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CAS No. : | 1217-89-6 | MDL No. : | MFCD00187663 |
Formula : | C15H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SIISFRLGYDVIRG-UHFFFAOYSA-N |
M.W : | 237.25 | Pubchem ID : | 264734 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | at 70℃; for 12 h; | To a 10-mL oven-dried vial containing a magnetic stirring bar, isatin 2a (35.6 mg,0.15 mmol), and PhCF3 (1.0 mL), was added a solution of diazo compound 1a (52.6mg, 0.3 mmol) in PhCF3 (1.0 mL) via a syringe pump in 50 min at 90 oC. After the addition, the reaction mixture was monitored by proton NMR after the solvent was evaporated in vacuo at different reaction times (the time including the 50 min for the addition of 1a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With acetic acid; In ethanol;Reflux; | A synthesis of Schiff's bases of isatin derivative and carbohydrzide of nalidixic acid to result in compounds according to formula (I) can be conducted as follows:; A stirred mixture of appropriate isatin derivative (compound II, 0.5 mmol) and carbohydrazide of nalidixic acid (compound III 0.12 g, 0.5 mmol) in ethanol as acidified with 4 drops of glacial acetic acid is refluxed for a specific time (4-13 hours), and the reaction progress is monitored by thin layer chromatography (TLC). The reaction mixture is then concentrated, cooled and filtered. The filtrate is either crystallized by an appropriate solvent or washed thoroughly with ethanol.A compound according to formula (I) with RH and R1H (N'-(1-benzyl-2-oxoindolin-3-ylidene)-1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carbohydrazid was prepared and the following analytical data was received:Yield: 55%; m.p. 292 C. (from DCM). IRvmax/cm-1 1441.03 (N-N), 1466.24, 1489.30 (C-N), 1510.87, 1541.11 (CN), 1611.46, 1679.65 (CO amidic), 2926.03 (C-H aliphatic), 3058.36 (C-H aromatic), 3446.27 (N-H). 1H NMR deltaH(CDCl3) 1.58 (3H, t, J=6,5, N1'CH2CH3), 2.73 (3H, s, C7'CH3), 4.63 (2H, q, J=7.5, N1'CH2CH3), 5.08 (2H, s, N1CH2ph), 6.76 (1H, d, J, =8, C7H), 7.12 (1H, t, J=7.5, C5H), 7.29-7.39 (7H, m, C4H, C6H and phenyl protons), 7.93 (1H, d, J=7.5, C6'H), 8.88 (1H, d, J=8.5, C5'H), 9.07 (1H, s, C2'H), 15.42 (1H, s, CONH). 13C NMR deltaC (DMSO-d6): 15.38 (N1'CH2CH3), 25.19 (C7'CH3), 43.44 (N1CH2ph). 47.07 (N1'CH2CH3), 110.03 (C7), 110.94 (C5'), 120.01 (C3a), 120.37 (C6'), 121.43 (CO, 121.92 (C5), 122.27 (C4), 127.39, 127.83, 128.93, 132.68, 135.73, 135.84 (phenyl carbons), 131.39 (C3'), 136.45 (C3), 137.69 (C6), 144.03 (C2'), 148.48 (C8a'), 149.37 (C7a), 163.12 (C2), 163.72 (C7'), 164,24 (C9'), 176.55 (C4'). MS m/z(%): 43.8 (100%), 90.7 (1.21%), 103.0 (6.91%), 104.1 (8.54%), 117.0 (7.58%), 131.2 (0.78%), 132.8 (22.71%), 145.8 (3.19%), 159.8 (8.66%), 173.1 (1.85%), 188.4 (2.32%), 201.9 (1.30%), 210.2 (6.92%), 214.5 (1.80%), 230.3 (1.16%), 231.4 (0.99%), 238.7 (0.54%), 246.8 (22.17%), 332.2 (3.31%), 346.2 (2.25%), 464.6 (0.45%), 465.8 (2,71%), 466.9 (2.25%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a solution of phosphinothiourea 1b (0.02 mmol) in THF (1.0 mL) was added acrylate (0.4 mmol) at 0 C. After 10 min stirring at this temperature, isatin (0.2 mmol) was added. The reaction mixture was stirred at 0 C (monitoring by TLC). Then the resulting solution was concentrated under reduced pressure and the residue was purified by a flash column chromatography on silica gel to afford the desired adducts and the ee values were determined by HPLC analysis with chiral column. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: 2-bromo-5-methyl thiophene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: 1-benzylisatin In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In 1,4-dioxane Inert atmosphere; Reflux; | |
In 1,4-dioxane for 6h; Reflux; | ||
