* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With piperidine In ethanol at 90℃; Inert atmosphere
General procedure: The appropriate aldehyde (1 equiv) was added to EtOH (3 mL/0.2 mmol) and the mixture was stirred until complete solution. Theoxindole (1 equiv) and piperidine (0.1 equiv) were added, and themixture was heated to 90°C for 3-7 h, and cooled. The resultingprecipitatewas filtered, washed with cold ethanol and dried to givethe pure compound. If necessary, additional recrystallization inethanol was applied to obtain the pure product.
Reference：
[1] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 286 - 307
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 5, p. 2077 - 2090
[3] Journal of Chemical Research, 2018, vol. 42, # 5, p. 244 - 246
2
[ 59-48-3 ]
[ 459-57-4 ]
[ 3476-86-6 ]
[ 90828-17-4 ]
Yield
Reaction Conditions
Operation in experiment
25%
With piperidine In ethanol for 3 h; Reflux
General procedure: The preparation of compounds 3-25 was carried out by refluxing oxindole with different aromatic aldehydes in ethanol in the presence of a catalytic amount of piperidine were refluxed for 3 h. After cooling reaction mixture was concentrated at reduced pressure to obtain solid of 3-oxindole derivatives, then washed with 1:1 mixture of hexane-ethyl acetate (25 mL) and dried to afford titles compoundsin good yields (Table 1). Only in two cases (10 and21), both E and Z isomers were obtained, these isomers wereseparated by column chromatography using 1:9 ethyl acetate: hexane as eluent. The structures of synthetic compounds 3-25 were elucidated by 1H NMR and EI MS. Elemental analysis results were also found to be satisfactory.
With 1-deoxy-1-(methylamino)-D-glucitol; In ethanol; water; at 78℃; for 1.0h;
General procedure: Meglumine (0.4mmol) was taken in a ethanol:water (1ml:1ml) mixture then aldehyde (1mmol) and oxindole (1mmol) were added at 78 oC. The progress of the reaction wasmonitored by TLC (Silica gel, 7:3, Hexane:EtOAc). There was a formation of yellowprecipitate. After completion of the reaction, precipitate was filtered and washed with waterand recrystallization in EtOH. Product characterization was done by HRMS, 1H NMR and 13CNMR.
85%
With piperidine; In ethanol; at 90℃;Inert atmosphere;
General procedure: The appropriate aldehyde (1 equiv) was added to EtOH (3 mL/0.2 mmol) and the mixture was stirred until complete solution. Theoxindole (1 equiv) and piperidine (0.1 equiv) were added, and themixture was heated to 90C for 3-7 h, and cooled. The resultingprecipitatewas filtered, washed with cold ethanol and dried to givethe pure compound. If necessary, additional recrystallization inethanol was applied to obtain the pure product.
With triethylamine; In methanol; at 60℃; for 3.0h;
General procedure: A mixture of isatin (0.1 mmol), methyl glycinate 2a (1.0 eq.), methyleneindolinone 3a (1.0 eq.), Et3N (1.0 eq.), in methanol (1.0 mL) was stirred for 3 h at 60 C. After completion of the reaction (TLC), the solvent was removed under vacuum. The crude product was subjected to column chromatography on silica gel using pet/ethyl acetate (2:1) as the eluent to give 4a (43.4 mg, 99% yield).
With triethylamine; In methanol; at 60℃; for 3.0h;
General procedure: A mixture of isatin (0.1 mmol), methyl glycinate 2a (1.0 eq.), methyleneindolinone 3a (1.0 eq.), Et3N (1.0 eq.), in methanol (1.0 mL) was stirred for 3 h at 60 C. After completion of the reaction (TLC), the solvent was removed under vacuum. The crude product was subjected to column chromatography on silica gel using pet/ethyl acetate (2:1) as the eluent to give 4a (43.4 mg, 99% yield).
With triethylamine; In methanol; at 60℃; for 3.0h;
General procedure: A mixture of isatin (0.1 mmol), methyl glycinate 2a (1.0 eq.), methyleneindolinone 3a (1.0 eq.), Et3N (1.0 eq.), in methanol (1.0 mL) was stirred for 3 h at 60 C. After completion of the reaction (TLC), the solvent was removed under vacuum. The crude product was subjected to column chromatography on silica gel using pet/ethyl acetate (2:1) as the eluent to give 4a (43.4 mg, 99% yield).
General procedure: The preparation of compounds 3-25 was carried out by refluxing oxindole with different aromatic aldehydes in ethanol in the presence of a catalytic amount of piperidine were refluxed for 3 h. After cooling reaction mixture was concentrated at reduced pressure to obtain solid of 3-oxindole derivatives, then washed with 1:1 mixture of hexane-ethyl acetate (25 mL) and dried to afford titles compoundsin good yields (Table 1). Only in two cases (10 and21), both E and Z isomers were obtained, these isomers wereseparated by column chromatography using 1:9 ethyl acetate: hexane as eluent. The structures of synthetic compounds 3-25 were elucidated by 1H NMR and EI MS. Elemental analysis results were also found to be satisfactory.
(Z)-2-(4-fluorophenyl)-2-(2-oxoindolin-3-ylidene)acetonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%
With potassium carbonate; potassium hydroxide; In water; acetonitrile; at 80℃; for 3.0h;
General procedure: The mixture of (E)-3-arylideneindolin-2-ones (0.5mmol), benzoyl cyanide (0.6mmol), potassium carbonate (0.5mmol), potassium hydroxide (0.5mmol) and water (1.0mmol) in acetonitrile (5mL) was stirred at 80C for 3h. The reaction was monitored by TLC. After the completion of the reaction, the mixture was extracted with ethyl acetate (3×10mL), and the resulting solution was washed with saturated brine (3×10mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was isolated by column chromatography using petroleum ether and ethyl acetate (v/v 3:1) as eluent to give pure product. The analytical data for products are given below.
4′-hydroxy-2′-(4-fluorophenyl)-4′,5′-dihydro-2′H-spiro[oxindole-3,3′-thiophen]-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
72.2%
In neat (no solvent); at 20℃;Milling; Green chemistry;
General procedure: (E)-3-arylideneindole-2-ones 1 (1.0 mmol) and 1,4-dithiane-2,5-diol (1.0 mmol) was added into a mortar containing the triethylamine (3 mmol). The resulting reaction mixture was ground at room temperature. After completion of the reaction as monitored by TLC,the mixture was purified by column chromatography on silica gelusing petroleum ether and ethyl acetate (3:1, V/V) as eluent and recrystallised from ethyl alcohol to afford the corresponding product 2.
(Z)-2-(4-fluorophenyl)-2-(2-oxoindolin-3-ylidene)acetonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
92%
With cerium(III) chloride heptahydrate; potassium hydroxide; In water; at 100℃; for 2.0h;Green chemistry;
General procedure: The mixture of (E)-3-arylideneindolin-2-ones (1 mmol), TMSCN (1.2 mmol), KOH(1 mmol), CeCl37H2O (0.1 mmol), and water (5 mL) was stirred at 100 C for 2 h. Thereaction was monitored by TLC. After the completion of the reaction, the solid was filteredand washed with 15mL of water, and recrystallized from EtOAc to afford thepure products.
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