Synthesis and Crystal Structure of 4-(1,3-Diphenyl-1H-pyrazol-5-yl)pyridine

Prasad, T. N. Mahadeva; Raghava, B.; Sridhar, M. A.; Rangappa, Kanchugarakoppal S.; Prasad, J. Shashidhara

doi:10.2116/xraystruct.26.75

Cited by 3 publications

(1 citation statement)

References 8 publications

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“…1.272(2) vs 1.348(3) Å; ∑ r cov (NN) = 1.20 Å, ∑ r cov (N–N) = 1.42 Å; 1.247(3) Å in Ph–NN–Ph) . The central five-membered pyrazole ring is planar (deviation from planarity less than 2°), with bond lengths and angles in the expected ranges …”

Section: Resultsmentioning

confidence: 90%

Catalytic Trimerization of Bis-silylated Diazomethane

Ibad¹,

Langer

Reiß³

et al. 2012

J. Am. Chem. Soc.

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(Me(3)Si)(2)CNN isomerizes upon addition of traces of [Me(3)Si](+) ions to give (Me(3)Si)(2)NNC, which then undergoes an unusual trimerization reaction to give exclusively 4-diazenyl-3-hydrazinylpyrazole. As catalyst the isonitrilium ion, [(Me(3)Si)(2)NNC(SiMe(3))](+), was identified and fully characterized. Experiments and computations indicate a three-step reaction including isomerization of diazomethane, a C-C or N-C coupling, and a formal cycloaddition reaction. The kinetics and thermodynamics are discussed on the basis of DFT calculations.

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Section: Resultsmentioning

confidence: 90%

Catalytic Trimerization of Bis-silylated Diazomethane

Ibad¹,

Langer

Reiß³

et al. 2012

J. Am. Chem. Soc.

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Synthesis and characterization of 1‐phenyl‐3‐(propan‐2‐yl)‐1H‐pyrazol‐5‐ol single crystals

Vyas

Akbari

Tala

et al. 2012

Cryst. Res. Technol.

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The synthesis of pyrazoles and its derivatives remains of great interest due to their wide applications in pharmaceutical and agrochemical industry. The 1‐phenyl‐3‐(propan‐2‐yl)‐1H‐pyrazol‐5‐ol was synthesized. The 1‐phenyl‐3‐(propan‐2‐yl)‐1H‐pyrazol‐5‐ol single crystals were grown by slow solvent evaporation technique using mixture of chloroform and methanol as a solvent. Yellowish and transparent crystals having maximum dimensions of 0.005 m × 0.004 m × 0.002 m were grown. The crystals were characterized by powder XRD, FT–IR, TG–DTA–DSC and dielectric study. The crystals remained stable up to 160 °C and then start decomposing. The DSC suggested both endothermic and exothermic reactions. One broad exothermic peak was observed at 558.1 °C due to complete decomposition of the sample into the gaseous phase and reaction within the products. Thermodynamic and Kinetic parameters of decomposition were calculated by Coats–Redfern formula. The dielectric study was carried out in the frequency range from 50 Hz to 5 MHz at room temperature. The dielectric constant decreased as the frequency of the applied field increased. The variations of dielectric loss, a.c. conductivity and a.c. resistivity also studied with the frequency of the applied field. Jonscher's power law was verified for a.c. conductivity.

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Synthesis and Crystal Structure of 3-(3-Methylthiophen-2-yl)-1,5-diphenyl-1<i>H</i>-pyrazole

Raghava

Prasad

Lakshminarayana³

et al. 2012

X-ray Structure Analysis Online

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A solution of respective (Z)-3-(methylthio)-1-(3-methylthiophen-2-yl)-3-phenylprop-2-en-1-one (5 mmol, 1 eq) was added to a suspension of phenylhydrazine (7.5 mmol, 1.5 eq) and t-BuOK (7.5 mmol, 1.5 eq) in t-BuOH (25 ml) at room temperature. The reaction mixture was refluxed with constant stirring for 8 -10 h (monitored by TLC). The title compound, C20H16N2S, was synthesized, and the structure was investigated by X-ray crystallography and characterised by NMR and IR spectroscopy. The compound crystallizes in the orthorhombic crystal class in the space group F2dd with cell parameters a = 6.1830(5)Å, b = 27.797(5)Å, c = 38.234 (7) and Z = 16. Pyrazole refers both to the class of simple aromatic ring organic compounds of the heterocyclic diazole series, characterized by a 5-membered ring structure composed of three carbon atoms and two nitrogen atoms in adjacent positions, and to the unsubstituted parent compound. Being so composed and having pharmacological effects on humans, they are classified as alkaloids, although they are rare in nature. The pyrazole ring is widely found as the core structure in a large variety of compounds that possess important agrochemical and pharmaceutical activities. 1,2 Pyrazole derivatives are well known for analgesic, and antidiabetic activities. [3][4][5] Numerous compounds containing the pyrazole moiety exhibit a wide range of biological activities, such as anti-inflammatory, 6 antimicrobial, 7 and antiviral 8 properities. In this context, and as a part of our ongoing research on pyrazoles and their crystal structures, herein we report on the synthesis and crystal structure of the title compound.

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Synthesis and Crystal Structure of 4-(1,3-Diphenyl-1H-pyrazol-5-yl)pyridine

Cited by 3 publications

References 8 publications

Catalytic Trimerization of Bis-silylated Diazomethane

Catalytic Trimerization of Bis-silylated Diazomethane

Synthesis and characterization of 1‐phenyl‐3‐(propan‐2‐yl)‐1H‐pyrazol‐5‐ol single crystals

Synthesis and Crystal Structure of 3-(3-Methylthiophen-2-yl)-1,5-diphenyl-1<i>H</i>-pyrazole

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