In toluene for 10h; Sealed tube; |
In 1,4-dioxane Reflux; Inert atmosphere; | ||
In 1,4-dioxane Reflux; Inert atmosphere; | ||
In 1,4-dioxane for 12h; Reflux; | ||
In 1,4-dioxane at 120℃; for 12h; | ||
In 1,4-dioxane Inert atmosphere; Reflux; | ||
Reflux; Inert atmosphere; | ||
In 1,4-dioxane for 18h; Reflux; Inert atmosphere; | ||
In 1,4-dioxane Inert atmosphere; Reflux; | ||
In 1,4-dioxane Reflux; Inert atmosphere; | ||
In toluene for 24h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With C57H70NOP; palladium diacetate; beta-naphthol; potassium hydroxide; In tetrahydrofuran; at 20℃; for 48h; | General procedure: A solution of Pd (OAc)2 (2.25 mg, 0.01 mmol) and (Sa,S)-8g(9.78 mg, 0.012 mmol) in THF (1.0 mL) was stirred for 30 min atroom temperature. KOH (11.2 mg, 0.2 mmol), isatins (0.20 mmol),arylboronic acids (0.4 mmol) and additives (0.03 mmol) were addedsuccessively with additional THF (1.0 mL). The resulting mixturewas stirred for 48 h at room temperature. Then the solvent wasremoved under vacuum and the residue was purified by flash columnchromatography using silica gel with ethyl acetate/petroleumether as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With C57H70NOP; palladium diacetate; beta-naphthol; potassium hydroxide; In tetrahydrofuran; at 20℃; for 48h; | General procedure: A solution of Pd (OAc)2 (2.25 mg, 0.01 mmol) and (Sa,S)-8g(9.78 mg, 0.012 mmol) in THF (1.0 mL) was stirred for 30 min atroom temperature. KOH (11.2 mg, 0.2 mmol), isatins (0.20 mmol),arylboronic acids (0.4 mmol) and additives (0.03 mmol) were addedsuccessively with additional THF (1.0 mL). The resulting mixturewas stirred for 48 h at room temperature. Then the solvent wasremoved under vacuum and the residue was purified by flash columnchromatography using silica gel with ethyl acetate/petroleumether as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 20℃; for 24h;Mechanism; | General procedure: Under ambient atmosphere, isatin 1 or 50% ethyl glyoxalate in toluene (0.2 mmol), allenoate 2 (0.4 mmol) and isoquinoline 3 (0.4 mmol) were stirred in 1.0 mL of DCM at room temperature until the reaction was completed. The solvent was removed under reduced pressure and the residue was purified by a flash column chromatography (SiO2) to give the corresponding products 4a-4m in medium yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With ammonium acetate; at 200℃; for 1h;Microwave irradiation; Molecular sieve; Green chemistry; | General procedure: To a 10-mL snap-cap microwave reaction vial, equipped with a magnetic stir bar and about 200 mg of activated 3Å molecular sieves, ethyl 4-(1H-indole-3-yl)-4-oxobutanoate (0.10 g, 0.4 mmol), isatin (0.070 g, 0.47 mmol), anhydrous ammonium acetate (0.126 g, 1.6 mmol), and polyethylene glycol (PEG-200, 3mL) were added. The reaction mixture was heated at 200 C (power = 200 W) in the microwave for 1 hour. Once cooled, the resulting mixture was quenched over 20 mL of ice water and the organics were extracted in ethyl acetate (2 x 20 mL) and washed with brine (2 x20 mL). The organics were dried over MgSO4, and concentrated under reduced pressure to a dark purple solid. The crude product was purified by silica column chromatography (20% to 50% EtOAc in hexanes, gradient) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 25℃; for 0.0833333h;Inert atmosphere; | General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 × 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 25℃; for 0.0833333h;Inert atmosphere; | General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 × 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid; In toluene;Heating; | General procedure: Isatin (10 mmol), <strong>[373-88-6]2,2,2-trifluoroethylamine hydrochloride</strong> (15 mmol) and p-toluenesulfonic acid (0.5mmol) were suspended