All of the reagents were purchased from Aldrich-reagent and used without further purifications. 1 H NMR spectra and 13 C NMR spectra were recorded on a Bruker Advance III 500 MHz spectrometer and using DMSO-d 6 (500 MHz for 1 H or 125 MHz for 13 C, respectively) as solvent. Chemical shifts of 1 H and 13 C NMR spectra were expressed in δ values (ppm) downfield from tetramethylsilane. Microanalyses were taken on a VARIOX Elemental Analyzer. Mass spectra were carried out on VARIAN1200. IR spectra were obtained on a TENSOR 27 spectrometer. Melting points were recorded on microscope (SGW X-4) melting point apparatus. The reaction was monitored by TLC.
Experimental details and characterizationGeneral procedure for preparation of oxindole derivatives 3a-3p and 5a-5e A mixture of the isatin 1 or acenaphthenequinone 4 (1 mmol), indole 2 (2 mmol), p-TSA (10 mol %), CH 2 Cl 2 (10 mL) was added to 50 mL flask and stirred at room temperature until the the completion of the reaction (Scheme 1, 2). Then the solid was filtered and washed with CH 2 Cl 2 (5 mL) and ethanol (5 mL) in turns, affording the product in excellent yields, which was recrystallized from ethanol to produce pure crystalline products. The products were identified by elemental analysis, MS, 1 H NMR, 13 C NMR, and IR spectra. Scheme 1. Preparation of product 3a-3p Scheme 2. Preparation of product 5a-5e Spectroscopic and characterization data 3,3-di(1H-indol-3-yl)indolin-2-one (3a): Yield: 92%; white solid; m. p. 318-320 (lit. [26]
An efficient mild one-pot synthesis of spiro [indoline-3,4'-pyrano[2,3-c]pyrazole derivatives by a four-component reaction of hydrazine, a β-keto ester, isatin, and malononitrile catalysed by L-proline in water is reported.
An efficient synthesis of spiro [indoline-3,7′-pyrrolo[1,2-c]imidazole] is achieved through a three-component reaction of isatins, malononitrile, and hydantoin/2-thiohydantoin in water catalysed by NaHCO 3 . All the target compounds were screened for the Cell Division Cycle 25 Phosphatase B (CDC25B) inhibitory activities.
Rapid and Efficient Synthesis of 3,3-Di(1H-indol-3-yl)indolin-2-ones and 2,2-Di(1H-indol-3-yl)-2H-acenaphthen-1-onesCatalyzed by p-TSA. -The title compounds (III) and (V) are obtained by reaction of various isatins or acenaphthenequinone, resp., with indoles under mild reaction conditions. -(YU, J.; SHEN, T.; LIN, Y.; ZHOU, Y.; SONG*, Q.; Synth.
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