S. Kaping, U. Kalita, M. Sunn
Jan 19, 2016
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Journal
Monatshefte für Chemie - Chemical Monthly
Abstract
An environmentally benign, simple, efficient, and convenient route is described for the synthesis of novel pyrazolo[1,5-a]pyrimidine derivatives under ultrasound irradiation assisted by KHSO4 in aqueous medium. 3-(4-Methoxyphenyl)-3-oxopropanenitrile reacted with hydrazine hydrate in refluxing ethanol to give 5-(4-methoxyphenyl)-1H-pyrazol-3-amine. Condensation of 3-aminopyrazoles with formylated active proton compounds furnished pyrazolopyrimidines in high to excellent yield. The chemical structure and regioselectivity of the synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, and mass spectral data. X-ray crystallographic study of a selected compound was performed. Furthermore, these synthesized compounds were screened for their anti-inflammatory and anti-cancer activity and the results were promising. The major advantages of this protocol afford high yields, operational simplicity, short reaction times, and devoid of harsh reaction conditions.Graphical abstract