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Synthesis of Pyrazoles via Electrophilic Cyclization
Date
2011-08-19
Author
Zora, Metin
KIVRAK, Arif
YAZICI, Ceyda
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Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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Electrophilic cyclizations of alpha,beta-alkynic hydrazones by molecular iodine were investigated for the synthesis of 4-iodopyrazoles. alpha,beta-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, alpha,beta-alkynic hydrazones underwent electrophilic cyclization to afford 4-iodopyrazoles in good to high yields. Iodocyclization was general for a wide range of alpha,beta-alkynic hydrazones and tolerated the presence of aliphatic, aromatic, heteroaromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.
Subject Keywords
Estrogen-receptor modulators
,
Mediated heteroatom cyclizations
,
Fully substituted pyrazoles
,
Highly efficient synthesis
,
Solid-phase synthesis
,
Activity in-vitro
,
One-pot synthesis
,
C pi-bonds
,
Regioselective synthesis
,
Antimalarial activity
URI
https://hdl.handle.net/11511/38041
Journal
JOURNAL OF ORGANIC CHEMISTRY
DOI
https://doi.org/10.1021/jo201119e
Collections
Department of Chemistry, Article