767288-71-1

Upstream product

• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 107506-17-2 N-(2-(1-(hydroxyimino)ethyl)phenyl)-4-methylbenzenesulfonamide 
• 2142-69-0 2-bromophenyl methyl ketone 
• 49851-55-0 2,2'-dibromoacetophenone 
• 2142-70-3 2-iodoacetophenone 
• 113258-84-7 2-bromo-1-(2-iodophenyl)ethanone 
• 75230-56-7 N’-(1-(2-bromophenyl)ethylidene)-4-methylbenzene sulfonohydrazide 
• 768-60-5 4-methoxyphenylacetylen 
• 1597443-35-0 C₁₅H₁₆N₂O₃S 
• 1859-70-7 N-(2-acetylphenyl)-4-methylbenzenesulfonamide 
• 98-86-2 acetophenone 
• 941-55-9 4-toluenesulfonyl azide 
• 98-59-9 p-toluenesulfonyl chloride 
• 767288-67-5 (E)-N’-(1-(2-bromophenyl)ethylidene)-4-methylbenzenesulfonohydrazide 

Downstream Products

• 50407-18-6 2,3-Dimethylindazol 
• 34879-84-0 1,3-dimethyl-1H-indazole 
• 861803-79-4 1-ethyl-3-methyl-1H-indazole 

Relevant academic research and scientific papers

Copper-Catalyzed Isomerization and Cyclization of E/Z-o-Haloaryl N-Sulfonylhydrazones: Convenient Access to 1H-Indazoles

The isomerization of the C=N double bond in hydrazones has drawn considerable attention because of its potential for application in a broad range of chemical transformations. Generally, this isomerization can be realized either photochemically or thermall

Synthesis of benzofulvenes through chemoselective Sonogashira and Barluenga couplings of ortho ethynyl-N-tosylhydrazones and cycloisomerization

Chemoselective synthesis of ortho ethynylhydrazones 7 derived from 2-iodoacetophenone via a Sonogashira coupling is reported for the first time. In this challenging transformation, a site-selective coupling in the presence of a hydrazone function was developed. These compounds represent useful intermediates for the synthesis of benzofulvenes through a sequence of palladium-catalyzed cross-coupling and palladium-catalyzed 5-exo-dig cyclization.

Construction of 1H-indazoles from ortho-aminobenzoximes by the Mitsunobu reaction

Recently, there has been an upsurge in the occurrence of the indazole motif in drug discovery. Accordingly, newer, milder and more efficient routes towards their synthesis have emerged in the literature. We recently reported the Mitsunobu-triggered cyclod

Preparation method of indazole and application of indazole in medicine synthesis

The invention belongs to the field of chemicals, and relates to a preparation method of indazole and an application of the indazole in medicine synthesis. The invention discloses a preparation method of indazole and an application of the indazole in synthesizing 1H-indazole-3-carboxylic acid, lonidamine, a compound 8, a compound 9, a compound 10, axitinib, YD-3, YC-1 and similar substances thereof.

Copper(I) Oxide-Mediated Cyclization of o-Haloaryl N-Tosylhydrazones: Efficient Synthesis of Indazoles

An efficient synthesis of indazoles from readily accessible E/Z mixtures of o-haloaryl N-tosylhydrazones has been developed. The thermo-induced isomerization of N-tosylhydrazones is discussed. A series of valuable indazole derivatives are prepared in good yields, and the method has been successfully applied to the synthesis of the bioactive compounds, lonidamine, AF-2785, axitinib, YC-1 and YD-3.

Base-catalyzed synthesis of substituted indazoles under mild, transition-metal-free conditions

Back to basics: A transition-metal-free method developed for the synthesis of indazoles involves an inexpensive catalytic system composed of a diamine and K2CO3. Various (Z)-2-bromoacetophenone tosylhydrazones were converted into indazoles at room temperature in excellent yields (see example; Ts=p-toluenesulfonyl). The yield was improved by photoisomerization with UV light when E/Z isomeric mixtures of the starting material were used. Copyright

Ruthenium-catalyzed direct C-H amidation of arenes including weakly coordinating aromatic ketones

C-H activation: The ruthenium-catalyzed direct sp2 C-H amidation of arenes by using sulfonyl azides as the amino source is presented (see scheme). A wide range of substrates were readily amidated including arenes bearing weakly coordinating groups. Synthetic utility of the thus obtained products was demonstrated in the preparation of biologically active heterocycles. Copyright

Z-Selective synthesis of o-bromoacetophenone N-tosylhydrazones and formation of 3-methylindazoles in aqueous ethanol

A practical and effective Z-selective synthesis of o-bromoacetophenone N-tosylhydrazones is developed. Subsequent cyclization of Z-tosylhydrazones to furnish 3-methylindazoles is accomplished with the aid of copper and DMEDA in aqueous ethanol. Cyclization reactions are complete at ambient temperature in 10 min to afford the desired compounds in excellent yields.

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.

A practical, metal-free synthesis of 1H-Lndazoles

The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0-23 °C and is amenable to scale-up. The synthesis of 1 H-indazoles under these conditions is extremely mild compared with previous synthetic approaches and affords the desired compounds in good to excellent yields.