274-59-9

Basic information

• Product Name: 1,2,3-TRIAZOLO(1,5-A)PYRIDINE
• Synonyms: 1,2,3-TRIAZOLO(1,5-A)PYRIDINE;triazolo[1,5-a]pyridine
• CAS NO: 274-59-9
• Molecular Formula: C₆H₅N₃
• Molecular Weight: 119.12
• Mol File: 274-59-9.mol

Chemical Properties

• Melting Point: 39-40 C
• Boiling Point: 106-109 °C(Press: 0.6 Torr)
• Appearance: /
• Density: 1.29 g/cm³
• Refractive Index: 1.689
• PKA: 1.17±0.30(Predicted)
• CAS DataBase Reference: 1,2,3-TRIAZOLO(1,5-A)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-TRIAZOLO(1,5-A)PYRIDINE(274-59-9)
• EPA Substance Registry System: 1,2,3-TRIAZOLO(1,5-A)PYRIDINE(274-59-9)

Safety Data

• Hazard Codes: Xi,C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• Hazardous Substances Data: 274-59-9(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
1,2,3-Triazolo(1,5-a)pyridine is utilized as a heterocyclic scaffold for the development of new pharmaceutical compounds. Its unique structure allows for the creation of molecules with potential therapeutic applications, making it a valuable component in the design of novel drugs.
Used in Drug Design and Synthesis:
1,2,3-Triazolo(1,5-a)pyridine serves as a key building block in the synthesis of complex molecules with potential medicinal properties. Its presence in a molecule can influence the molecule's biological activity, making it an important component in the development of new drugs with improved efficacy and selectivity.
Used in Chemical Research:
1,2,3-Triazolo(1,5-a)pyridine is employed as a model compound in the study of heteroaromatic compounds' chemical properties and reactivity. Understanding the behavior of this compound can provide insights into the broader class of heteroaromatic compounds and contribute to the advancement of organic chemistry.

InChI:InChI=1/C6H5N3/c1-2-4-9-6(3-1)5-7-8-9/h1-5H

Upstream product

• 78539-98-7 (E)-pyridin-2-ylmethylene-hydrazine 
• 22353-29-3 4-methyl-N'-(pyridin-2-ylmethylene)benzenesulfonohydrazide 
• 1121-60-4 pyridine-2-carbaldehyde 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 109-06-8 α-picoline 
• 1658-42-0 methyl 2-pyridylacetate 
• 87838-56-0 triazolo<1,5-a>pyridine-3-carboxylic acid 
• 25976-65-2 2-pyridinecarboxaldehyde hydrazone 
• 82315-59-1 4-nitrophenyl([1,2,3]triazolo[1,5-a]pyridin-7-yl)methanol 

Downstream Products

• 96461-37-9 3,5-dinitro-benzoic acid-[2]pyridylmethyl ester 
• 1007-49-4 2-pyridylmethyl acetate 
• 66310-15-4 pyridin-2-ylmethyl benzoate 
• 104294-19-1 pyridin-2-ylmethoxybenzene 
• 70415-71-3 4-nitrobenzoic acid 2-pyridinylmethyl ester 
• 77134-22-6 diphenyl(triazolopyridin-7-yl)methanol 
• 77134-21-5 1-(triazolopyridin-7-yl)cyclohexanol 
• 82315-59-1 4-nitrophenyl([1,2,3]triazolo[1,5-a]pyridin-7-yl)methanol 
• 77134-19-1 phenyl([1,2,3]triazolo[1,5-a]pyridin-7-yl)methanol 
• 77134-20-4 α-(triazolopyridin-7-yl)-4-methoxybenzyl alcohol 
• 128017-46-9 2-(2-Oxo-2-phenyl-ethyl)-[1,2,3]triazolo[1,5-a]pyridin-2-ium; bromide 
• 1121-60-4 pyridine-2-carbaldehyde 
• 586-98-1 2-Hydroxymethylpyridine 
• 4377-35-9 α,α-dichloropicoline 

Relevant articles and documents

Aerial oxidation of some 2-pyridyl ketone hydrazones catalyzed by Cu2+. Physical properties of reaction products

Some 2-pyridyl ketone hydrazones were subjected to aerial oxidation catalyzed by Cu2+. The oxidation product of di-2-pyridyl ketone hydrazone had the structure of a derivative of [1,2,3]-triazolo[1,5-a]pyridine, and this structure is different from that previously proposed by other investigators. The fluorescence spectra of the oxidation products were measured in solutions of a wide pH range. In contrast to the oxidation products of other 2-pyridyl ketone hydrazones, that of di-2-pyridyl ketone hydrazone showed very strong fluorescence in acidic media. The characteristic nature of this compound was also apparent in the ultraviolet spectrum. The generation of hydroxyl radical was demonstrated in the aerial oxidation of di-2-pyridyl ketone hydrazone catalyzed by Cu2+, suggesting the formation of hydrogen peroxide as another oxidation product.

