Synthesis of Pyrazoles via Electrophilic Cyclization

Date

2011-08-19

Author

Zora, Metin
YAZICI, Ceyda

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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

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Citation Formats

M. Zora and C. YAZICI, “Synthesis of Pyrazoles via Electrophilic Cyclization,” JOURNAL OF ORGANIC CHEMISTRY, pp. 6726–6742, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/38041.