31794-11-3

Usage

Chemical Class

Triazole compounds

Usage

Building block for the synthesis of pharmaceuticals, agrochemicals, and materials

Biological Activities

Antimicrobial, antifungal, and anticancer properties

Safety Precautions

Handle with caution and follow proper safety protocols due to potential hazards and risks associated with its use.

Upstream product

• 70978-37-9 1-(azidomethyl)-4-methoxybenzene 
• 126623-60-7 ethyl <3-oxo-2H-isothiazol-2-yl>acetate 1,1-dioxide 
• 288-36-8 1,2,3-triazole 
• 677-25-8 ethylenesulfonyl fluoride 
• 74-86-2 acetylene 
• 75-20-7 calcium carbide 
• 824-94-2 p-methoxybenzyl chloride 
• 1066-54-2 trimethylsilylacetylene 
• 108-05-4 vinyl acetate 
• 180723-17-5 1-(4-Methoxybenzyl)-1H-1,2,3-triazole-4,5-dicarboxylic acid 

Downstream Products

• 180791-68-8 3-p-methoxybenzyl-1,2,3-triazole-1-oxide 
• 288-36-8 1,2,3-triazole 
• 1421036-30-7 1-(4-methoxy-3,5-dinitrobenzyl)-1H-1,2,3-triazole 
• 1620125-37-2 2-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-5-yl)pyridine 1-oxide 
• 1620125-40-7 2-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-5-yl)-4-methylpyridine 1-oxide 
• 1620125-39-4 2-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-5-yl)-5-methylpyridine 1-oxide 
• 805315-84-8 1-(3-bromo-4-methoxybenzyl)-4-bromo-1,2,3-triazole 

Relevant academic research and scientific papers

Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides

The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI-catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts.

Self-Assembled Polymeric Pyridine Copper Catalysts for Huisgen Cycloaddition with Alkynes and Acetylene Gas: Application in Synthesis of Tazobactam

Novel convoluted polymeric pyridine copper(I) catalysts PVPy-Cu were developed for the Huisgen cyclization of organic azides using alkynes and acetylene gas. They were readily prepared based on our molecular convolution of CuSO4·5H2O and poly(4-vinylpyridine) (PVPy) in the presence of sodium ascorbate with and without various sodium salts in water. Their structural investigation was conducted using XANES and EXAFS, as well as DFT calculation. The Huisgen cycloaddition of a variety of alkynes and acetylene gas was carried out using 100 to 800 mol ppm of Cu of PVPy-Cu in water, whose turnover numbers reached up to 10 000. This catalytic system was applied to the synthesis of tazobactam, which is an inhibitor of bacterial β-lactamases.

1 H - 1, 2, 3 - triazole preparation method (by machine translation)

The invention belongs to the field of fine chemical pharmaceutical intermediates, discloses a 1 H - 1, 2, 3 - triazole of the preparation method. The method to replace the halogen animal pen and sodium azide in fat alcohol and water in the mixed solvent of azide, after being extracted by the organic solvent, directly with the acetylene in a pressure reactor in the reaction process for preparing the intermediate, then separating out intermediate, obtained through the strong acid debenzylation 1 H - 1, 2, 3 - triazole, through the rectification is purified to high purity of 1 H - 1, 2, 3 - triazole finished product. The whole synthetic route of the raw materials are cheap and easy to obtain, the process of synthesis of few, simple operation, low operation cost, process and environmental protection, it is very suitable for industrial production, has a very high industrial application value. (by machine translation)

Huisgen cycloaddition with acetylene gas by using an amphiphilic self-assembled polymeric copper catalyst

A copper-mediated Huisgen cycloaddition, aka the copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC), of flammable acetylene gas and a variety of organic azides proceeded smoothly by using our amphiphilic self-assembled polymeric copper catalyst MPPI-C

Palladium-catalyzed oxidative C-H/C-H cross-coupling of 1-substituted 1,2,3-triazoles with furans and thiophenes

Palladium-catalyzed heteroarylation of 1-substituted 1,2,3-triazoles with furans and thiophenes has been developed in the presence of pyridine and Ag2CO3. The procedure is suitable for the regioselective preparation of 1,5-disubstitu

Phase-Vanishing Method with Acetylene Evolution and Its Utilization in Several Organic Syntheses

A novel quadraphasic phase-vanishing system in which acetylene is evolved from calcium carbide and directly applied in situ to the Sonogashira coupling reaction was developed. This method, which provides a safe, convenient, and one-pot means to utilize gaseous reagents without special equipment, was also applied to a Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and a three-component aldehyde-alkyne-amine (A3) coupling reaction with excellent results. (Figure Presented).

