2746-44-3

Usage

Type of compound

Heterocyclic compound

Structure

Contains a triazolopyridine ring system and a 4-methoxyphenyl substituent

Applications

Medicinal and pharmaceutical research as a potential drug candidate

Therapeutic uses

Potential applications in anti-inflammatory or anti-cancer agents

Importance

Valuable building block for the synthesis of novel chemical entities with potential biological activity

Upstream product

• 560101-31-7 (E)-N-(4-methoxybenzylidene)-N'-(2-pyridyl)hydrazine 
• 4930-98-7 pyrid-2-ylhydrazine 
• 302935-29-1 C₁₃H₁₃N₃O₂ 
• 109-09-1 2-chloropyridine 
• 54998-29-7 ethyl 4-methoxybenzimidate hydrochloride 
• 62437-99-4 2-hydrazinylpyridine dihydrochloride 
• 274-80-6 [1,2,4]triazolo[4,3-a]pyridine 
• 696-62-8 para-iodoanisole 
• 7099-91-4 p-methoxybenzoylformic acid 
• 637-69-4 4-Methoxystyrene 
• 110-86-1 pyridine 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 5874-09-9 methyl (4-methoxyphenyl)carbodithioate 

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.

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.

Facile one pot synthesis of N-fused 1,2,4-triazoles via oxidative cyclisation using DDQ

A facile and expedient one pot synthesis of N-fused 1,2,4-triazoles from 2-hydrazinopyridines or 2-hydrazinopyrazines and aldehydes is described via oxidative cyclization using DDQ as a safe and convenient oxidizing agent and polyethylene glycol as recyclable reaction medium. This protocol is effective toward various substrates having different functionalities. The easy recyclability of the reaction medium makes the process economic and potentially viable for commercial applications.

Facile one-pot synthesis of N-fused 1,2,4-triazoles via oxidative cyclization using manganese dioxide

[Figure not available: see fulltext.] 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 manganese dioxide to afford the desired products mostly in high yields and in relatively short times. The mild nature of the synthesis, cheap oxidizing agent, and short reaction time are notable advantages of the developed protocol. This protocol is effective toward various substrates having different functionalities.

One-pot synthesis of N-fused 1,2,4-triazoles and related heterocycles via I2/TBHP-mediated oxidative C–N bond formation

A metal-free iodine/TBHP-mediated oxidative C–N bond formation for the one-pot synthesis of N-fused 1,2,4-triazoles and related heterocycles via cyclization has been developed. This reaction which is amenable to scale-up affords the corresponding products with good to excellent yields and tolerates a wide range of functional groups.