N-(Phenylsulfonyl)Benzenesulfonamide: A New Organocatalyst for One-Pot, Solvent-Free Synthesis of Biginelli’s 3,4-Dihydropyrimidine-2(1H)-Thiones

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• General Procedures: Method A: A mixture of β-ketoesters (1 mmol), aldehyde (1 mmol), urea, or thiourea (1.0 mmol), and N-(phenylsulfonyl)benzenesulfonamide (5 mol.%) was stirred at r.t. The reaction was monitored by thin-layer chromatography using EtOAc: Hexane (30:70). On completion of the reaction, it cooled to room temperature and quenched in water, and the product was extracted by ethyl acetate; The organic layer was dried over sodium sulfate and condensed in a vacuum to get pure products. The products obtained were known compounds identified by 1H NMR spectroscopy, and the analytical data were compared with the literature values. Method B: A mixture of β-ketoesters (1 mmol), aldehyde (1 mmol), urea, or thiourea (1.0 mmol), and N-(phenylsulfonyl)benzenesulfonamide (5 mol.%) was kept at 90 °C. The reaction was monitored by thin-layer chromatography using EtOAc: Hexane (30:70). On completion of the reaction, cooled to room temperature and quenched in water, and the product was extracted by ethyl acetate. The organic layer was dried over sodium sulfate and condensed in a vacuum to get pure products. The products obtained were known compounds identified by 1H NMR spectroscopy, and the analytical data were compared with the literature values.
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