50603-96-8

Usage

Chemical structure

pyrazole derivative with a bromine-substituted phenyl ring at the 3-position and a phenyl ring at the 5-position

Biological activities

anti-inflammatory, analgesic, antipyretic

Potential applications

treating inflammatory and pain-related conditions, antimicrobial agent, anticancer agent

Ongoing research

synthesis, properties, potential applications in medicinal chemistry

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 536-74-3 phenylacetylene 
• 142739-40-0 1-(4-bromo-phenyl)-3-phenyl-prop-2-yn-1-ol 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 19350-68-6 p-bromobenzaldehyde tosylhydrazone 
• 1774-66-9 3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 23565-63-1 1-(4-bromophenyl)-3-phenylpropynone 
• 586-75-4 4-chlorobenzoyl chloride 

Relevant academic research and scientific papers

One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization

Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone-amine cyclization under PTC conditions was described. The results of controlled experiments support the operation of two sequential catalytic cycles (ASC/cyclization) and achievement of complementary/opposite regioselectivity via ynone-bound palladium in a one-pot approach. Moreover, the in situ PdNPs recovered after the first catalytic cycle of the one-pot reaction sequence have been reused again five times successively. Besides, prior to the above studies, the efficacy of some common Pd-N-heterocyclic carbene (Pd-NHC) complexes in catalyzing the same one-pot two-step reaction sequence (Cu-free ASC/cyclization) both in water and organic solvents was also optimized. In situ generation of PdNPs from above Pd-NHCs in water was also identified, but they are not reusable due to their large size distribution.

Sunlight-promoted Direct Irradiation of N-centred Anion: The Photocatalyst-free Synthesis of Pyrazoles in Water

A practical method through sunlight mediated annulation of α,β-unsaturated hydrazones has been developed for the synthesis of pyrazole. Based on the analysis of UV-Vis absorption of the substrate, the reaction was designed to avoid the use of external photocatalysis and proceeds via direct irradiation of N-centred anion by sunlight. The key features of this reaction include operational simplicity, readily available reagents, and amenability to gram-scale synthesis. (Figure presented.).

Transition Metal, Azide, and Oxidant-Free Homo- and Heterocoupling of Ambiphilic Tosylhydrazones to the Regioselective Triazoles and Pyrazoles

With N-tosylhydrazone as an ambiphilic reagent, an unprecedented cyclization reaction of two identical or different tosylhydrazones has been developed to access various 4,5-disubstituted-2H-triazoles under transition metal, azide, and oxidant-free conditi

A facile and expeditious approach to substituted 1H-pyrazoles catalyzed by iodine

A facile and expeditious method for the synthesis of 1H-pyrazoles by the reaction of α,β-unsaturated aldehydes/ketones and sulfonyl hydrazide catalyzed by as low as 2 mol % I2 has been demonstrated. This synthetic system features simple operation and mild reaction conditions, and displays a broad functional group tolerance furnishing good to excellent yields.

Synthesis of 3,5-disubstituted-1H-pyrazoles from acid chlorides, alkynes, and hydrazine in the presence of silica-supported-zinc bromide

An efficient one-pot palladium- And copper-free procedure has been developed for a convenient synthesis of 3,5-disubstituted-1H-pyrazoles from various acid chlorides, terminal alkynes and hydrazine by a coupling reaction and cyclocondensation sequence. Acid chlorides react with terminal alkynes in the presence of silica-supported-zinc bromide to give α,β-unsaturated ynones, and in situ conversion into pyrazoles by the hydrazine cyclocondensation.

Synthesis of pyrazoles through copper-catalyzed three-component coupling of aldehydes, alkynes, and p-toluenesulfonylhydrazide

A convenient one-pot synthesis of 3,5-disubstitued 1H-pyrazoles through copper-catalyzed three-component coupling of aldehydes, alkynes, and p-toluenesulfonylhydrazide has been developed. This method provides a flexible and rapid route to 3,5-disubstituted 1H-pyrazoles.

Facile one-pot synthesis of 3,5-disubstituted 1 h -pyrazoles from propargylic alcohols via propargyl hydrazides

A new and efficient metal-free, two-component, one-pot approach to a variety of 3,5-disubstituted 1H-pyrazoles has been developed from propargylic alcohols. This transformation proceeds via an acid-catalyzed propargylation of N,N-diprotected hydrazines followed by base-mediated 5-endo-dig cyclization leading to 3,5-disubstituted 1H-pyrazoles in good overall yields. Georg Thieme Verlag Stuttgart. New York.

Chemoselective synthesis of substituted pyrazoles through AgOTf-catalyzed cascade propargylic substitution-cyclization-aromatization

A cascade AgOTf-catalyzed chemoselective approach to 3,5/1,3-disubstitued pyrazoles from propargylic alcohols and para-tolylsulfonohydrazide has been developed. Good chemoselectivity is observed depending on the different substituents in the alkyne moiety of the propargylic alcohols, generating two different kinds of products through different aromatization mechanisms. The pyrazolo[5,1-a]isoquinoline skeleton can also be effectively constructed by this method through a cascade bicyclization process.

An efficient one-pot synthesis of 3,5-disubstituted 1H-pyrazoles

An efficient, general, one-pot, three-component procedure for the preparation of 3,5-disubstituted 1H-pyrazoles via condensation of substituted aromatic aldehydes, tosylhydrazine and terminal alkynes in toluene is reported. The reaction tolerates a variety of functional groups and sterically hindered substrates to afford the desired pyrazoles in yields of 67-91%.

A complementary approach to 3,5-substituted pyrazoles with tosylhydrazones and terminal alkynes mediated by TfOH

A complementary method for the preparation of 3,5-substituted pyrazoles in moderate to high yields has been explored via TfOH-induced addition of tosylhydrazones to the terminal alkynes. This acid-induced addition procedure might be an operationally safe alternative compared to typical 1,3-dipolar cycloaddition as there is no involvement of diazo compounds.