in toluene (10 mL) in a two-neck flask with a water separator and a condenser.The mixture was then heated to separate the water until complete disappearance of the starting materials.After cooling to room temperature, the mixture was washed with a small quantity of saturated NaHCO3solution and dried by Na2SO4, After evaporation of the organic solvent, the crude residue was purified byflash chromatography (silica gel, hexane/EtOAc) and afforded the resulting ketimine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 1,4-diaza-bicyclo[2.2.2]octane In water at 20℃; for 1.5h; | |
90% | In water at 50℃; for 0.75h; Green chemistry; | |
In water at 60℃; for 2h; |
In water at 50℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium carbonate In water; N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With [HMIm][HSO4] immobilized Fe3O4 on MCM-41-SO3H nanoparticles; In neat (no solvent); at 100℃; for 0.25h; | General procedure: A mixture of alpha or beta-naphtol (1 mmol), isatin derivatives (1 mmol),barbituric acid (1.2 mmol), and Fe3O4MCM-41-SO3H[HMIm][HSO4](0.08 g) was stirred at 100 C under solvent-free conditions. Thereaction products were monitored using thin-layer chromatography(TLC). After completion of the reaction, magnetic nanocompositeswere separated by a magnet (1.4 T), and the reaction mixture filteredoff. Then, 5 mL distilled waterwas added into the beaker and the obtainedprecipitatewas filtered off. Finally, the crude productswere recrystallizedby ethanol to give pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With [HMIm][HSO4] immobilized Fe3O4 on MCM-41-SO3H nanoparticles; In neat (no solvent); at 100℃; for 0.416667h; | General procedure: A mixture of alpha or beta-naphtol (1 mmol), isatin derivatives (1 mmol),barbituric acid (1.2 mmol), and Fe3O4MCM-41-SO3H[HMIm][HSO4](0.08 g) was stirred at 100 C under solvent-free conditions. Thereaction products were monitored using thin-layer chromatography(TLC). After completion of the reaction, magnetic nanocompositeswere separated by a magnet (1.4 T), and the reaction mixture filteredoff. Then, 5 mL distilled waterwas added into the beaker and the obtainedprecipitatewas filtered off. Finally, the crude productswere recrystallizedby ethanol to give pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With Fe3O4(at)MCM-41-SO3H(at)1-methylimidazolium hydrogen sulfate; In neat (no solvent); at 100℃; for 0.75h; | General procedure: A mixture of alpha or beta-naphthol (1 mmol), isatin derivatives (1 mmol), cyclic 1,3-dicabonyls (1.2 mmol), and Fe3O4MCM-41-SO3H[HMIm][HSO4] (0.08 g) was stirred at 100 C under solvent-free conditions. The reaction products were monitored using thin-layer chromatography (TLC). After completion of the reaction, magnetic nanocomposites were separated by a magnet (1.4 T), and the reaction mixture filtered off. Then, 5 mL distilled water was added into the beaker and the obtained precipitate was filtered off. Finally, the crude products were recrystallized by ethanol to give pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With Fe3O4(at)MCM-41-SO3H(at)1-methylimidazolium hydrogen sulfate; In neat (no solvent); at 100℃; for 0.75h; | General procedure: A mixture of alpha or beta-naphthol (1 mmol), isatin derivatives (1 mmol), cyclic 1,3-dicabonyls (1.2 mmol), and Fe3O4MCM-41-SO3H[HMIm][HSO4] (0.08 g) was stirred at 100 C under solvent-free conditions. The reaction products were monitored using thin-layer chromatography (TLC). After completion of the reaction, magnetic nanocomposites were separated by a magnet (1.4 T), and the reaction mixture filtered off. Then, 5 mL distilled water was added into the beaker and the obtained precipitate was filtered off. Finally, the crude products were recrystallized by ethanol to give pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With acetic acid In methanol for 6h; Reflux; | 3 Synthesis of ligands (L1-L3) General procedure: Step 2: N(4)-cyclohexylthiosemicarbazide (0.173 g, 0.001 mol)was dissolved in methanol (20 mL) and was added to the appropriateketone’s [1-(prop-2-yn-1-yl)indoline-2,3-dione (0.185 g, 0.001 mol); 1-allylindoline-2,3-dione (0.187 g, 0.001 mol) and 1-benzylindoline-2,3-dione (0.237 g, 0.001 mol)] dissolved in methanol(20 mL), reflux continuously for 6 h after a few drops of aceticacid. The yellow product formed was filtered off, washed with coldethanol, and dried in vacuo. It was recrystallized from CH3OH/C2H3N mixture (1:1) to get yellow colored crystals suitable for Xraystudies were obtained from slow evaporation of the reactionmixture for 10-15 days in all three cases. |
79% | With acetic acid In ethanol at 75℃; for 3h; | 3 Synthesis of benzylisatin substituted thiosemicarbazones (1-5) General procedure: The benzylisatin substituted thiosemicarbazones were synthesizedusing the standard procedure [16]. Unsubstituted/substitutedthiosemicarbazide (1 mmol) and benzyl isatin (1 mmol) weresuspended in ethanol (20 mL) containing a few drops of glacialacetic acid. The mixture was refluxed for 3 h and cooled to roomtemperature. The yellow product formed was filtered off, washedwith cold ethanol and ether, and dried in vacuo. It was recrystallizedfrom ethanol to get crystals of the title compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: 2-(4-methylbenzylidene)malononitrile With Hexamethylphosphorous triamide In dichloromethane at -20℃; for 0.333333h; Stage #2: 1-benzylisatin In dichloromethane at -20 - 20℃; for 12h; diastereoselective reaction; | 1 General procedure for the reaction of arylidene pivaloylacetonitrile with isatins General procedure: To a 50mL round flask was added arylidene malononitrile, or arylidene pivaloylacetonitrileor isatylidene malononitrile (1.05mmol) and dry methylene dichloride (10.0mL). The solution was cooled to about -20°C and P(NMe2)3 (1.05mmol) was added and the mixture was stirred for about 20min. Then, the solid of isatin (1.0mmol) was added in portions in about 10min. The solution was stirred at room temperature for about 12h. The solvent was evaporated at reduced pressure. The residue was titrated with methanol to give the crude solid, which was recrystallized in ethanol to give pure product for analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetracarboxymethoxycalix[4]arene; In water; at 80℃; for 12h;Green chemistry; | General procedure: Mixture of 1.0 equivalent of each of dimedone (1 mmol), N-allylisatin (1 mmol) and p-toluidine (1 mmol) were heated with stirring in presence of 5 mol% calixarene C4A4 in 3 ml of H2O. The completion of the reaction was indicated by the disappearance of the starting materials in thin layer chromatography. After completion of the reaction, the reaction mixture was filtered. The residue was further stirred with 1 ml water and filtered. The crude product was recrystallized from ethyl acetate. The two filtrate parts were taken together for further catalyst recycling purpose. The products were characterized by standard analytical techniques such as 1H & 13C NMR, FTIR, elemental analysis, melting point determination and all gave satisfactory results. