54856-82-5

Usage

Uses

Used in Pharmaceutical Research:
3-Methyl-1,2,3-triazolo(1,5-a)pyridine is used as a compound of interest in pharmaceutical research for its potential properties. Its triazolo structure suggests that it may have applications in the development of new drugs, although more research is needed to fully understand its capabilities and potential uses in this field.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-Methyl-1,2,3-triazolo(1,5-a)pyridine is used as a building block or intermediate in the creation of more complex molecules. Its unique structure allows for the formation of various chemical bonds, making it a valuable component in the synthesis of a wide range of compounds.
Used in Material Science:
3-Methyl-1,2,3-triazolo(1,5-a)pyridine may also find applications in material science, where its properties could be utilized to develop new materials with specific characteristics. Its potential use in this field is still under investigation, but its unique structure and properties make it a promising candidate for future material development.

InChI:InChI=1/C7H7N3/c1-6-7-4-2-3-5-10(7)9-8-6/h2-5H,1H3

Upstream product

• 59742-91-5 (E)-2-(1-hydrazineylideneethyl)pyridine 
• 97-63-2 methyl methacrylate 
• 140870-08-2 C₁₅H₁₃N₃O 
• 113385-65-2 3-methyl-7-trimethylsilyltriazolopyridine 
• 128017-41-4 2-Methoxycarbonylmethyl-3-methyl-[1,2,3]triazolo[1,5-a]pyridin-2-ium; bromide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 128017-42-5 2-Ethoxycarbonylmethyl-3-methyl-[1,2,3]triazolo[1,5-a]pyridin-2-ium; bromide 
• 128017-43-6 3-Methyl-2-(2-oxo-2-phenyl-ethyl)-[1,2,3]triazolo[1,5-a]pyridin-2-ium; bromide 
• 1122-62-9 2-acetylpyridine 
• 69045-79-0 2-choro-5-iodopyridine 
• 726666-49-5 2-(3-methyl-7-[1,2,3]triazolo[1,5-a]pyridyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane 
• 766-11-0 5-bromo-2-fluoropyridine 
• 15854-87-2 4-iodopyridine 
• 696-62-8 para-iodoanisole 

Downstream Products

• 128017-49-2 3-Methyl-2-(1-methyl-2-oxo-2-phenyl-ethyl)-[1,2,3]triazolo[1,5-a]pyridin-2-ium; bromide 
• 128017-43-6 3-Methyl-2-(2-oxo-2-phenyl-ethyl)-[1,2,3]triazolo[1,5-a]pyridin-2-ium; bromide 
• 1122-62-9 2-acetylpyridine 
• 20988-55-0 1-(pyridine-2-yl)ethanol 
• 100-69-6 2-vinylpyridine 
• 10445-92-8 2-(1-chloroethyl)pyridine 
• 127-63-9 diphenyl sulphone 
• 2116-62-3 2-(2-phenylethyl)pyridine 
• 882-33-7 diphenyldisulfane 
• 103-79-7 1-phenyl-acetone 
• 1094674-60-8 (3-methyl-[1,2,3]triazolo[1,5-a]pyridin-7-yl)(3,4,5-trimethoxyphenyl)methanol 
• 1384956-03-9 (E)-7-(1,2-diphenylvinyl)-3-methyl-[1,2,3]triazolo[1,5-a]pyridine 
• 15260-65-8 2-(1-phenylvinyl)pyridine 
• 74309-54-9 2-[1-(2-tolyl)-vinyl]pyridine 

Relevant academic research and scientific papers

TBAB-Catalyzed Csp3–N Bond Formation by Coupling Pyridotriazoles with Anilines: A New Route to (2-Pyridyl)alkylamines

A new metal-free procedure allowing Csp3–N bond formation through coupling of pyridotriazoles and weakly nucleophilic anilines has been developed. This sustainable reaction shows high tolerance towards functional groups (ketones, free alcohols) leading to 2-picolylamine derivatives. The key to our success is the use of a catalytic amount of TBAB and water as a co-solvent leading to the formation of pyridylalkylamine derivatives. As this coupling tolerates the presence of Csp2–Br bond on both partners of the reaction, we performed a sequential one-pot reaction between functionalized triazolopyridines and anilines followed by a second coupling with N-tosylhydrazones leading to the formation of Csp3–N and Csp2–Csp2 bonds.

