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

Table 3

Experimental and analytical data of 5-(fluorinatedbenzylidene)-2-thioxo-1,3-thiazolidin-4-ones (3a–e), 5-methyl-4-(fluorinatedbenzylidene)-2-phenylpyrazolidin-3-ones (5a–e), and 2,2-dimethyl-5-(fluorinatedbenzylidene)-1,3-dioxane-4,6-diones (7a–e).

Entry	R	Time (hrs/min)	Yield (%)	M.P. (°C)	Analysis calcd. (found) (%)
					C	H	N
3a	3-F	1.5 hrs	95	132	50.19 (50.04)	2.53 (2.50)	5.85 (5.88)
3b	4-OCF3	1 hrs	90	115	43.28 (43.08)	1.98 (1.95)	4.59 (4.61)
3c	4-CF3	70 min	92	172	45.67 (45.35)	2.09 (2.07)	4.84 (4.82)
3d	2-NO2, 4-CF3	100 min	91	110	39.52 (39.75)	1.51 (1.53)	8.38 (8.35)
3e	2-F, 5-NO2	2 hrs	94	89	42.25 (42.05)	1.77 (1.75)	9.85 (9.81)
5a	3-F	40 min	90	102	72.32 (72.15)	5.36 (5.33)	9.92 (9.95)
5b	4-OCF3	50 min	93	85	62.07 (62.25)	4.34 (4.36)	8.04 (8.00)
5c	4-CF3	1 hrs	94	105	65.06 (65.25)	4.55 (4.52)	8.43 (8.40)
5d	2-NO2, 4-CF3	60 min	90	162	57.30 (57.08)	3.74 (3.72)	11.14 (11.11)
5e	2-F, 5-NO2	70 min	93	180	62.38 (62.20)	4.31 (4.34)	12.84 (12.82)
7a	3-F	1.5 hrs	91	104	62.40 (62.56)	4.43 (4.45)	—
7b	4-OCF3	2 hrs	90	143	53.17 (53.34)	3.51 (3.49)	—
7c	4-CF3	2 hrs	95	164	56.01 (56.22)	3.69 (3.67)	—
7d	2-NO2, 4-CF3	2 hrs	92	110	48.71 (48.51)	2.92 (2.94)	4.06 (4.03)
7e	2-F, 5-NO2	160 min	94	115	52.89 (52.69)	3.41 (3.39)	4.74 (4.71)