16151-06-7

Upstream product

• 20442-65-3 1-(4-methylphenyl)-3-phenylprop-2-yn-1-one 
• 100-63-0 phenylhydrazine 
• 15206-66-3 1,3-diphenyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazole 
• 125748-42-7 (5R,9S)-2,6,8-Triphenyl-9-p-tolyl-3-oxa-1,7,8-triaza-spiro[4.4]nona-1,6-dien-4-one 
• 129193-16-4 (4S,5R)-4-Benzoylamino-1,3-diphenyl-5-p-tolyl-4,5-dihydro-1H-pyrazole-4-carboxylic acid 
• 15206-66-3 C₂₂H₂₀N₂⁽¹⁺⁾ 
• 624-31-7 4-tolyl iodide 
• 536-74-3 phenylacetylene 
• 127876-36-2 2-(benzotriazol-1-yl)acetophenone 
• 104-87-0 4-methyl-benzaldehyde 
• 371772-51-9 (Z)-2-(benzotriazol-1-yl)-3-(4-methylphenyl)-1-phenyl-2-propen-1-one 
• 57427-79-9 (Z)-4-(4-methylbenzylidene)-2-phenyloxazol-5(4H)-one 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 27729-96-0 1-phenyl-3-(p-methylphenyl)-2,3-epoxy-1-propanone 

Relevant academic research and scientific papers

Molecular iodine: A green and inclusive catalyst for the synthesis of highly functionalized 1,3,5-trisubstituted pyrazoles in aqueous medium

A library of 1,3,5-trisubstituted pyrazoles was synthesized in excellent yields from the reaction of aldehyde, phenylhydrazine and alkynes in the presence of iodine via an eco-friendly, simple process performed in aqueous medium. This single pot transformation generates new CN, C-C, C-N bonds and proceeds by a domino reaction involving the formation of Schiff base, Mannich addition and finally intramolecular cyclisation. The Royal Society of Chemistry 2014.

Cycloaddition of Nitrile Imines with Enamides: An Approach to Functionalized Pyrazolines and Pyrazoles

An efficient [3 + 2] cycloaddition of in situ generated nitrile imines with enamides has been established. A wide range of functionalized pyrazoline derivatives (53 examples) were obtained in moderate to good yields (up to 96%) under very mild conditions. This protocol features broad substrate scope, good functional group tolerance, and operational simplicity. Practical transformation of the products into useful pyrazoles via a one-pot process and the scalability of this protocol highlight the utility of this synthetic methodology.

Visible light mediated metal-free oxidative aromatization of 1,3,5-trisubstituted pyrazolines

The visible light mediated oxidation of 1,3,5-trisubstituted pyrazolines under metal-free conditions was developed. Various substituted pyrazolines were oxidized to pyrazoles by irradiation with visible light/sunlight. A plausible mechanism was proposed f

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.

13C NMR spectroscopy of heterocycles: 1-phenyl-3-aryl/t-butyl-5-arylpyrazoles

A series of chalcones 1-12 were converted to pyrazolines (1Pi-12Pi) by reaction with phenylhydrazine followed by DDQ oxidation to produce the corresponding pyrazoles (1Pz-12Pz). Three 1-phenyl-3-t-butyl-5-arylpyrazoles (13Pz-15Pz) were synthesized using an analogous approach. Molecular modeling studies predicted the 5-aryl group of the pyrazoles for both series to have a torsion angle of 52°-54° whereas the 1-phenyl group was predicted to have 35°-37° torsion angles. The 3-aryl group was predicted to be essentially coplanar (-3°) with the pyrazole system in the first series. 13C NMR data for both series, 1Pz-12Pz and 13Pz-15Pz, were collected in DMSO-d6 at 50°C. A plot of the C4 chemical shifts for 1Pz-12Pz versus Hammet constants for 5-aryl substituents yielded a very good linear correlation (R2=0.96) with a slope of 1.5. The chemical shift data for C4 showed little or no dependence on 3-aryl substituents. The result for 13Pz-15Pz, despite only three points, was consistent with the first series results and yielded a ρ value of 2.0. Distal transmission of substituent effects (5-aryl groups) to C4 of the pyrazole system was reduced by roughly 50-60% of that of the analogous planar isoxazole system, but are not consistent with results for the similarly twisted 4-bromoisoxazoles.

Visible light catalyzed aromatization of 1,3,5-triaryl-2-pyrazolines by platinum(II) polypyridyl complex under oxidant-free condition

With visible light (λ=450 nm) irradiation of a catalytic amount of platinum(II) terpyridyl complex, 1,3,5-triaryl-2-pyrazolines can be smoothly converted to their corresponding pyrazoles and hydrogen in quantitative yields with no use of any oxidant at ro

Br?nsted acid-mediated annulations of 1-cyanocyclopropane-1-carboxylates with arylhydrazines: Efficient strategy for the synthesis of 1,3,5-trisubstituted pyrazoles

1-Cyanocyclopropane-1-carboxylates are reacted with arylhydrazines to afford 1,3,5-trisubstituted pyrazoles under the influence of a Br?nsted acid. Formally, this transformation can be regarded as an annulation of three-membered rings with α-carbonyl and

Radical Addition of Hydrazones by α-Bromo Ketones to Prepare 1,3,5-Trisubstituted Pyrazoles via Visible Light Catalysis

A novel efficient tandem reaction of hydrazones and α-bromo ketones is reported for the preparation of 1,3,5-trisubstituted pyrazoles by visible light catalysis. In this system, the monosubstituted hydrazones show wonderful reaction activity with alkyl radicals, generated from α-bromo ketones. A radical addition followed by intramolecular cyclization affords the important pyrazole skeleton in good to excellent yields. This efficient strategy under mild conditions with wide group tolerance provides a potential approach to the 1,3,5-trisubstituted pyrazoles.

Synthesis and anticancer activity of 1,3,5-triaryl-1H-pyrazole

Previous studies demonstrated that some pyrazole derivatives could be considered as potential anticancer agents. A series of 1,3,5-triaryl-1H-pyrazole derivatives were prepared by the reaction of phenylhydrazin and different chalcones. The previous classi

3,4-Dihydro-2H-pyran promoted aerobic oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines

An unprecedented facile oxidation of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines (DHPs) to the corresponding pyrazoles and pyridines was observed, mediated by 3,4-dihydro-2H-pyran in air. The reaction showed excellent reactivity, functional group tolerance, and high yield without using any metal and/or halogen based oxidizing agents.