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.
A Green, Facile Approach for the Multicomponent Synthesis of Bioactive Spiro[indoline-3,7'-pyrrolo[1,2-c]imidazole] Derivatives. -A variety of the title spiro-compounds (IV) (17 examples) are synthesized via a NaHCO 3-catalyzed three-component reaction. Some of them, e.g. compound (IVf), show much higher activities in the screening for the cell division cycle 2 phosphatase B (CDC25B) than the standard drug Na3VO4. -(SHEN, T.; ZHOU, Y.; CHE, F.; YU, J.; LIN, Y.; SONG*, Q.; J. Chem. Res. 39 (2015) 2, 115-119, http://dx.doi.org/10.3184/174751915X14229612721445 ; State Key Lab. Breed.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.