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With triethylamine; In ethanol; at 40℃; for 2h; | The 1-benzyl-isatin (2.37g, 10mmol) and 6-bromo -2,3-dihydro-quinolin-4-one (2.26g, 10mmol) is dissolved in Anhydrous ethanol (10 ml) in, then adding triethylamine (0.5 ml), heating the system to 40 C, stirring reaction 2h, the separated solid filtering, anhydrous ethanol (2×1 ml) washing, vacuum drying, to get the yellow solid 3.65g, yield 79%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With triethylamine; In ethanol; at 40℃; for 2h; | The 1-benzyl-isatin (2.37g, 10mmol) and 6-chloro -2,3-dihydro-quinolin-4-one (1.81g, 10mmol) is dissolved in Anhydrous ethanol (10 ml) in, then adding triethylamine (0.5 ml), heating the system to 40 C, stirring reaction 2h, the separated solid filtering, anhydrous ethanol (2×1 ml) washing, vacuum drying, to get the yellow solid 3.21g, yield 77%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With potassium tert-butylate; In toluene; at 20℃;Inert atmosphere; | General procedure: To a solution of an alkyne 2 (1.2 equiv) in anhydrous toluene (3 mL) under an argon atmosphere, KOtBu (1.0 equiv) was added, and the mixture was stirred for 10-15 min. Then, an N-protected isatin 1 (1.0 equiv) was added to the reaction mixture, which was stirred for 30 min to 3 h until all the isatin was consumed (confirmed by TLC). The reaction was finally quenched with a few drops of 1 N HCl and the resulting mixture was extracted with CH2Cl2 (2 × 15 mL). The combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was then purified by column chromatography on silica gel (EtOAc-hexane,10:90 to 30:70) to give compounds 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With potassium tert-butylate; In toluene; at 20℃;Inert atmosphere; | General procedure: To a solution of an alkyne 2 (1.2 equiv) in anhydrous toluene (3 mL) under an argon atmosphere, KOtBu (1.0 equiv) was added, and the mixture was stirred for 10-15 min. Then, an N-protected isatin 1 (1.0 equiv) was added to the reaction mixture, which was stirred for 30 min to 3 h until all the isatin was consumed (confirmed by TLC). The reaction was finally quenched with a few drops of 1 N HCl and the resulting mixture was extracted with CH2Cl2 (2 × 15 mL). The combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was then purified by column chromatography on silica gel (EtOAc-hexane,10:90 to 30:70) to give compounds 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With potassium tert-butylate; In toluene; at 20℃;Inert atmosphere; | General procedure: To a solution of an alkyne 2 (1.2 equiv) in anhydrous toluene (3 mL) under an argon atmosphere, KOtBu (1.0 equiv) was added, and the mixture was stirred for 10-15 min. Then, an N-protected isatin 1 (1.0 equiv) was added to the reaction mixture, which was stirred for 30 min to 3 h until all the isatin was consumed (confirmed by TLC). The reaction was finally quenched with a few drops of 1 N HCl and the resulting mixture was extracted with CH2Cl2 (2 × 15 mL). The combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was then purified by column chromatography on silica gel (EtOAc-hexane,10:90 to 30:70) to give compounds 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With zirconium(IV) chloride; In ethanol;Reflux; | General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 1-benzylisatin; triphenyl(t-butoxycarbonylimino)phosphorane In 1,4-dioxane Schlenk technique; Reflux; Inert atmosphere; Stage #2: α-naphthol With C34H40N4O3 In dichloromethane at -20℃; for 18h; Molecular sieve; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With chloroauric acid; In water; for 0.5h;Reflux; | General procedure: Water (15 mL) was added to a mixture of 1.0 mmol of isatin derivative, 1.2 mmol of <strong>[60-27-5]creatinine</strong> (for 2p, 2.3 mmol of <strong>[60-27-5]creatinine</strong>) and 1 mol% of HAuCl4 and the resulting suspension was heated to reflux for 30 min. The clear reaction mixture was cooled to 15-20 C. The precipitated aldol product was filtered and washed with copious amount of water and then with methanol and ethyl acetate (EtOAc). The obtained product was thoroughly dried under vacuum to afford the pure product 2a-2p. