1575-29-7

Usage

Compound class

Indazole

Core structure

1H-indazole

Substitution

Methyl group at the 3-position and phenyl group at the 1-position

Usage

Synthesis of pharmaceuticals and research chemicals

Pharmacological activities

Anti-inflammatory, antitumor, and antiviral properties

Potential use

Treatment of various medical conditions

Subject of interest

Medicinal chemistry and pharmaceutical research

Upstream product

• 128364-60-3 [1-(2-Bromo-phenyl)-1-methoxy-ethyl]-phenyl-diazene 
• 1011736-72-3 N-[1-(2-Bromo-phenyl)-eth-(Z)-ylidene]-N'-phenyl-hydrazine 
• 1246849-39-7 (E)-1-(2-(phenylamino)phenyl)ethanone oxime 
• 551-93-9 2-aminoacetophenone 
• 23699-74-3 1-(2-anilinophenyl)ethan-1-one 
• 209412-48-6 1-(2-anilinophenyl)ethan-1-one oxime 
• 2142-69-0 2-bromophenyl methyl ketone 
• 59-88-1 phenylhydrazine hydrochloride 
• 583-11-9 N-(1-phenylethylidene)phenylhydrazine 
• 532-96-7 N-benzoyl-N'-phenylhydrazine 
• 100-63-0 phenylhydrazine 
• 2142-70-3 2-iodoacetophenone 
• 445-27-2 2'-Fluoroacetophenone 
• 201230-82-2 carbon monoxide 

Relevant academic research and scientific papers

Efficient synthesis of 1-aryl-1H-indazole derivatives via copper(I)-catalyzed intramolecular amination reaction

A copper(I)-catalyzed intramolecular amination reaction using CuI, KOH, and 1,4-dioxane at 105°C for the preparation of 1-aryl-1H-indazole derivatives was described. The method was applied to a wide scope of substrates and afforded indazole products in hi

Syntheses of 1-aryl-5-nitro-1h-indazoles and a general one-pot route to 1-aryl-1h-indazoles

An efficient route to substituted 1-aryl-1H-indazoles has been developed and optimized. The method involved the preparation of arylhydrazones from acetophenone or benzaldehyde substituted by fluorine at C2 and nitro at C5, followed by deprotonation and nucleophilic aromatic substitution (SNAr) ring closure in 45–90%. Modification of this procedure to a one-pot domino process was successful in the acetophenone series (73–96%), while the benzaldehyde series (63–73%) required a step-wise addition of reagents. A general one-pot protocol for 1-aryl-1H-indazole formation without the limiting substitution patterns required for the SNAr cyclization has also been achieved in 62–78% yields. A selection of 1-aryl-1H-indazoles was prepared in high yield by a procedure that requires only a single laboratory operation.

Divergent strategy for the chemoselective synthesis of N-Arylbenzimidazoles and N-Arylindazoles from arylamino oximes

An efficient and divergent synthesis of N-arylbenzimidazoles and N-arylindazoles from arylamino oximes based on reaction conditions selection was developed. The synthesis was approached by treating oximes with BTC and the chemoselectivity was regulated by the amount of Et3N. This switchable N–N and N–C bond formation process features mild reaction conditions, simple execution, high chemoselectivity and broad substrate scope.

DAST-promoted Beckmann rearrangement/intramolecular cyclization of acyclic ketoximes: Access to 2-oxazolines, benzimidazoles and benzoxazoles

The first example of DAST-promoted Beckmann rearrangement/intramolecular cyclization of acyclic ketoximes is described. This unique protocol represents a direct and effective pathway to 2-oxazolines, benzimidazoles and benzoxazoles in moderate to good yields.

Facile access to 1H-indazoles through iodobenzene-catalyzed C-H amination under mild, transition-metal-free conditions

The transition-metal- and halogen-free synthesis of N-aryl-substituted 1H-indazole and derivatives was accomplished on the basis of the iodobenzene-catalyzed intramolecular C-H amination of hydrazones under mild conditions. Reactions of hydrazones derived

Copper powder-catalyzed C-N bond formation of arylhydrazones of 2-bromobenzaldehydes leading to 1-aryl-1 H-indazoles

Arylhydrazones of 2-bromobenzaldehydes and its analogs are cyclized in PEG-400 at 110C in the presence of a catalytic amount of copper powder along with NaOtBu to give 1-aryl-1H-indazole derivatives in good yields.

Assembly of N, N -disubstituted hydrazines and 1-aryl-1 H-indazoles via copper-catalyzed coupling reactions

CuI-catalyzed coupling of N-acyl-N′-substituted hydrazines with aryl iodides takes place at 60-90 °C to afford N-acyl-N′,N′- disubstituted hydrazines regioselectively and thereby gives a facile method for assembling N,N-diaryl hydrazines. N-Acyl-N′-substituted hydrazines can also react with 2-bromoarylcarbonylic compounds at 60-125 °C under the catalysis of CuI/4-hydroxy-l-proline to provide 1-aryl-1H-indazoles.

Synthesis of 1-aryl-1H-indazoles via a ligand-free copper-catalyzed intramolecular amination reaction

A general synthesis of 1-aryl-1-H-indazoles from o-halogenated aryl aldehydes or ketones and aryl hydrazines was described. This protocol included an intermolecular condensation and a ligand-free copper-catalyzed intramolecular Ullmann-type coupling react

Copper-catalyzed N-arylation of amines with part-per-million catalyst loadings under air at room temperature

An efficient copper-catalyzed method for N-arylation of amines has been developed with part-per-million catalyst loadings at room temperature under air. Reactions of substituted (E)-1-(2-halophenyl)alkanone oximes with aliphatic amines or aromatic amines

METHOD OF SYNTHESIZING 1H-INDAZOLE COMPOUNDS

A method is provided for synthesizing 1H-indazole compounds in which aromatic carbonyl compounds are reacted with a nitrogen source to form oximes which are then converted to 1H-indazoles.