Synthesis of Pyrazoles via Electrophilic Cyclization

2011-08-19
Zora, Metin
KIVRAK, Arif
YAZICI, Ceyda
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.

Citation Formats
M. Zora, A. KIVRAK, and C. YAZICI, “Synthesis of Pyrazoles via Electrophilic Cyclization,” JOURNAL OF ORGANIC CHEMISTRY, vol. 76, no. 16, pp. 6726–6742, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/38041.