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10 % de | With potassium carbonate; 1,3-bis(mesityl)imidazolium chloride; sodium chloride In water at 20℃; for 0.5h; Inert atmosphere; Sealed tube; Overall yield = 76 %; | 2.1. Synthesis of spirooxindole-γ-butyrolactone (3a-h, 4a) using NHC-organocatalysis General procedure: A 10 mL reaction vial was charged with isatin derivatives (0.15mmol), substituted cinnamaldehyde (0.15mmol) and brine (3mL). To this well-stirred mixture, potassium carbonate (0.069g, 0.5mmol) and NHC-A (0.017g, 0.05mmol) were added. The reaction vial was closed with rubber septa and purged with nitrogen. After purging for 5 min, the reaction vial was tightly sealed with crimper cap and allowed to stir for 30 min at room temperature. After completion of 30 min, the reaction mixture was extracted with ethyl acetate (3×10mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The afforded crude mixture was purified by flash chromatography on silica gel (200-400 mesh) in 30% ethyl acetate in hexanes to afford the product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30.612 % de | With potassium carbonate; 1,3-bis(mesityl)imidazolium chloride; sodium chloride In water at 20℃; for 0.5h; Inert atmosphere; Sealed tube; Overall yield = 71 %; | 2.1. Synthesis of spirooxindole-γ-butyrolactone (3a-h, 4a) using NHC-organocatalysis General procedure: A 10 mL reaction vial was charged with isatin derivatives (0.15mmol), substituted cinnamaldehyde (0.15mmol) and brine (3mL). To this well-stirred mixture, potassium carbonate (0.069g, 0.5mmol) and NHC-A (0.017g, 0.05mmol) were added. The reaction vial was closed with rubber septa and purged with nitrogen. After purging for 5 min, the reaction vial was tightly sealed with crimper cap and allowed to stir for 30 min at room temperature. After completion of 30 min, the reaction mixture was extracted with ethyl acetate (3×10mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The afforded crude mixture was purified by flash chromatography on silica gel (200-400 mesh) in 30% ethyl acetate in hexanes to afford the product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In methanol; at 30℃; for 12h; | General procedure: Isatin (1, 0.20mmol, 1 equiv.), amino acid (2, 0.40 mmol, 2 equiv.), methyleneindolinone (3, 0.2mmol, 1 equiv.) and MeOH (0.2 mL or 1 mL) were well mixed and stirred at 30C. Once the reaction was completed (monitored by TLC), the resulting residue was purified by flash column chromatography on silica gel to yield the corresponding product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In methanol at 30℃; for 36h; diastereoselective reaction; | 3.21 General procedure for synthesis of pyrrolidinyldispirooxindole 44.3.1 General procedure: Isatin (1, 0.20mmol, 1 equiv.), amino acid (2, 0.40 mmol, 2 equiv.), methyleneindolinone (3, 0.2mmol, 1 equiv.) and MeOH (0.2 mL or 1 mL) were well mixed and stirred at 30°C. Once the reaction was completed (monitored by TLC), the resulting residue was purified by flash column chromatography on silica gel to yield the corresponding product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol; at 30℃; for 12h; | General procedure: Isatin (1, 0.20mmol, 1 equiv.), amino acid (2, 0.40 mmol, 2 equiv.), methyleneindolinone (3, 0.2mmol, 1 equiv.) and MeOH (0.2 mL or 1 mL) were well mixed and stirred at 30°C. Once the reaction was completed (monitored by TLC), the resulting residue was purified by flash column chromatography on silica gel to yield the corresponding product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In methanol; at 30℃; for 48h; | General procedure: Isatin (1, 0.20mmol, 1 equiv.), amino acid (2, 0.40 mmol, 2 equiv.), methyleneindolinone (3, 0.2mmol, 1 equiv.) and MeOH (0.2 mL or 1 mL) were well mixed and stirred at 30C. Once the reaction was completed (monitored