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

Table 4

Spectral data of 5-(fluorinatedbenzylidene)-2-thioxo-1,3-thiazolidin-4-ones (3a–e).

Entry	IR (cm^−1)	^1H NMR (δ ppm)	^13C NMR (δ ppm)
3a	3350 (NH str of amide), 1590 (C=C), 1131 (C=S str), 1680 (C=O)	8.01 (s, 1H, NH), 7.42 (s, 1H, CH), 7.14 (d, 2H, Ar-H, 𝐽=8.2 Hz), 7.30 (d, 2H, Ar-H, 𝐽=8.2 Hz)	200 (C=S), 168.31 (C=O), 142.33 (CH), 120.48 (C=C, aliphatic carbon), 138.25–119.36 (aromatic carbons)
3b	3357 (NH str of amide), 1596 (C=C), 1211 (C=S str), 1682 (C=O)	8.65 (s, 1H, NH), 8.02 (s, 1H, CH), 7.98 (d, 2H, Ar-H, 𝐽=8.0 Hz), 6.79 (d, 2H, Ar-H, 𝐽=8.0 Hz)	200 (C=S), 168.37 (C=O), 161.23 (C–O) 143 (CH), 120.48 (C=C, aliphatic carbon), 122 (CF3), 138.25–119.36 (aromatic carbons)
3c	3348 (NH str of amide), 1578 (C=C), 1168 (C=S str), 1686 (C=O)	8.32 (s, 1H, NH), 7.50 (s, 1H, CH), 7.46 (d, 2H, Ar-H, 𝐽=8.5 Hz), 7.32 (d, 2H, Ar-H, 𝐽=8.5 Hz)	198.55 (C=S), 169.30 (C=O), 143 (CH), 120.48 (C=C, aliphatic carbon), 122.06 (CF3), 138.25–119.92 (aromatic carbons)
3d	3320 (NH str of amide), 1590 (C=C), 1136 (C=S str), 1688 (C=O)	8.62 (s, 1H, NH), 7.50 (s, 1H, CH), 7.43 (s, 1H, Ar-H), 7.26 (d, 2H, Ar-H, 𝐽=8.2 Hz)	201 (C=S), 168.32 (C=O), 143.44 (CH), 121.17 (C=C, aliphatic carbon), 118.56 (CF3), 146.25–120.36 (aromatic carbons)
3e	3342 (NH str of amide), 1584 (C=C), 1161 (C=S str), 1692 (C=O)	8.51 (s, 1H, NH), 7.44 (s, 1H, Ar-H), 7.28 (d, 2H, Ar-H, 𝐽=8.0 Hz)	200 (C=S), 168.37 (C=O), 161.03 (C–F), 143 (CH), 120.48 (C=C, aliphatic carbon), 138.25–119.36 (aromatic carbons)