Synthesis of 1-acetyl-3,5-diphenyl-1H-pyrazole from Chalcone
2021
Noor Hidayah Pungot | Najwa Amira Mohamad Latif | Nur Ain Nabilah Ash'ari
The synthesis of chalcone has drawn tremendous interest over the past years due to its wide applications in the pharmaceutical and biological sectors. Indeed, this compound is reported to possess a broad spectrum of promising bioactivities, including anti-inflammatory, anti-invasive, antioxidant, antitumor and antibacterial properties. In this work, chalcone 3 was synthesised via Claisen-Schmidt condensation by using a common starting material of benzaldehyde 1 and acetophenone 2 in the presence of alcoholic alkaline base. Subsequently, 3,5-diphenyl-2-pyrazoline 4 intermediate was successfully synthesised by reductive amination reaction of 3 with hydrazine hydrate. Thereafter, insertion of acyl subunit at N-1 position of the corresponding amine via 1N-acylation reaction afforded the targeted 1-acetyl-3,5-diphenyl-1H-pyrazole 5 derivative. The structures of all the synthesised compounds were confirmed by elemental analyses, IR, GC-MS and NMR spectra.
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