81945-59-7

Usage

Chemical composition

Consists of a cyclohexyl group and a 1,2,3-triazole ring.

Use in organic synthesis

Serves as a building block for the construction of various bioactive molecules and pharmaceuticals.

Ability to bind to metal ions

The 1,2,3-triazole ring can bind to metal ions, making it useful in coordination chemistry and metal-catalyzed reactions.

Antifungal and antimicrobial properties

Exhibits potential antifungal and antimicrobial properties, making it a promising candidate for the development of new drugs.

Use as a ligand

Has been used as a ligand in the development of catalysts for organic reactions.

Use as an inhibitor

Has been used as an inhibitor in the study of enzyme function.

Potential applications

Has a wide range of potential applications in medicinal chemistry, organic synthesis, and chemical biology.

Upstream product

• 108-91-8 cyclohexylamine 
• 108-05-4 vinyl acetate 
• 19573-22-9 cyclohexyl azide 

Relevant academic research and scientific papers

An azide and acetylene free synthesis of 1-substituted 1,2,3-triazoles

This paper details a simple and efficient 3-component synthesis of 1-substituted 1,2,3-triazoles using a primary amine, 2,2-dimethoxyacetaldehyde and tosylhydrazide. The reaction proceeds in good to excellent yields using either aliphatic or aromatic amine substrates and is tolerant of a wide range of functional groups including electron-rich and deficient aryl groups, terminal alkynes, ketones and highly sterically encumbered amines.

[4 + 1] Annulation of in situ generated azoalkenes with amines: A powerful approach to access 1-substituted 1,2,3-triazoles

1-Substituted 1,2,3-triazoles represents ‘privileged’ structural scaffolds of many clinical pharmaceuticals. However, the traditional methods for their preparation mainly rely on thermal [3 + 2] cycloaddition of potentially dangerous acetylene and azides. Here we report a base-mediated [4 + 1] annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones (DFHZ-Ts) with amines under relatively mild conditions. This azide- and acetylene-free strategy provides facile access to diverse 1-substituted 1,2,3-triazole derivatives in high yield in a regiospecific manner. This transformation has great functional group tolerance and can suit a broad substrate scope. Furthermore, the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality, practicability and applicability.

Microwave irradiation as an effective means of synthesizing uninfstituted N-linked 1,2,3-triazoles from vinyl acetate and azides

N-Linked 1,2,3-triazoles have been prepared by a reaction of azides with vinyl acetate under microwave irradiation. Additionally, a microwave-assisted, two-step, one-pot procedure from halides involving azideinfstitution in diethyl ether, followed by -reaction with vinyl acetate, has effectively been employed. Georg Thieme Verlag Stuttgart - New York.