64017-21-6

Upstream product

• 20743-49-1 2-methyl-5-phenyl-2H-tetrazole 
• 100-47-0 benzonitrile 
• 614-28-8 N-benzoylbenzamide 
• 302-15-8 methylhydrazine sulfuric acid 
• 32272-86-9 3,5-diphenyl-4-methyl-1,2,4-4H-triazole 
• 98-88-4 benzoyl chloride 
• 85636-46-0 N-methyl-N-(phenylsulfonyl)benzamidrazone 
• 85636-43-7 N-methyl-N-(phenylsulfonyl)benzohydrazonoyl chloride 
• 4194-36-9 N-<(Phenylthioxo)-methyl>benzamide 
• 60-34-4 methylhydrazine 
• 888-71-1 3,5-diphenyl-1,2,4-oxadiazole 
• 74-89-5 methylamine 
• 108-86-1 bromobenzene 
• 532-55-8 Benzoyl isothiocyanate 

Relevant academic research and scientific papers

Synthesis of multi-substituted 1,2,4-triazoles utilising the ambiphilic reactivity of hydrazones

The synthesis of N-alkyl-1H-1,2,4-triazoles from N,N-dialkylhydrazones and nitriles via formal [3+2] cycloaddition including the C-chlorination/nucleophilic addition/cyclisation/dealkylation sequence was developed. This sequential reaction utilising the in situ generation of hydrazonoyl chloride based on the ambiphilic reactivity of hydrazones afforded a variety of multi-substituted N-alkyl-triazoles in high yields. The synthetic utility of multi-substituted triazoles was also demonstrated by further transformations.

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.

Visible light-induced cyclization reactions for the synthesis of 1,2,4-triazolines and 1,2,4-triazoles

A novel method for concisely synthesizing 1,2,4-triazolines via [3+2] cyclization under visible light is reported. These compounds can be easily converted into 1,2,4-triazoles under basic or photoredox conditions. The application of the 1,2,4-triazoles was also investigated via mild operations.

Thermolysis of triazoles as melts - Is the 3,5-diphenyl-1,2,4-triazole group a good leaving group?

The mechanism of the rearrangement of 4-alkyltriazoles to the corresponding 1-alkyltriazoles on thermolysis at 330 °C is shown to involve initial formation of an intermediate 1,4-dialkyltriazolium triazolate salt. The triazolate ion subsequently attacks at the alkyl group bearing 1- and 4-positions of the dialkyltriazolium ion, yielding the observed products. No evidence for unimolecular reaction steps has been found. The triazole moiety in these compounds is only a weak leaving group, which requires activation by alkylation. Unimolecular reaction steps never take place, neither from neutral triazole species nor from activated dialkyl-substituted triazolium species.

Photoinduced molecular rearrangements. The photochemistry of some 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles. Formation of 1,2,4-triazoles, indazoles, and benzimidazoles

The photochemistry of some 3,5-disubstituted 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles [external, such as added amines or hydrazines, or internal, such as an o-aminophenyl moiety at C(3) of the oxadiazole ring] has been investigated. In the irradiation of 5-amino-(or 5-N-substituted amino) 3-phenyl-1,2,4-oxadiazoles in the presence of aliphatic primary amines (or ammonia), photolytic species arising from heterolytic cleavage of the ring O-N bond capture the nucleophilic reagent to give open-chain intermediates, which develop into 1,2,4-triazolin-5-ones. Similarly, irradiations of 3,5-diphenyl-, 3-methoxy-5-phenyl-, and 5-methyl-3-phenyl-1,2,4-oxadiazoles gave 1,2,4-triazoles. In the same context, irradiations of representative substrates in the presence of hydrazines have been also investigated. In the irradiation of 3-(o-aminophenyl)-5-methyl-, 3-[o-(methylamino)phenyl]-5-methyl-, and 3-(o-aminophenyl)-5-phenyl-1,2,4-oxadiazoles, concomitant formation of indazoles and benzimidazoles, presumably arising from a common photolytic species, has been observed. Some mechanistic aspects have been considered, and possible applications in synthesis have been pointed out.

Transition States in the Crystalline Phase? Thermal Rearrangements of Solid 4H-1,2,4-Triazoles

In the crystalline state the 4-methyl and 4-ethyl substituted 4H-1,2,4-triazoles were found to undergo thermal rearrangement to the corresponding 1-alkyl substituted triazoles.The same reaction took place in the melts.Reaction rates were measured in both

Substituent Effects in the Rearrangement of 4-Alkyl-4H-1,2,4-triazoles

A study of the thermal rearrangement of neat 4-alkyl-substituted 4H-1,2,4-triazoles to the corresponding 1-alkyl-1H-1,2,4-triazoles showed that the rearrangement was accompanied by formation of 3,5-diphenyl-1H-1,2,4-triazole and alkenes.The composition of

SYNTHESIS OF NITROGEN HETEROCYCLES FROM 1-METHYLTHIO-2-PHENYL-2-AZABUTA-1,3-DIENE-4,4-DICARBONITRILES

The reactions of title compounds with different nucleophiles afforded a simple method for a synthesis of pyrimidines, 1,2,4-triazoles, 1,2,4-oxadiazoles and 1,3,5-triazines.