92234-54-3

Usage

Uses

Used in Pharmaceutical Industry:
1-(1-Adamantyl)pyrazole is used as a pharmaceutical compound for its anticonvulsant and neuroprotective effects, making it a candidate for the development of treatments for various neurological conditions and neurodegenerative diseases.
Used in Organic Synthesis:
1-(1-Adamantyl)pyrazole is used as a building block in organic synthesis, contributing to the creation of new and complex molecules with potential applications in various fields, including pharmaceuticals, materials science, and chemical research.
Used in Corrosion Inhibition:
1-(1-Adamantyl)pyrazole is used as a corrosion inhibitor, leveraging its unique properties to protect materials from degradation in various industrial applications, particularly in the manufacturing and maintenance of metal structures and equipment.

InChI:InChI=1/C13H18N2/c1-2-14-15(3-1)13-7-10-4-11(8-13)6-12(5-10)9-13/h1-3,10-12H,4-9H2

Upstream product

• 288-13-1 NH-pyrazole 
• 768-90-1 1-Adamantyl bromide 
• 141185-56-0 1,3-dehydroadamantane 
• 828-51-3 1-Adamantanecarboxylic acid 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 16782-39-1 adamant-1-ylhydrazine dihydrochloride 
• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 16782-38-0 1-adamantylhydrazine 

Downstream Products

• 768-95-6 1-adamanthanol 
• 92234-57-6 1-(1-adamantyl-3-ol)-4-nitropyrazole 

Relevant academic research and scientific papers

A General One-Pot Protocol for Hindered N-Alkyl Azaheterocycles from Tertiary Carboxylic Acids

In this letter, we report a general one-pot strategy that utilizes three elementary steps (decarboxylative hydrazination, Boc deprotection, and heterocycle condensation) to regioselectively prepare hindered C(sp3) substituted pyrazoles and triazoles. The operational simplicity of this sequence and ubiquity of tertiary carboxylic acids allow rapid access to hindered N-alkyl azaheterocycles that will be useful to practitioners of medicinal chemistry and agro-chemistry.

Electrochemical Decarboxylative N-Alkylation of Heterocycles

An operationally simple method to employ nonactivated carboxylic acids as alkylating agents in the N-alkylation of heterocycles is reported through an electrochemically driven anodic decarboxylative process. A wide substrate scope across a range of heterocycles is demonstrated along with a series of applications that significantly reduce the step count required to access such medicinally relevant structures.

Synthesis of azolyl-substituted adamantane derivatives and their coordination compounds

Reactions of adamantylazoles with nucleophiles (water, carbon monoxide, acetonitrile) in sulfuric acid were studied. New bifunctional adamantane derivatives containing one heterocyclic substituent and one hydroxyl or acetamide substituent were synthesized. The coordination compounds of copper(II) and zinc(II) with 1-adamantyl-1,2,4-triazole, 4-adamantylpyrazole, and 4-adamantyl-3,5-dimethylpyrazole were synthesized and structurally characterized. These complexes are first examples of coordination compounds of azolyladamantanes.

Regioselective adamantylation of N-unsubstituted pyrazole derivatives

Reaction of NH-pyrazoles with 1-bromoadamantane in a high pressure stainless steel autoclave (250 ml, maximum working pressure of 200 atm) gives regioselectively 1-adamantyl or 4-adamantylpyrazoles depending on the temperature.

ADAMANTYLATION OF N-UNSUBSTITUTED PYRAZOLE DERIVATIVES: MECHANISTIC AND STRUCTURAL STUDIES

Reaction of NH-pyrazoles with 1-bromoadamantane in a high pressure stainless steel autoclave gives regioselectively 1-(1-adamantyl)- or 4-(1-adamantyl)pyrazoles depending on the temperature.A series of cross-experiments allows to establish the mechanism of this reaction.The molecular structure of the most simple derivative, 4-(1-adamantyl) pyrazole (3a), has been determined.Intramolecular N-H...N hydrogen bonds hold the four independent molecules together in a helix system parallel to the c axis.The crystal is built up of two centrosymmetrically related helices.

SIMILARITY IN PHYSICAL ORGANIC CHEMISTRY: SUBSTITUENT EFFECTS ON THE INTRINSIC BASICITY OF 4-SUBSTITUTED PYRAZOLES

The gas-phase basicities of eight pyrazoles substituted only at position 4 (R4 = H, NO2, F, Cl, CO2C2H5, CH3, NH2, 1-adamantyl) were measured by Fourier transform ion cyclotron resonance.The experimental values were treated in two ways, first by comparing these values with the AM1-calculated proton affinities.Since the correlation was reasonably good , a set of 17 further 4-substituted pyrazoles and their cations were calculated using the AM1 approximation and their gas-phase basicities were estimated.Second, both the experimental and the AM1-calculated values were considered within the framework of the Taft-Topsom analysis of substituent effects.Comparison of the analyses for pyrazoles and pyridines led to the unexpected result that, in spite of differences in ring size and number of heteroatoms, both systems behave remarkably alike.

Synthesis and in vitro antiviral activity of some N-adamantylazoles and benzazoles

Some new N-adamantyl derivatives of five-membered and benzo fused five-membered π-excessive heteroaromatic compounds were synthesized and tested as antiviral agents against Semliki Forest Virus (SFV). The 2-(1-adamantyl)-1,2,3,4-tetrazole derivative was as active as and significantly less toxic than amantadine itself.