Synthesis of thermally stable energetic 1,2,3-triazole derivatives

Various thermally stable energetic polynitro-aryl-1,2,3-triazoles have been synthesized through Cu-catalyzed [3+2] cycloaddition reactions between their corresponding azides and alkynes, followed by nitration. These compounds were characterized by analyti

Microwave irradiation as an effective means of synthesizing uninfstituted N-linked 1,2,3-triazoles from vinyl acetate and azides

N-Linked 1,2,3-triazoles have been prepared by a reaction of azides with vinyl acetate under microwave irradiation. Additionally, a microwave-assisted, two-step, one-pot procedure from halides involving azideinfstitution in diethyl ether, followed by -reaction with vinyl acetate, has effectively been employed. Georg Thieme Verlag Stuttgart - New York.

Azoles. Part 13. Synthesis and bromine → lithium exchange reactions of some 1-substituted 4,5-dibromo-1H-1,2,3-triazoles and 2-substituted 4,5-dibromo-2H-1,2,3-triazoles

4,5-Dibromo-1H-1,2,3-triazole was synthesised by various routes and reacted with chloromethyl methyl ether (N-1/2), methyl chloroformate (N-1), benzyl chloride (N-1), 4-methoxybenzyl chloride (N-1), 4-nitrobenzyl chloride (N-1/2) or triphenylmethyl chloride (N-2) under various conditions, to give isolable products substituted at the N-atoms shown in parentheses. 4,5-Dibromo-1-methoxymethyl-1H- and -2-methoxymethyl-2H-1,2,3-triazole reacted with butyllithium (in diethyl ether or tetrahydrofuran at low temperatures) at position-5 and the resulting lithiated derivatives were quenched with aqueous ammonium chloride, carbon dioxide, methyl chloroformate, benzophenone or dimethyl or diphenyl disulfide to give high yields (71-93%) of the corresponding 5-substituted 1,2,3-triazole. 1-Benzyl-4,5-dibromo-1H-1,2,3-triazole was converted similarly into 1-benzyl-4-bromo-5-methylsulfanyl-1H-1,2,3-triazole (91.5%). In a 'one pot' sequence and through two successive treatments with butyllithium and the appropriate quenching reagent (Ph2S2 and H2O), 4,5-dibromo-2-methoxymethyl-2H-1,2,3-triazole was converted similarly into 2-methoxymethyl-4-phenylsulfanyl-2.ff-1,2,3-triazole (47% yield).

Preparation of 1-hydroxypyrazoles and 1-hydroxy-1,2,3-triazoles by dealkylation of pyrazole and triazole N-oxides

1-Hydroxypyrazoles were obtained from 2-benzylpyrazole 1-oxides by debenzylation with iodotrimethylsilane. 1-Hydroxy-1,2,3-triazoles were achieved from 2-benzyltriazole 1-oxides by debenzylation effected with conc. hydrobromic acid or from 2- or 3-p-methoxybenzyltriazole 1-oxides by de-p methoxybenzylation accomplished by treatment with conc. sulfuric acid. 1-Methoxy-1,2,3-triazole was obtained by de-p-methoxybenzylation of 1-methoxy-3-p-methoxybenzyl-1,2,3-triazolium tetrafluoroborate accomplished by treatment with conc. sulfuric acid. 1-Hydroxypyrazole was selectively N-benzylated in absence of base to give 2-benzylpyrazole 1-oxide which, upon selective substitution at the 3-position and subsequent debenzylation, produced 3-substituted 1-hydroxypyrazole. Acta Chemika Scandinavica 1996.