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

Transannulation of Pyridotriazoles with Naphthoquinones and Indoles: Synthesis of Benzo[f]Pyrido[1,2-a]Indoles and Indolizino[3,2-b]indoles

Ruthenium catalysed denitrogenative transannulation of pyridotriazoles with naphthoquinones provided the transannulated benzo[f]pyrido[1,2-a]indoles derivatives in good to excellent yields. While pyridotriazoles with indoles in presence of PivOH and oxone yield indolizino[3,2-b]indoles under metal-free conditions. Quinone annulation proceeds through ruthenium-carbenoid intermediate while indole annulation may proceed via a diazo-pyridinium intermediate. Control experiments suggest that both the transformations follow the ionic mechanism. (Figure presented.).

Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones

A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed. This transformation provides a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.

Nitrous oxide as a diazo transfer reagent: The synthesis of triazolopyridines

Nitrous oxide is a potential diazo transfer reagent, but its applications in organic chemistry are scarce. Here, we show that triazolopyridines and triazoloquinolines are formed in the reactions of metallated 2-alkylpyridines or 2-alkylquinolines with N2O. The reactions can be performed under mild conditions and give synthetically interesting triazoles in moderate to good yields.

Triazolopyridazine derivative as well as preparation method, pharmaceutical composition and application thereof

The invention relates to triazolopyridazine derivatives as well as a preparation method, a pharmaceutical composition and application thereof. The invention provides a compound shown in a general formula (I), cis-trans isomers, enantiomers, diastereoisomers, racemes, solvates, hydrates or pharmaceutically acceptable salts or prodrugs of the compound, and a preparation method of the compound, the cis-trans isomers, the enantiomers, the diastereoisomers, the racemes, the solvates, the hydrates or the pharmaceutically acceptable salts or the prodrugs of the compound; preparation method thereof; pharmaceutical compositions containing the compounds, and the use of the compounds as alpha 5-GABAA receptor modulators, wherein R 1, R 2, and Z are as defined in the specification. pharmaceutical compositions containing the compounds and application of the compounds as alpha-5-GABAA receptor modulators, wherein R1, R2 and Z are as defined in the specification.

Method for synthesizing [1,2,3]triazole[1,5-a]pyridines compound through non-catalyst N-N coupling reaction

The invention relates to a method for synthesizing [1,2,3]triazole[1,5-a]pyridines compound through non-catalyst N-N coupling reaction. The invention discloses an efficient method for synthesizing a product at one step without using a catalyst under a mild condition from a 2-pyridylamine compound and nitroso tert-butyl ester as a mild nitrogen atom source. The method is free from the catalyst, thereaction step is reduced, the condition is extremely mild, the efficiency is high, and the later modification can be performed on the biological active molecular, thereby facilitating the industrialproduction of [1,2,3]triazole[1,5-a]pyridines compound.

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.

Cobalt(II)-based Metalloradical Activation of 2-(Diazomethyl)pyridines for Radical Transannulation and Cyclopropanation

A new catalytic method for the denitrogenative transannulation/cyclopropanation of in-situ-generated 2-(diazomethyl)pyridines is described using a cobalt-catalyzed radical-activation mechanism. The method takes advantage of the inherent properties of a CoIII-carbene radical intermediate and is the first report of denitrogenative transannulation/cyclopropanation by a radical-activation mechanism, which is supported by various control experiments. The synthetic benefits of the metalloradical approach are showcased with a short total synthesis of (±)-monomorine.

Impact and importance of electrostatic potential calculations for predicting structural patterns of hydrogen and halogen bonding

The way in which differences in electrostatic potential values can govern how ditopic hydrogen/halogen-bond acceptors form supramolecular interactions in the solid state has been examined using two heterocycles, [1,2,3]triazalo-[3,5-α]quinoline and, [1,2,3]triazalo-[3,5-α]pyridine. In general, the better donor (as ranked by electrostatic potential values) preferentially binds to the acceptor atom that carries the higher electrostatic potential value but the outcome is crucially dependent on the magnitude of the potential-energy differences, and structural selectivity can be fine-tuned to generate specifically targeted supramolecular architectures. DFT calculations on [1,2,3]triazalo-[3,5-α]quinoline and [1,2,3]triazalo-[3,5-α]pyridine indicate that the differences in electrostatic potential between the competing sites on the molecules are 38 kJ mol-1 and 26 kJ mol-1, respectively. In order to establish how the nature of the electrostatic potential differences impact the structural landscape around these molecules both heterocycles were co-crystallized with twelve hydrogen-bond (HB) donors, five halogen-bond (XB) donors, and four mixed HB/XB donors. A total of 42 new co-crystals were obtained (as determined by IR spectroscopy), eight of which yielded crystals suitable for single-crystal X-ray diffraction. Results indicate that an electrostatic potential difference greater than 38 kJ mol-1 leads to a pronounced intermolecular preference for the best acceptor but no selectivity is obtained with a smaller difference. This study shows that electrostatic factors play important roles for defining the structural landscape around molecules capable of engaging in a numerous and competing intermolecular interactions as long as the difference between potentially competing sites is large enough.