778-65-4

Usage

Class

Triazolopyridine compounds

Structural feature

Phenyl group attached at the 3-position of the pyridine ring

Field of application

Medicinal chemistry

Potential therapeutic applications

Exhibits biological activity against certain enzymes and receptors

Significance

Promising candidate for the development of new pharmaceutical drugs

Research interest

Unique structure and properties make it an interesting target for further research in organic synthesis and chemical biology

InChI:InChI=1/C12H9N3/c1-2-6-10(7-3-1)12-14-13-11-8-4-5-9-15(11)12/h1-9H

Upstream product

• 41214-53-3 N′-(pyrid-2-yl)benzohydrazide 
• 110-86-1 pyridine 
• 21945-40-4 2-[(2E)-2-benzylidenehydrazinyl]pyridine 
• 75-05-8 acetonitrile 
• 4930-98-7 pyrid-2-ylhydrazine 
• 65-85-0 benzoic acid 
• 100-52-7 benzaldehyde 
• 98-88-4 benzoyl chloride 
• 2719-73-5 2-(2-benzylidenehydrazinyl)pyridine 
• 109-09-1 2-chloropyridine 
• 274-80-6 [1,2,4]triazolo[4,3-a]pyridine 
• 591-50-4 iodobenzene 
• 13939-06-5 molybdenum hexacarbonyl 
• 2168-78-7 methyl dithiobenzoate 

Downstream Products

• 89569-61-9 3-phenyl-5,6,7,8-tetrahydro-1,2,4-triazolo<4,3-a>pyridine 

Relevant academic research and scientific papers

TBAI/TBHP-Catalyzed Synthesis of [1,2,4]Triazolo[4,3-a]pyridines and 3,5-Diaryl-1,2,4-oxadiazoles via Oxidative Cleavage of C=C Double Bond

Abstract: A simple and efficient protocol has been described for the synthesis of [1,2,4]triazolo[4,3-a]pyri-dines and 3,5-disubstituted-1,2,4-oxadiazoles by reacting 2-hydrazinylpyridine and benzamidoximes, respec-tively, with styrenes via TBAI/TBHP-mediated oxidative cleavage of C=C bond under ligand- and metal-free conditions.

Metal free [4+1] and [5+1] annulation reactions to prepare heterocycles using DMF and its derivatives as one-carbon source

1,2,4-Triazolo[3,4-a]pyridines and related heterocycles and substituted triazines were commonly discovered scaffolds in a variety of pharmaceutical and agrochemical agents. Herein, we report a highly efficient and practical method using DMF and its derivative for the [4+1] and [5+1] annulation reactions to prepare these heterocycles. This metal free reaction takes advantages of shelf stable DMF as solvent and carbon donor, imidazole chloride as a catalyst, the mild reaction condition tolerates a broad substrate range and substitutes. The prepared 3-unsubstituted 1,2,4-triazolo[3,4-a]pyridine and derivatives allow further introduction of a variety of functional group1 at 3-position.

A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation

Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems.

Synthesis method for 1,2,4-triazolopyridine derivative

The invention provides a novel synthesis method for a 1,2,4-triazolopyridine derivative. According to the invention, the 1,2,4-triazolopyridine derivative can be obtained by taking a 2-pyridine hydrazone derivative and sodium hypochlorite as main synthesis raw materials through a reaction for 1-24 hours in an organic solvent at a temperature of 0-100 DEG C. The invention provides a synthetic method which is good in atom economy, mild in reaction conditions, simple and convenient to operate and easy to be controlled for the 1,2,4-triazolopyridine derivative.

Method for preparing 3-phenyl-[1,2,4] triazole [4,3-a] pyridine compound without metal catalysis

The invention discloses a method for preparing a 3-phenyl-[1,2,4] triazole [4,3-a] pyridine compound without metal catalysis. The method comprises the following steps: enabling a pyridine compound, sodium azide and a benzaldehyde compound to react suffici

A Convenient One-pot Synthesis of N-Fused 1,2,4-Triazoles via Oxidative Cyclization Using Trichloroisocyanuric Acid

A facile one-pot synthesis of N-fused 1,2,4-triazoles from heterocyclic hydrazines and aldehydes is reported. The reaction is efficiently promoted by trichloroisocyanuric acid to afford the desired products mostly in high yields and in relatively short time. The mild nature of the synthesis and short reaction time are notable advantages of the developed protocol. This protocol is effective toward various substrates having different functionalities.

A convenient one-pot synthesis of N-fused 1,2,4-triazoles via oxidative cyclization using chromium (VI) oxide

A facile one-pot synthesis of N-fused 1,2,4-triazoles from heterocyclic hydrazines and aldehydes is reported. The reaction is efficiently promoted by chromium (VI) oxide to afford the desired products mostly in high yields and in relatively short time. The high yield of the products and short reaction time are notable advantages of the developed protocol. This protocol is effective toward various substrates having different functionalities.

Electrochemical synthesis of 1,2,4-triazole-fused heterocycles

A reagent-free intramolecular dehydrogenative C-N cross-coupling reaction has been developed under mild electrolytic conditions. In this atom- and step-economical one-pot process, valuable 1,2,4-triazolo[4,3-a]pyridines and related heterocyclic compounds could be synthesized efficiently from commercially available aliphatic or (hetero)aromatic aldehydes and 2-hydrazinopyridines. Various functional groups are compatible with this metal- and oxidant-free protocol which can be carried out on a gram scale easily. This novel method was applied to the synthesis of one of the top-selling drugs Xanax and late stage functionalization for generating chemical diversity in biologically relevant lead molecules.

KI-catalyzed oxidative cyclization of α-keto acids and 2-hydrazinopyridines: Efficient one-pot synthesis of 1,2,4-triazolo[4,3-a] pyridines

A one-pot approach to substituted 1,2,4-triazolo[4,3-a]pyridines has been developed that is based on a KI-catalyzed oxidative cyclization of α-keto acids and 2-hydrazinopyridines. This transition-metal-free procedure was highly efficient and shows good economical and environmental advantages.

[1,2,4]-triazol [4,3-a] pyridines compound and synthesis method thereof

The invention discloses a [1,2,4]-triazol [4,3-a] pyridines compound and a synthesis method thereof. The compound has a structure general formula shown as the formula (I), wherein R1 is selected fromaryl and heterocyclic groups; R2 is selected from hydrogen, alkyl, alkoxy, halogen or aryl. According to the synthesis method, alpha-ketonic acid and 2-hydrazinopyridine are used as raw materials; KIis used as a catalyst; Na2CO3 is used as alkali; TBHP is used as an oxidizing agent; 1,4-dioxane is used as a solvent; after a series of serial connection cyclization and decarboxylation aromatization, the [1,2,4]-triazol [4,3-a] pyridines compound is obtained. The [1,2,4]-triazol [4,3-a] pyridines compound is prepared under the condition of no transition metal and has the advantages that the reaction is efficient and fast; the conditions are mild; the substrate is simple and can be easily obtained; the applicability is wide; the reaction time is short; the yield is high, and the like; meanwhile, the post treatment of the reaction is simple and convenient; the harm to experiment operators is reduced; the environment-friendly effect is achieved; the green chemical requirements are met.