4057-66-3

Usage

Chemical class

Triazole compounds

Structure

A triazole ring with 3-(4-nitrophenyl) and 5-phenyl substituents

Applications

Building block in the synthesis of pharmaceuticals and agrochemicals

Biological activities

Anti-tumor, anti-inflammatory, and antimicrobial properties

Metal ion interaction

Acts as a ligand for various metal ions

Usefulness in

Coordination chemistry and catalysis

Upstream product

• 1670-14-0 benzamidine monohydrochloride 
• 619-72-7 4-nitrobenzonitrile 
• 24461-61-8 (R)-Phenylglycine methyl ester 
• 122-04-3 4-nitro-benzoyl chloride 
• 3357-42-4 3-phenyl-1,2,4-triazole 
• 555-16-8 4-nitrobenzaldehdye 
• 28819-30-9 benzohydrazonamide 
• 6310-10-7 4-nitrobenzaldehyde hydrazone 
• 825-60-5 benzimidic acid ethyl ester 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 41981-24-2 methyl benzenecarbimidothioate hydroiodide 
• 100-47-0 benzonitrile 

Relevant academic research and scientific papers

TBHP/TBAI–Mediated simple and efficient synthesis of 3,5-disubstituted and 1,3,5-trisubstituted 1H-1,2,4-triazoles via oxidative decarbonylation of aromatic aldehydes and testing for antibacterial activities

The author has developed a simple, efficient and eco–friendly convenient general method for synthesis of 3,5–disubstituted–1,2,4–triazoles and 1,3,5–trisubstituted–1,2,4–triazoles from 3–monosubstituted–1,2,4–triazoles and 1,3–disubstituted–1,2,4–triazoles respectively using tetrabutylammonium iodide (TBAI) as catalyst and TBHP as oxidant under mid reaction conditions. This method provides structurally diverse 3,5–disubstituted 1,2,4–triazoes and 1,3,5––trisubstituted–1,2,4–triazoles in good to excellent yields. 3,5–Disubstituted 1,2,4–triazoes and 1,3,5––trisubstituted–1,2,4–triazoles derivatives are biologically and pharmaceutically active molecules, and therefore, this protocol could be of wide applications in medicinal chemistry and organic chemistry.

Green aqueous synthesis and antimicrobial evaluation of 3,5-disubstituted 1,2,4-triazoles

[Figure not available: see fulltext.] An eco-friendly and simple procedure was proposed for the synthesis of 3,5-disubstituted 1,2,4-triazoles by optimized reaction of benzamidine hydrochloride and various aryl hydrazides. H2O and K2

Synthesis of 5-aryl-3-C-glycosyl- and unsymmetrical 3,5-diaryl-1,2,4-triazoles from alkylidene-amidrazones

Among 1,2,4-triazole derivatives with versatile biological activities 3-C-glucopyranosyl-5-substituted-1,2,4-triazoles belong to the most efficient inhibitors of glycogen phosphorylase, and are thus potential antidiabetic agents. In seeking new synthetic methods for this class of compounds oxidative ring closures of N1-alkylidene carboxamidrazones were studied. O-Peracylated N1-(β-d-glycopyranosylmethylidene)-arenecarboxamidrazones were prepared from the corresponding glycosyl cyanides and amidrazones by Raney-Ni reduction in the presence of NaH2PO2. Bromination of the so obtained compounds by NBS gave hydrazonoyl bromide type derivatives which were ring closed to 3-C-glycosyl-5-substituted-1,2,4-triazoles in pyridine or by NH4OAc in AcOH. Under the same conditions O-perbenzoylated N1-arylidene-C-(β-d-glucopyranosyl)-formamidrazones gave the expected 1,2,4-triazoles as minor products only. N1-Arylidene-arenecarboxamidrazones were also transformed into 3,5-diaryl-1,2,4-triazoles with NBS/NH4OAc in AcOH indicating high functional group tolerance and general applicability of the method.

An efficient and recyclable heterogeneous catalytic system for the synthesis of 1,2,4-triazoles using air as the oxidant

Copper-zinc supported on Al2O3-TiO2 was found as a simple and efficient heterogeneous catalyst for the oxidative synthesis of 1,2,4-triazole derivatives using air as the green oxidant under ligand-, base- and additive-free conditions. The heterogeneous reactions carried out smoothly with a large range of substrates, including NO2-, vinyl-, pyrimidine- and imidazole-contained starting materials, and provided corresponding triazoles in moderate to excellent yields with low catalyst loading (1.6 mol%). Furthermore, the catalyst can be simply recycled many times without significant loss in catalytic activity. The Royal Society of Chemistry.

PEG-supported synthesis of 3,5-disubstituted 1,2,4-triazoles

1,3-Dipolar cycloadditions between diethyl azodicarboxylate and the polymer-bound munchnones generated from the corresponding carboxylic acids provided a library of 3,5-disubstituted 1,2,4-triazoles in excellent yield and high purity.

Solid phase synthesis of 1,2,4-triazoles under microwave irradiation

1,2,4-Triazoles (3a-g) have been prepared from three component condensation reaction of acid hydrazide (1), S-methyl isothioamide hydroiodide (2), and ammonium acetate on the surface of silica gel under microwave irradiation.