Research Article

Green Chemical Synthesis and Analgesic Activity of Fluorinated Thiazolidinone, Pyrazolidinone, and Dioxanedione Derivatives

Table 5

Spectral data of 5-methyl-4-(fluorinatedbenzylidene)-2-phenylpyrazolidin-3-ones (5a–e).

EntryIR (cm−1) 1H NMR (δ) 13C NMR (δ)

5a3129 (CH), 1670 (C=O), 1586 (C=C)7.42 (s, 1H, CH), 7.14–7.30 (comp, 9H, Ar-H), 3.48 (s, 1H, CH), 2.01 (s, 1H, NH), 1.20 (s, 3H, CH3)163.17 (C–F), 161.31 (C=O), 135.33 (CH), 130.48 (C=C, aliphatic carbon), 142.05–115.16 (aromatic carbons), 24.13 (CH3)

5b3073 (CH), 1677 (C=O), 1586 (C=C)7.67 (s, 1H, CH), 7.38–7.20 (comp, 9H, Ar-H), 3.46 (s, 1H, CH), 2.11 (s, 1H, NH), 1.23 (s, 3H, CH3)162.17 (C–O), 161.40 (C=O), 133.68 (CH), 130.83 (C=C, aliphatic carbon), 122 (CF3), 141.85–114.32 (aromatic carbons), 23.93 (CH3)

5c2915 (CH), 1675 (C=O), 1589 (C=C) 7.50 (s, 1H, CH), 7.34–7.17 (comp, 9H, Ar-H), 3.48 (s, 1H, CH), 2.08 (s, 1H, NH), 1.53 (s, 3H, CH3)161.78 (C=O), 135.21 (CH), 130.83 (C=C, aliphatic carbon), 122.54 (CF3), 141.08–115.36 (aromatic carbons), 23.40 (CH3)

5d3060 (CH), 1688 (C=O), 1591 (C=C) 7.73 (s, 1H, CH), 7.19–7.71 (comp, 8H, Ar-H), 3.51 (s, 1H, CH), 2.52 (s, 1H, NH), 1.24 (s, 3H, CH3)162.50 (C=O), 134.82 (CH), 130.82 (C=C, aliphatic carbon), 123.13 (CF3), 139.82–112.12 (aromatic carbons), 21.73 (CH3)

5e3069 (CH), 1678 (C=O), 1590 (C=C)7.62 (s, 1H, CH), 7.38–7.27 (comp, 8H, Ar-H), 3.40 (s, 1H, CH), 2.14 (s, 1H, NH), 1.25 (s, 3H, CH3)161.97 (C–F), 161.54 (C=O), 135.33 (CH), 136.40 (C=C, aliphatic carbon), 141.15–114.16 (aromatic carbons), 23.10 (CH3)