α-Functionalization of the Carbonyl Group for the Construction of Pyrazoline Rings Derived from 1,3-Indandione

Authors

  • Raniah T. Ali Department of Chemistry, College of Science, University of Baghdad, Baghdad, Iraq Al-Jadriya Campus, Baghdad 10071, Iraq
  • Rafid S. Dawood Department of Chemistry, College of Science, University of Baghdad, Baghdad, Iraq Al-Jadriya Campus, Baghdad 10071, Iraq https://orcid.org/0000-0002-7412-0019

DOI:

https://doi.org/10.24996/ijs.2024.65.9.6

Keywords:

Antibacterial, Antioxidant, 1,3-Indandione, Pyrazoline

Abstract

This work includes the synthesis of new pyrazoline derivatives 5-13 over three steps starting from 1,3-indandione. The first step included the acylation of 1,3- indandione with acetyl chloride to produce compound 1 with excellent yield (90%). In the second step, the enolate form of 1 was condensed with various aromatic aldehydes (benzaldehyde, p-nitrobenzaldehyde, and p chlorobenzaldehyde) to afford the corresponding α,β-unsaturated carbonyl derivatives 2-4 in high yields (93-95%). The third step involved a reaction of 2-4 with hydrazine hydrate, phenyl hydrazine, and p-nitrophenyl hydrazine to give the desired pyrazoline derivatives 5-13 in yields ranging from 70 to 83%. The structure of the synthesized compounds was verified through FT-IR and 1H NMR spectroscopy. Additionally, a subset of the synthesized compounds underwent testing to evaluate their antibacterial and antioxidant
properties.

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Published

2024-09-30

Issue

Section

Chemistry

How to Cite

α-Functionalization of the Carbonyl Group for the Construction of Pyrazoline Rings Derived from 1,3-Indandione. (2024). Iraqi Journal of Science, 65(9), 4890-4900. https://doi.org/10.24996/ijs.2024.65.9.6

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