2976-06-9

Usage

Chemical structure

1H-Pyrazole, 3-(2-furanyl)-5-phenyl-

Type of compound

Heterocyclic compound

Substituents

Furanyl group at the 3-position, phenyl group at the 5-position

Synthesis methods

Various methods available

Uses

Organic synthesis and pharmaceutical research

Potential biological activities

Yes

Applications in medicinal chemistry

Development of new drugs and pharmaceutical agents

Unique structure and properties

Interesting target for research and exploration in organic and medicinal chemistry.

Upstream product

• 2975-99-7 2-furyl phenylethynyl ketone 
• 527-69-5 2-furancarbonyl chloride 
• 536-74-3 phenylacetylene 
• 100-52-7 benzaldehyde 
• 699-18-3 2-(2-nitrovinyl)furan 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 98-01-1 furfural 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 18708-18-4 furfural tosylhydrazone 
• 1340547-66-1 C₁₅H₁₄O₂S 
• 5910-23-6 1-furan-2-yl-3-phenyl-propane-1,3-dione 

Relevant academic research and scientific papers

Fast and Efficient Continuous Flow Method for the Synthesis of Ynones and Pyrazoles

In this study, we developed a convenient and efficient two-step method for the synthesis of ynones in a flow reactor, through the generation of lithium acetylide and its subsequent reactions with acid chlorides. Using this approach, we obtained the ynones in moderate to good yields at room temperature. Moreover, we transformed the ynones into pyrazole derivatives through coupling with hydrazines. This transition metal-free process, mild reaction conditions, and broad functional group tolerance are all attractive features in comparison with conventional bench-top methods.

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.).

A highly efficient heterogeneous palladium-catalyzed cascade three-component reaction of acid chlorides, terminal alkynes and hydrazines leading to pyrazoles

In the presence of 0.5 mol% of 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-Pd(OAc)2] and 1.0 mol% of CuI, acid chlorides were coupled with terminal alkynes in Et3N at 50 °C to give α,β-unsaturated ynones, which were converted in situ into pyrazoles by the cycloaddition of hydrazines at room temperature with acetonitrile as cosolvent. The cascade reactions generated a variety of pyrazole derivatives in moderate to good yields, and this heterogeneous palladium catalyst exhibited higher catalytic activity than PdCl2(PPh3)2 and could be recovered and reused for at least 10 consecutive trials without any decreases in activity.

Preparation of 3,5-disubstituted pyrazoles and isoxazoles from terminal alkynes, aldehydes, hydrazines, and hydroxylamine

The reaction of terminal alkynes with n-BuLi, and then with aldehydes, followed by the treatment with molecular iodine, and subsequently hydrazines or hydroxylamine provided the corresponding 3,5-disubstituted pyrazoles or isoxazoles in good yields with high regioselectivity, through the formations of propargyl secondary alkoxides and α-alkynyl ketones. The present reactions are one-pot preparation of 3,5-disubstituted pyrazoles from terminal alkynes, aldehydes, molecular iodine, and hydrazines, and 3,5-disubstituted isoxazoles from terminal alkynes, aldehydes, molecular iodine, and hydroxylamine.

DABCO-promoted synthesis of pyrazoles from tosylhydrazones and nitroalkenes

An efficient synthesis of pyrazoles from tosylhydrazones and nitroalkenes was developed. In comparison with the previously reported 1,3-dipolar cycloaddition reaction of diazo compounds with electron-deficient alkenes or alkynes, this methodology proceeded with a sequential Baylis-Hillman/ intramolecular cyclization mechanism and a variety of reversed regioselectivity products were prepared in good yields.

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.

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.

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.

Regioselective synthesis of multisubstituted pyrazoles via cyclocondensation of β-thioalkyl-α,β-unsaturated ketones with hydrazines

Multisubstituted pyrazoles were efficiently synthesized by cyclocondensation of β-thioalkyl-α,β-unsaturated ketones with hydrazines under relatively mild conditions. A one-pot synthetic protocol through tandem Liebeskind-Srogl cross-coupling/cyclocondensation using a-oxo ketene dithioacetals as the starting materials was also realized for the same purpose.