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

Table 6

Spectral data of 2,2-dimethyl-5-(fluorinatedbenzylidene)-1,3-dioxane-4,6-diones (7a–e).

Entry	IR (cm^−1)	^1H NMR (δ ppm)	^13C NMR (δ ppm)
7a	3083 (CH), 1630 (C=O), 1554 (C=C str), 1055 (C–O)	8.97 (s, 1H, CH), 7.70 (d, 2H, Ar-H, 𝐽=8.1 Hz), 7.64 (d, 2H, Ar-H, 𝐽=8.1 Hz), 2.12 (s, 6H, CH3)	164.91 (C=O), 160.42 (C–F), 154.08 (CH), 123.74 (C=C, aliphatic carbon), 134.02–118.12 (aromatic carbons), 105.18 (O–C–O), 26.16 (CH3)
7b	2915 (CH), 1682 (C=O), 1577 (C=C str), 1130 (C–O)	8.42 (s, 1H, CH), 7.61 (d, 2H, Ar-H, 𝐽=8.2 Hz), 7.32 (d, 2H, Ar-H, 𝐽=8.0 Hz), 1.83 (s, 6H, CH3)	164.27 (C–O), 165.46–165.30 (C=O), 150.03 (CH), 124.18 (C=C, aliphatic carbon), 122.42 (CF3), 134.85–120.06 (aromatic carbons), 107.92 (O–C–O), 27.12–26.97 (CH3)
7c	3072 (CH), 1680 (C=O), 1583 (C=C str), 1145 (C–O)	8.77 (s, 1H, CH), 7.88 (d, 2H, Ar-H, 𝐽=7.9 Hz), 7.47 (d, 2H, Ar-H, 𝐽=7.9 Hz), 1.85 (s, 6H, CH3)	167.40–167.30 (C=O), 149.26 (CH), 126.15 (C=C, aliphatic carbon), 122.42 (CF3), 135.05–121.93 (aromatic carbons), 106.94 (O–C–O), 27.72–27.64 (CH3)
7d	3060 (CH), 1685 (C=O), 1584 (C=C str), 1095 (C–O)	8.81 (s, 1H, CH), 7.80 (s, 1H, Ar-H), 7.43 (d, 2H, Ar-H, 𝐽=6.5 Hz), 1.75 (s, 6H, CH3)	166.22–166.10 (C=O), 149.29 (CH), 126.85 (C=C, aliphatic carbon), 123.67 (CF3), 135.95–122.33 (aromatic carbons), 107.04 (O–C–O), 27.72–27.60 (CH3)
7e	2979 (CH), 1680 (C=O), 1590 (C=C str), 1130 (C–O)	8.37 (s, 1H, CH), 7.55 (s, 1H, Ar-H), 7.17 (d, 2H, Ar-H, 𝐽=7.3 Hz), 1.70 (s, 6H, CH3)	165.40–165.30 (C=O), 163.22 (C–F), 146.91 (CH), 127.05 (C=C, aliphatic carbon), 134.35–120.63 (aromatic carbons), 106.97 (O–C–O), 26.50–26.42 (CH3)