109299-75-4

Upstream product

• 288-36-8 1,2,3-triazole 
• 100-44-7 benzyl chloride 
• 555-96-4 Benzylhydrazine 
• 100-39-0 benzyl bromide 
• 288-36-8 1 ,2,3-Triazole 
• 109299-49-2 2-benzyl-1,2,3-triazole 1-oxide 

Downstream Products

• 1339958-80-3 2-benzyl-4-phenyl-2H-1,2,3-triazole 

Relevant academic research and scientific papers

Palladium-catalyzed ortho-C-H alkenylation of 2-benzyl-1,2,3-triazoles

A mild and efficient method for the direct alkenylation of 2-benzyl-1,2,3-triazoles via Pd-catalyzed C-H bond activation was developed. This protocol was compatible with various substrates and gave the corresponding products in good to excellent yields. Thus, the present study provides a novel and valuable method for the synthesis of 2-benzyl-1,2,3-triazole derivatives.

Synthesis and structure-activity relationship of 1- and 2-substituted-1,2,3-triazole letrozole-based analogues as aromatase inhibitors

A series of bis- and mono-benzonitrile or phenyl analogues of letrozole 1, bearing (1,2,3 and 1,2,5)-triazole or imidazole, were synthesized and screened for their anti-aromatase activities. The unsubstituted 1,2,3-triazole 10a derivative displayed inhibitory activity comparable with that of the aromatase inhibitor, letrozole 1. Compound 10a, bearing a 1,2,3-triazole, is also 10000-times more tightly binding than the corresponding analogue 25 bearing a 1,2,5-triazole, which confirms the importance of a nitrogen atom at position 3 or 4 of the 5-membered ring needed for high activity. The effect on human epithelial adrenocortical carcinoma cell line (H295R) proliferation was also evaluated. The compound 10j (IC50 = 4.64 μM), a letrozole 1 analogue bearing para-cyanophenoxymethylene-1,2,3-triazole decreased proliferation rates of H295R cells by 76 and 99% in 24 and 72 h respectively. Computer calculations, using quantum ab initio structures, suggest a possible correlation between anti-aromatase activity and the distance between the nitrogen in position 3 or 4 of triazole nitrogen and the cyano group nitrogen.

Method for producing 1-substituted-1,2,3- triazole derivative

A method for producing a compound of the formula: (1) in a secondary or tertiary alcohol in the presence of a base, or (2) in the absence of a base is provided. According to this method, a 1-substituted-1,2,3-triazole compound having a tyrosine kinase inhibitory action can be produced efficiently in a high yield at an industrial large scale by a convenient method

Preparation of 1-hydroxypyrazoles and 1-hydroxy-1,2,3-triazoles by dealkylation of pyrazole and triazole N-oxides

1-Hydroxypyrazoles were obtained from 2-benzylpyrazole 1-oxides by debenzylation with iodotrimethylsilane. 1-Hydroxy-1,2,3-triazoles were achieved from 2-benzyltriazole 1-oxides by debenzylation effected with conc. hydrobromic acid or from 2- or 3-p-methoxybenzyltriazole 1-oxides by de-p methoxybenzylation accomplished by treatment with conc. sulfuric acid. 1-Methoxy-1,2,3-triazole was obtained by de-p-methoxybenzylation of 1-methoxy-3-p-methoxybenzyl-1,2,3-triazolium tetrafluoroborate accomplished by treatment with conc. sulfuric acid. 1-Hydroxypyrazole was selectively N-benzylated in absence of base to give 2-benzylpyrazole 1-oxide which, upon selective substitution at the 3-position and subsequent debenzylation, produced 3-substituted 1-hydroxypyrazole. Acta Chemika Scandinavica 1996.

Alkylation, Acylation and Silylation of Azoles

Performing alkylation, acylation and silylation reactions in separate deprotonation and nucleophilic displacement steps allows for better control of reaction conditions and facilitates problem handling in these processes.In the alkylation of azoles the alkylating agents and solvents possess individual reaction capabilities which seem to be approximately additive.Monoalkylation occurs if the sum of the normalized reaction potentials is equal or larger than the pKa value of the azole.Dialkylation is avoided by keeping the sum of the normalized reaction potentials below the pKa value of the alkylazole.The applicability of these principles is demonstrated by the development of effective procedures for the methylation, benzylation, acetylation, methoxycarbonylation and trimethylsilylation of azoles.

2-Alkyl-1,2,3-Triazole-1-Oxides: Preparation and Use in the Synthesis of 2-Alkyltriazoles

Methylhydrazone oximes were obtaines by reaction of glyoxal, methylglyoxal, or diacetyl with methylhydrazine and hydroxylamine or from nitrosoacetone and methylhydrazine.The methylhydrazono oximes cyclize upon oxidation to 2-methyltriazole-N-oxides.Benzyl