2746-36-3

Upstream product

• 101117-42-4 benzoic acid-(N'-[2]quinolyl-hydrazide) 
• 91-22-5 quinoline 
• 59635-52-8 N-(phenylsulfonyl)benzohydrazonoyl chloride 
• 76226-71-6 N-[1-Phenyl-1-piperidin-1-yl-meth-(Z)-ylidene]-N'-quinolin-2-yl-hydrazine 
• 76226-69-2 N-[1-Morpholin-4-yl-1-phenyl-meth-(Z)-ylidene]-N'-quinolin-2-yl-hydrazine 
• 15793-77-8 2-hydrazinoquinoline 
• 100-52-7 benzaldehyde 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 611-73-4 Benzoylformic acid 
• 614-21-1 2-nitroacetophenone 

Relevant academic research and scientific papers

The Preparation of 3-Phenyltriazolopyridines and Their Benzologs from N-(Phenylsulfonyl)benzohydrazonoyl Chloride and Pyridines

3-Phenyltriazolopyridines were obtained in good yields from N'-benzenesulfonohydrazidates, generated from 2-unsubstituted pyridines and N-(phenylsulfonyl)benzohydrazonoyl chloride (2), by oxidation with chloranil.The reaction of quinoline and isoquinoline with 2 gave 1-phenyl-3-phenylsulfonyl-3,3a-dihydrotriazoloquinoline and 3-phenyl-1-phenylsulfonyl-1,10b-dihydrotriazoloisoquinoline respectively, both in good yields; they aromatized to the corresponding triazoles by the 1,2-elimination of benzenesulfinic acid on heating.

Nitroalkanes as electrophiles: Synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity

We discovered a reaction of nitroalkanes with 2-hydrazinylquinolines, 2-hydrazinylpyridines and bis-2,4-dihydrazinylpyrimidines in polyphosphoric acid (PPA) affording 1,2,4-triazolo[4,3-a]quinolines, 1,2,4-triazolo[4,3-a]pyridines and bis[1,2,4]triazolo[4,3-a:4′,3′-c]pyrimidines, respectively. The reaction expands the scope of heterocyclic annulations involving phosphorylated nitronates, believed to be the electrophilic intermediates formed from nitroalkanes in PPA. Several of the synthesized triazoles showed promising anticancer activity by inducing differentiation in neuroblastoma cancer cells. Due to the urgent need for novel differentiation agents for neuroblastoma therapy, this finding warrants further evaluation of this class of compounds against neuroblastoma.

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.

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.

Synthesis method of 1,2,4-triazolohetercyclic compound

The invention provides a method for synthesizing a 1,2,4-triazolohetercyclic compound. The method comprises the following steps: dissolving a 2-hydrazinohetercyclic compound (I) and an aldehyde compound (II) into acetonitrile A; stirring at 25 DEG C to 80

I2-TBHP-catalyzed one-pot highly efficient synthesis of 4,3-fused 1,2,4-triazoles from: N -tosylhydrazones and aromatic N-heterocycles via intermolecular formal 1,3-dipolar cycloaddition

I2-TBHP-catalyzed azomethine imine generation and subsequent regioselective 1,3-dipolar cycloaddition (DC) with aromatic N-heterocycles was developed to afford various 4,3-fused 1,2,4-triazoles in excellent yields. The method is operationally simple and highly efficient with broad functional group tolerance.

Synthesis of 1,2,4-Triazolo[4,3-a]pyridines and Related Heterocycles by Sequential Condensation and Iodine-Mediated Oxidative Cyclization

A facile and efficient approach to access 1,2,4-triazolo[4,3-a]pyridines and related heterocycles has been accomplished through condensation of readily available aryl hydrazines with corresponding aldehydes followed by iodine-mediated oxidative cyclizatio

Palladium-catalyzed coupling of aldehyde-derived hydrazones: Practical synthesis of triazolopyridines and related heterocycles

The palladium-catalyzed intermolecular coupling of aldehyde-derived hydrazones with chloroazines, followed by oxidative cyclization under mild conditions afforded access to a broad variety of bicyclic heterocyclic scaffolds (see scheme) that have potentia

STUDIES ON THIOAMIDES AND THEIR DERIVATIVES. PART II. REACTION OF QUATERNARY SALTS OF N,N-DISUBSTITUTED THIOAMIDES WITH 2-HYDRAZINOQUINOLINE

In reactions of methyliodides of N,N-disubstituted thioamides with 2-hydrazinoquinoline a series of new compounds have been obtained: iodohydrides, derivatives of 1-α-morpholinobenzylidene-2-quinolinohydrazine and of 1-α-piperidinobenzylidene-2-quinolinohydrazine.The compounds obtained, when transformed into free bases, undergo cyclization to derivatives of s-triazolo(4,3-a)quinoline system under the effect of glacial acetic acid.All these compounds have been characterized by means of UV and IR spectra.