone 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 622-37-7 Phenyl azide 
• 62-53-3 aniline 
• 1215-50-5 1-phenyl-3-(phenylamino)prop-2-en-1-one 
• 93-54-9 1-Phenyl-1-propanol 
• 29954-08-3 (Z)-1,4-diphenyl-2-(phenylamino)but-2-ene-1,4-dione 
• 127-19-5 N,N-dimethyl acetamide 
• 68-12-2 N,N-dimethyl-formamide 
• 503595-76-4 3-(tri(isopropyl)silyl)-1-phenylprop-2-yn-1-one 
• 98-88-4 benzoyl chloride 
• 18212-29-8 5-phenyl-1,2,3-thiadiazole 

Downstream Products

• 22758-02-7 1-phenyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid 
• 4600-04-8 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid 
• 15966-72-0 1-phenyl-1H-1,2,3-triazole-5-carboxylic acid 

Relevant academic research and scientific papers

Terminal Acetylenic Iminium Salts: Cycloaddition Reactions with Azides Leading to 1,2,3-Triazoles and Bicyclic 1,2,3-Triazolium Salts

Terminal acetylenic iminium triflate salts [HC≡C-C(R)=N+Me2 TfO–] represent very potent dipolarophiles which undergo [3+2] cycloadditions with aryl and benzyl azides at very mild and uncatalyzed conditions, yielding 1,4-disubstituted 1,2,3-triazoles with complete regioselectivity. Addition of nucleophiles at the iminium group of the cycloadducts leads to diverse 1-aryl-(or benzyl-)-4-dimethylaminomethyl-1,2,3-triazoles. The first formed cycloaddition adducts subsequently react with a second molecule of the acetylenic iminium salt by a consecutive Michael addition/1,5-cyclization to form 2,4-dihydropyrrolo[1,2-c][1,2,3]triazol-7-ium triflates. Further transformations of the latter salts are described, among them the conversion into a mesoionic carbene, isolated as a monomeric silver(I) complex.

Copper-catalyzed multiple oxidation and cycloaddition of aryl-alkyl ketones (alcohols) for the synthesis of 4-acyl- and 4-diketo-1,2,3-triazoles

A Cu/TEMPO-catalyzed tandem multiple oxidative dehydrogenation and cycloaddition has been developed, which affords 4-acyl-1,2,3-triazoles and 4-diketo-1,2,3-triazoles from readily-available aryl-alkyl ketones (or alcohols) and different organic azides. Moreover, the reaction used environmentally friendly dimethyl carbonate (DMC) as the solvent and air as the oxidant, and H2O was the only by-product, so it provides a green and practical synthetic method for 1,2,3-triazoles.

Regitz Diazo Transfer Reaction for the Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles and Subsequent Regiospecific Construction of 1,4-Disubstituted 1,2,3-Triazoles via C-C Bond Cleavage

A straightforward and efficient methodology has been developed for the synthesis of 1,4,5-trisubstituted dicarbonyl 1,2,3-triazoles and 1,4-disubstituted sole-carbonyl 1,2,3-triazoles via a C-C bond cleavage process. The Regitz diazo transfer and C-C bond cleavage were the key steps of this transformation, which provided diverse carbonyl-substituted structural 1,2,3-triazoles. This reaction featured with excellent regioselectivity, wide functional group tolerance, and mild conditions.

Method for synthesizing 4-acetyl-1,2,3-triazole compound through solvent participating in reaction

The invention relates to a method for synthesizing a 4-acetyl-1,2,3-triazole compound through a solvent participating in a reaction. The solvent participating in the reaction provides a carbon source, the solvent is one of DMA, DMSO, TMEDA and DMF-DMA, metal salt is used as a catalyst, the TMEDA is used as a ligand and an oxidant, and a methyl ketone compound and organic azide undergo a one-pot reaction. The cheap and easily available solvent participates in the reaction, the copper salt is used as the catalyst, and the methyl ketone compound and the organic azide undergo the one-pot reaction, so the method has the characteristics of mild reaction conditions, high yield, easily available raw materials, and convenience in effective synthesis of the 4-acetyl-1,2,3-triazole compound; and compared with existing methods, the method disclosed in the invention has the advantages of mild reaction conditions, short reaction time, good safety, simplicity in operation, wide substrate application, high reaction efficiency and cheap catalyst, and is a method having potential application values.

Copper-Catalyzed Oxidative Cross-Dehydrogenative Coupling/Oxidative Cycloaddition: Synthesis of 4-Acyl-1,2,3-Triazoles

A copper-catalyzed three-component reaction of methyl ketones, organic azides, and various one-carbon (C1) donors was developed that provides 4-acyl-1,2,3-triazoles in moderate to good yields. While DMF, DMA, TMEDA, or DMSO can serve as the C1 donor, best yields were obtained using DMF. The transformation is proposed to proceed via an oxidative C-H/C-H cross-dehydrogenative coupling followed by an oxidative 1,3-dipolar cycloaddition.

Base-Promoted Synthesis of N-Substituted 1,2,3-Triazoles via Enaminone-Azide Cycloaddition Involving Regitz Diazo Transfer

The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azi

Metal-Free Route for the Synthesis of 4-Acyl-1,2,3-Triazoles from Readily Available Building Blocks

Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.

An efficient and high-yielding one-pot synthesis of 4-acyl-1,2,3-triazoles via triisopropylsilyl-protected ynones

A practical and efficient process has been developed for the synthesis of 1-substituted 4-acyl-1H-1,2,3-triazoles using a three-step one-pot synthetic approach. This transformation involves an initial preparation of triisopropylsilyl (TIPS)-protected ynon

Thermal Rearrangement of 4-Iminomethyl-1,2,3-thiadiazoles

Imines derived from 1,2,3-thiadiazole-4-carbaldehyde 4 rearrange thermally into 1,2,3-triazole-4-thiocarbaldehydes 6 which were trapped with anthracene or 2,3-dimethylbutadiene.In two cases, 1,2,3-thiadiazole-4-thiocarbaldehyde 9 was intercepted as the Di