Preparation of 2,3-Diarylthiazolidin-4-one Derivatives Using Barium Sulfate Nano-Powders

Figures & data

Scheme 1. Synthesis of 2,3-diarylthiazolidin-4-one derivatives (T₁-T₁₁).

Table 1. Optimization of the reaction conditions in the synthesis of T₉.

Entry	Catalyst (mmol)	T (°C)	Solvent (5 mL)	Yield $\mathbf{\%}$
1	0.18	RT	n-hexane	–
2	0.18	RT	CH2Cl2	25
3	0.18	RT	Et2O	30
4	0.18	RT	EtOAc	51
5	0.18	RT	EtOH	87
6	0.18	RT	MeOH	81
7	0.18	RT	MeCN	75
8	0.18	RT	–	70
9	0.36	RT	EtOH	86
10	0.09	RT	EtOH	78
11	0.05	RT	EtOH	47
12	0.03	RT	EtOH	29
13	–	RT	EtOH	–

RT: room temperature; CH₂Cl₂: dichloromethane; Et₂O: diethyl ether; EtOH: ethanol; EtOAc: ethyl acetate; MeOH: methanol; MeCN: acetonitrile. Reactions were done on a 1 mmol scale.

Table 2. Synthesis of 2,3-diarylthiazolidin-4-one derivatives using BaSO₄ nano-powder as catalyst.

Entry	Chemical Structure	m.p. [Lit. m.p.]^ref (°C)	Time (min)	Yield (%)^a
T1		145-147*	120	77
T2		127-129*	130	60
T3		121-123*	70	85
T4		155-157*	100	72
T5		131-133*	180	83
T6		149-151*	180	65
T7		166-168*	180	55
T8		124-126*	120	60
T9		110-112 [110-112]^28,^37	100	87
T10		121-123 [120-122]^28,^37	80	80
T11		152-154 [151-152]^28,^37	120	71

^aIsolated yield. *Novel derivatives.

Table 3. Comparison results of BaSO₄ with other catalysts reported in the literature.

Entry	Catalyst	Condition	^aYield (%)	Reference
1	Bi(SCH2COOH)3	Solvent-free; 70 °C; 2 h	75	^24
2	H2SO4	Toluene; 100 °C; 5 h	34	^25
3	P-TsOH	Toluene; 100 °C; 5 h	32	^25
4	MsOH	Toluene; 100 °C; 5 h	24	^25
5	HClO4-TiO2	Toluene; 100 °C; 5 h	48	^25
6	Acidic Al2O3	Toluene; 100 °C; 5 h	15	^25
8	TiO2	Toluene; 100 °C; 5 h	8	^25
8	Amberlite	Toluene; 100 °C; 5 h	36	^25
9	Zeolite type Y	Toluene; 100 °C; 5 h	41	^25
10	BaMoO4	EtOH; RT; 2 h	81	^33
11	BaSO4	EtOH; RT; 100 min	87	This study

^aIsolated yield; based on the preparation of 2,3-diphenylthiazolidin-4-one.

Figure 1. Reusability of BaSO₄ nano-powder.

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