Reaction of arylhydrazines with an α-alkynyl-carbonylic compound: an unexpected hydration reaction

Aldeco‐Pérez, Eugenia; Álvarez-Toledano, Cecilio; Toscano, Rubén A.; García-Estrada, José Guadalupe; Penieres‐Carrillo, Jose Guillermo

doi:10.1016/j.tetlet.2008.03.022

Cited by 4 publications

(1 citation statement)

References 8 publications

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“…HRMS (ESI): calcd for C 16 H 14 N 2 Na 257.1055 [M + Na] + , found 257.1049. The spectral data were in agreement with those reported previously for this compound …”

Section: Methodssupporting

confidence: 92%

Synthesis of Pyrazoles via Electrophilic Cyclization

2011

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Electrophilic cyclizations of α,β-alkynic hydrazones by molecular iodine were investigated for the synthesis of 4-iodopyrazoles. α,β-Alkynic hydrazones were readily prepared by the reactions of hydrazines with propargyl aldehydes and ketones. When treated with molecular iodine in the presence of sodium bicarbonate, α,β-alkynic hydrazones underwent electrophilic cyclization to afford 4-iodopyrazoles in good to high yields. Iodocyclization was general for a wide range of α,β-alkynic hydrazones and tolerated the presence of aliphatic, aromatic, heteroaromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.

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“…HRMS (ESI): calcd for C 16 H 14 N 2 Na 257.1055 [M + Na] + , found 257.1049. The spectral data were in agreement with those reported previously for this compound …”

Section: Methodssupporting

confidence: 92%

Synthesis of Pyrazoles via Electrophilic Cyclization

2011

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Carbocations

McClelland

2011

Organic Reaction Mechanisms · 2008

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Cycloisomerization of acetylenic oximes and hydrazones under gold catalysis: Synthesis and cytotoxic evaluation of isoxazoles and pyrazoles

et al. 2015

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The synthesis of substituted isoxazoles and pyrazoles through a general cycloisomerization methodology has been reported. The capability of gold(III) chloride to promote cycloisomerization of both α, βacetylenic oximes and α, β-acetylenic hydrazones is the centrepiece of the strategy. A range of acetylenic precursors were investigated to afford 28 examples of the products with good to excellent chemical yields. Selected compounds were screened for their cytotoxic potential towards COLO320 cancer cell lines. The IC 50 values of the tested compounds were in the micromolar range, with the best compound, 5-(6-Methoxy-naphthalen-2-yl)-3-phenyl-isoxazole (3h) displaying an IC 50 of 38.9 μM. For this compound, the crystal structure in complex with Aurora-A kinase was obtained which revealed details of its binding mode within the active site with a free energy of binding-9.54 kcal/mol.

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Reaction of arylhydrazines with an α-alkynyl-carbonylic compound: an unexpected hydration reaction

Cited by 4 publications

References 8 publications

Synthesis of Pyrazoles via Electrophilic Cyclization

Synthesis of Pyrazoles via Electrophilic Cyclization

Carbocations

Cycloisomerization of acetylenic oximes and hydrazones under gold catalysis: Synthesis and cytotoxic evaluation of isoxazoles and pyrazoles

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