Synthesis of Pyrazoles via Cul-Mediated Electrophilic Cyclizations of alpha,beta-Alkynic Hydrazones
JOURNAL OF ORGANIC CHEMISTRY, cilt.76, sa.22, ss.9379-9390, 2011 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 76 Sayı: 22
- Basım Tarihi: 2011
- Doi Numarası: 10.1021/jo201685p
- Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
- Sayfa Sayıları: ss.9379-9390
- Eskişehir Osmangazi Üniversitesi Adresli: Hayır
Özet
Synthesis of pyrazoles via electrophilic cyclization of alpha,beta-alkynic hydrazones by copper(I) iodide is described. When treated with copper(I) iodide in the presence of triethylamine in refluxing acetonitrile, alpha,beta-alkynic hydrazones, prepared readily from hydrazines and propargyl aldehydes and ketones, undergo electrophilic cyclization to afford pyrazole derivatives in good to excellent yields. The reaction appears to be general for a variety of alpha,beta-alkynic hydrazones and tolerates the presence of aliphatic, aromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.