87277-53-0

Upstream product

• 3357-42-4 3-phenyl-1,2,4-triazole 
• 104-88-1 4-chlorobenzaldehyde 
• 623-03-0 4-Cyanochlorobenzene 
• 1670-14-0 benzamidine monohydrochloride 
• 100-46-9 benzylamine 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 74-11-3 para-chlorobenzoic acid 
• 100-47-0 benzonitrile 
• 536-40-3 4-chlorobenzoic acid hydrazide 
• 1527-91-9 N-phenylbenzamidine 
• 6828-55-3 N'-benzoyl-4′-chlorobenzohydrazide 
• 613-94-5 benzoic acid hydrazide 
• 122-01-0 4-chloro-benzoyl chloride 
• 5033-28-3 4-chlorobenzamidoxime 

Downstream Products

• 87277-52-9 3-(4-Chloro-phenyl)-1-methyl-5-phenyl-1H-[1,2,4]triazole 
• 87277-51-8 1-methyl-5-(4-chlorophenyl)-3-phenyl-1H-1,2,4-triazole 

Relevant academic research and scientific papers

Iodine Catalyzed Oxidative Coupling of Diaminoazines and Amines for the Synthesis of 3,5-Disubstituted-1,2,4-Triazoles

A simple, convenient, transition metal-free one pot synthesis of 3,5-disubstituted-1,2,4-triazoles has been established. The innovation in this reaction is the use of easily available 1,1-diaminoazines as substrates. This method provides the products with wider substrate scope, at an expedited rate, and with relatively better yields in comparison to the reported methods. The reaction mechanism involves an initial intermolecular nucleophilic addition (facilitated by I2) followed by intramolecular nucleophilic cyclization.

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.

Development of novel liver?X?receptor modulators based on a 1,2,4-triazole scaffold

Liver X Receptor (LXR) agonists have been reported as a potential treatment for atherosclerosis, Alzheimer's disease and hepatitis C virus (HCV) infection. We have designed and synthesized a series of potent compounds based on a 1,2,4-triazole scaffold as novel LXR modulators. In cell-based cotransfection assays these compounds generally functioned as LXR agonists and we observed compounds with selectivity towards LXRα (7-fold) and LXRβ (7-fold) in terms of potency. Assessment of the effects of selected compounds on LXR target gene expression in HepG2 cells revealed that compounds 6a-b and 8a-b behaved as inverse agonists on FASN expression even though they were agonists in the LXRα and LXRβ cotransfection assays. Interestingly, these compounds had no effect on the expression of SREBP-1c confirming a unique LXR modulator pharmacology. Molecular docking studies and evaluation of ADME properties in-silico show that active compounds possess favorable binding modes and ADME profiles. Thus, these compounds may be useful for in vivo characterization of LXR modulators with unique profiles and determination of their potential clinical utility.

Synthetic method of asymmetric 1,2,4-triazole derivatives

The invention provides a synthetic method of asymmetric 1,2,4-triazole derivatives. The synthetic method comprises the following steps: mixing amidine compound hydrochloride, amidoxime compounds, copper oxide and potassium carbonate, adding an organic solvent, and carrying out heating reaction under the condition of stirring to obtain a product; drying, separating and purifying to obtain the asymmetric 1,2,4-triazole derivatives. Compared with the prior art, the synthetic method provided by the invention has the following advantages that firstly, the synthetic method is carried out in the air atmosphere, so that the cost is low; secondly, no precious metals, strong base and organic oxidants are used, while the copper oxide is used as a catalyst, so that the cost is reduced; thirdly, amidine and nitrile are used as reaction raw materials, and the raw materials are easily obtained; fourthly, the synthetic method is high in efficiency and wide in application range, and is suitable for multiple substrate reactions.

A 1, 2, 4-triazole derivative synthesis method

The invention provides a 1,2,4-triazole derivative and a preparation method thereof. The method comprises the following steps: after mixing amidine or o-aminopyridine with a nitrile compound, copper acetate monohydrate, phenanthroline and sodium carbonate, adding an organic solvent; reacting for 12-24 hours in air at 110-120 DEG C; extracting the obtained product by ethyl acetate; drying by anhydrous sodium sulfate; decompressing and concentrating to obtain a coarse product; carrying out column chromatography isolation to obtain the 1,2,4-triazole derivative. Compared with the prior art, the method provided by the invention has the advantages that (1) the method is carried out in an air atmosphere, so that the cost is low; (2) no noble metals, strong bases and organic oxidizing agents are used but copper acetate monohydrate is used as a catalyst, so that the cost is saved; (3) by using amine and nitrile as reaction raw materials, the raw materials are easy to obtain; (4) the synthetic method is high in efficiency, wide in using range and suitable for various substrate reactions.

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.

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.

Regioselectivity in the thermal rearrangement of unsymmetrical 4-methyl-4H-1,2,4-triazoles to 1-methyl-1H-1,2,4-triazoles

The rearrangement of 4-methyl-3,5-diaryl-4H-1,2,4-triazoles to the corresponding 1-methyl-3,5-diaryl-1H-1,2,4-triazoles showed regioselectivity comparable to that observed for the alkylation of 3,5-diaryl-1H-1,2,4-triazoles. This lends support to a proposed mechanism for the rearrangement that involves consecutive nucleophilic displacements steps.