1967-99-3

Usage

Uses

Used in Pharmaceutical Industry:
3-methyl-4,5,6,7-tetrahydro-2H-indazole is used as a building block for the synthesis of various pharmaceutical compounds due to its unique chemical structure and potential biological activities. Its role in the development of new drugs is significant, as it can be incorporated into molecules with therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, 3-methyl-4,5,6,7-tetrahydro-2H-indazole is utilized as a key component in the creation of agrochemical compounds. Its incorporation into these products can enhance their effectiveness in various agricultural applications.
Used as an Anxiolytic Agent:
3-methyl-4,5,6,7-tetrahydro-2H-indazole is studied for its potential as an anxiolytic agent, making it a candidate for the treatment of anxiety disorders. Its anxiolytic properties can contribute to the development of new therapeutic approaches for managing anxiety-related conditions.
Used in Central Nervous System Stimulation:
3-methyl-4,5,6,7-tetrahydro-2H-indazole has been investigated for its potential as a central nervous system stimulant. This application could lead to the development of medications that enhance cognitive function or address certain neurological disorders.
Used in Cannabinoid Receptor Activity:
3-methyl-4,5,6,7-tetrahydro-2H-indazole has shown activity in the cannabinoid receptors, which suggests its potential use in the development of drugs targeting these receptors for various therapeutic purposes, including pain management and neuroprotection.

Upstream product

• 2214-01-9 3-methyl-3a,4,5,6,7,7a-hexahydro-1H-indazole 
• 874-23-7 2-acetylcyclohexanone 
• 75624-86-1 Triphenyl(4,5,6,7-tetrahydro-3-methyl-1H-indazol-7-yl)phosphonium-bromid 
• 75624-66-7 1-<2-Methoxy-3-(triphenylphosphoranyliden)-1-cyclohexen-1-yl>ethanon 
• 75624-74-7 (3-Acetyl-2-oxocyclohexyl)triphenylphosphonium-chlorid 
• 74581-96-7 (2-Methoxy-1-cyclohexen-1-yl)triphenylphosphonium-bromid 
• 931-49-7 1-ethenylcyclohexene 
• 932-66-1 1-cyclohexenyl methyl ketone 

Relevant academic research and scientific papers

Discovery of 3,3′-Spiro[Azetidine]-2-oxo-indoline Derivatives as Fusion Inhibitors for Treatment of RSV Infection

A new series of 3,3′-spirocyclic-2-oxo-indoline derivatives was synthesized and evaluated against respiratory syncytial virus (RSV) in a cell-based assay and animal model. Extensive structure-activity relationship study led to a lead compound 14h, which e

A modified and practical synthetic route to indazoles and pyrazoles using tungstate sulfuric acid

Tungstate sulfuric acid-catalyzed Knorr reaction have been used as a simple, rapid, atom economic and green method for the synthesis of indazole and pyrazole derivatives based on the condensation of hydrazine derivatives and ss-dicarbonyl compounds under solvent-free conditions. It was found that the catalyst could be recovered and reused without significant loss of its activity. The use of this method provides a novel and improved modification of Knorr synthesis in terms of clean reaction profile, use of a safe catalyst and solvent-free conditions. A green method for the synthesis of indazole and pyrazole derivatives from the condensation of hydrazine derivatives with dicarbonyl compounds has been described. Tungstate sulfuric acid (TSA) catalyzed efficiently the reactions to give good yields.

Gold-catalyzed hydroamination of alkynes and allenes with parent hydrazine

A diverse array of nitrogen-containing compounds were formed by the addition of hydrazine to alkynes, diynes, enynes, and allenes in the presence of cationic gold(I) complexes with a cyclic (alkyl)(amino)carbene ligand (see scheme; the X-ray crystal structure of the gold-hydrazine complex is shown). This hydroamination is an ideal initial step for the preparation of acyclic and heterocyclic bulk chemicals. Dipp=2,6-diisopropylphenyl. Copyright

Synthesis of hydrogenated indazole derivatives starting with α,β-unsaturated ketones and hydrazine derivatives

The reaction of hydrazine derivatives with α,β-unsaturated ketones, such as cyclohexenyl(phenyl)methanone and (E)-2-benzylidenecyclohexanone, were investigated. The reaction between methylhydrazine and e.g., cyclohexenyl(phenyl)methanone was particularly interesting as 3a,4,5,6,7,7a-hexahydro-1-methyl-3-phenyl-1H-indazole was obtained as the major product together with 4,5,6,7-tetrahydro-2-methyl-3-phenyl-2H-indazole as a minor product.

Transformations of 4,9-Dimethyl-2,3,7,8-tetra-azatetracyclo4,1206,10>trideca-1,6-diene , a Bishydrazone having Two Bridgehead Double Bonds

Reduction of the anti-Bredt bishydrazone 4,9-dimethyl-2,3,7,8-tetra-azatetracyclo4,1206,10>trideca-1,6-diene with lithium aluminium hydride-aluminium chloride or by catalytic hydrogenation gives the bishydrazine 1,6-dimethyl-2,3,7,8-tetra-azatetracyclo4,1206,10>tridecane, but reaction with either lithium aluminium hydride or aluminium chloride gives dihydropyrazoles by ring cleavage.

Reactions with Organophosphorus Compounds, XLVI. Reactivity Umpolung of 1,3-Dioxo Compounds through Introduction of a Triphenylphosphonio Group. - Regioselective Syntheses of Isoxazoles and Pyrazoles from (2,4-Dioxoalkyl)triphenylphosphonium Salts

Phosphonium salts 2 and 6, upon deprotonation with BuLi and subsequent reaction with acyl halides, yield the γ-acyl derivatives 3 and 7, respectively, which on treatment with hydrochloric acid afford the corresponding (dioxoalkyl)phosphonium salts 4 and 8.Isoxazole derivatives 9 and 10 are formed regioselectivly from 4 and 8 with NH2OH*HCl, while with R-NH-NH2*HCl (R = H or C6H5) the pyrazole-containing phosphonium salts 14 and 15 are obtained in an analogous reaction.In each case the direction of cyclisation is different to the reactions of the corresponding non-phosphorus substituted 1,3-dioxo compounds.On treatment with aqueous NaOH 9 and 10 are cleaved to triphenylphosphane oxide and isoxazoles 11 and 12, while 14 and 15 yield the pyrazoles 16 and 17.Wittig reaction of 9a or 14a with aldehydes or ketones leads to the isoxazole olefins 13 or the pyrazole olefins 18, respectively.