Recyclable Heterogeneous Copper(II)-Catalyzed Oxidative Cyclization of 2-Pyridine Ketone Hydrazones towards [1,2,3]Triazolo[1,5-a]pyridines

The heterogeneous copper(II)-catalyzed oxidative cyclization of 2-pyridine ketone hydrazones was achieved in ethyl acetate at room temperature in the presence of an MCM-41-anchored bidentate 2-aminoethylamino copper(II) catalyst [MCM-41-2N-Cu(OAc) 2

Safe and Facile Access to Nonstabilized Diazoalkanes Using Continuous Flow Technology

Despite the high synthetic potential of nonstabilized diazo compounds, their utilization has always been hampered by stability, toxicity, and safety issues. The present method opens up access to the most reactive nonstabilized diazoalkanes. Among diazo compounds, nonstabilized alkyl diazo compounds are the least represented because of their propensity to degrade during preparation. The continuous flow oxidation process of hydrazones on a silver oxide column afforded an output stream of base- and metal-free pure diazo solution in dichloromethane. Starting from innocuous ketones and aldehydes, this methodology allows the production of a broad range of unprecedented diazoalkanes compounds in excellent yields, while highlighting their synthetic potential and the possibility of safe large-scale diazo production.

Palladium-Catalyzed Divergent Arylation with Triazolopyridines: One-Pot Synthesis of 6-Aryl-2-α-styrylpyridines

We have developed a new strategy for palladium-catalyzed arylation reactions with triazolopyridines, wherein two different chemical transformations (C-3 vs. C-7) are observed by differentiating the substrates using different bases. The reactive palladium carbenoids were directly generated from triazolopyridines and underwent denitrogenative arylations with aryl bromides. Intriguingly, when potassium carbonate was replaced with potassium tert-butoxide, direct C-H arylation occurred at the most acidic position (C-7). Moreover, two different catalytic arylation events were successfully performed in a one-pot sequence, providing a convenient access to 6-aryl-2-α-styrylpyridines.

Facile one-pot synthesis of [1,2,3]triazolo[1,5-a]pyridines from 2-acylpyridines by copper(II)-catalyzed oxidative N-N bond formation

An efficient and simple method for the synthesis of various [1,2,3]triazolo[1,5-a]pyridines has been established. The method involves a copper(II)-catalyzed oxidative N-N bond formation that uses atmospheric oxygen as the terminal oxidant following hydrazonation in one pot. The use of ethyl acetate as the solvent dramatically promotes the oxidative N-N bond-formation reaction and enables the application of oxidative cyclization in the efficient one-pot reaction. A mechanism for the reaction was proposed on the basis of the results of a spectroscopic study. In the same pot: [1,2,3]Triazolo[1,5-a] pyridines are synthesized from the corresponding 2-acylpyridines by a one-pot method, consisting of hydrazonation followed by oxidative cyclization through copper(II)-catalyzed N-N bond formation (see scheme).

Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: A general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines

A general and efficient NH insertion reaction of rhodium pyridyl carbenes derived from pyridotriazoles was developed. Various NH-containing compounds, including amides, anilines, enamines, and aliphatic amines, smoothly underwent the NH insertion reaction to afford 2-picolylamine derivatives. The developed transformation was further utilized in a facile one-pot synthesis of imidazo[1,5-a]pyridines.

Triazolopyridines. Part 29. Direct arylation reactions with [1,2,3]triazolo[1,5-a]pyridines

[1,2,3]Triazolo[1,5-a]pyridine reacts with aryl halides in presence of catalytic amounts of Pd(OAc)2 and PPh3 in DMF to give, in medium or low yield, direct arylations in C3 and pyridyl aryl ketones. Thiazole and benzothiazole have been directly arylated using 7-halotriazolopyridines. These behaviours are unprecedented in the chemistry of [1,2,3]triazolo[1,5-a] pyridines. ARKAT-USA, Inc.

Ni-catalyzed alkenylation of triazolopyridines: Synthesis of 2,6-disubstituted pyridines

A synthetic strategy to access 2,6-disubstituted pyridines from triazolopyridines through a regioselective nickel-catalyzed alkenylation reaction of the C7-H bond is described. The N2 fragment embedded in the resulting C-H functionalized triazolopyridine can be readily excised using acidic or oxidative conditions to unmask the pyridine.

Synthesis of novel triazolopyridylboronic acids and esters. Study of potential application to Suzuki-type reactions

This paper describes a general method for the synthesis of novel [1,2,3]triazolo[1,5-a]pyridylboronic acids and esters, and the first results on Suzuki cross-coupling reactions with these new compounds and [1,2,3]triazolo[5,1-a]isoquinolylboronic acid, re

Regiospecific solid-phase synthesis of substituted 1,2,3-triazoles

A traceless and regiospecific solid-phase synthesis of substituted 1,2,3-triazoles is developed using polystyrene-sulfonyl hydrazide resin. The chemistry is applicable to combinatorial library synthesis.