by TLC), the resulting residue was purified by flash column chromatography on silica gel to yield the corresponding product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | In methanol; at 30℃; for 48h; | General procedure: Isatin (1, 0.20mmol, 1 equiv.), amino acid (2, 0.40 mmol, 2 equiv.), methyleneindolinone (3, 0.2mmol, 1 equiv.) and MeOH (0.2 mL or 1 mL) were well mixed and stirred at 30C. Once the reaction was completed (monitored by TLC), the resulting residue was purified by flash column chromatography on silica gel to yield the corresponding product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In methanol; at 30℃; for 12h; | General procedure: Isatin (1, 0.20mmol, 1 equiv.), amino acid (2, 0.40 mmol, 2 equiv.), methyleneindolinone (3, 0.2mmol, 1 equiv.) and MeOH (0.2 mL or 1 mL) were well mixed and stirred at 30C. Once the reaction was completed (monitored by TLC), the resulting residue was purified by flash column chromatography on silica gel to yield the corresponding product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In methanol; at 30℃; for 28h; | General procedure: Isatin (1, 0.20mmol, 1 equiv.), amino acid (2, 0.40 mmol, 2 equiv.), methyleneindolinone (3, 0.2mmol, 1 equiv.) and MeOH (0.2 mL or 1 mL) were well mixed and stirred at 30C. Once the reaction was completed (monitored by TLC), the resulting residue was purified by flash column chromatography on silica gel to yield the corresponding product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In dimethyl sulfoxide; at 28℃; for 72h;Inert atmosphere; | General procedure: In an oven and vacuum-dried flask, N-benzylisatin 1a (0.15 mmol), phenylalanine 2a(0.23 mmol) and (E)-beta-benzylidene-alpha-indanone 3a (0.18 mmol) were taken in 0.5mL ofdry DMSO under argon and the reaction mixture was stirred at 28 C. After completion of the reaction (monitored by TLC), the reaction mixture was poured into 5mL of icecold water and extracted with ethyl acetate (310 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and evaporated. The residue was purified by column chromatography on silica using hexane/EtOAc as eluent to give 4aaa. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; C21H21N4O3(1+)*Cl(1-); N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 10℃; for 24h;Schlenk technique; | General procedure: The substituent R1 is H, R2 is H, and R3 is Bn. The preparation method and conditions are the same as those of the general example I; Weigh 0.15 mmol (23.73 mg) of indole-2-carbaldehyde 1, respectively0.1mmol (21.86mg) indole-2,3-dione 2,0.05 mmol (2.1 mg) of azacyclocarbene catalyst E and 0.17 mmol (69.5 mg) of oxidant DQ were added to a 10 mL Schlenk reaction tube equipped with a magnetic stir bar, 1 mL of solvent tetrahydrofuran THF was added, followed by 0.15 mmol (25 muL) of base N N-diisopropylethylamine DIEA, gently shake the reaction wall to make it fully mixed. Cap the bottle and place in a 10 C isopropanol water bath to stir the reaction for 24h. After the reaction was monitored by TLC, 1 mL of 1N hydrochloric acid was added to the reaction tube, and the mixture was stirred at room temperature for 5 minutes. The organic layer was extracted with ethyl acetate, spin-dried, a small amount of dichloromethane was fully dissolved, and the sample was wet-loaded. The depolarized polar petroleum ether: ethyl acetate = 10: 1 was used to obtain the target compound I1, and the corresponding yield was calculated after weighing. The characterization method was the same as that of the general example I. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With 1,4-diaza-bicyclo[2.2.2]octane; copper(II) tungstate In water at 60℃; Green chemistry; | General procedure for the preparation of 3-hydroxy-3-(phenylethynyl)indolin-2-ones (3a-3u) General procedure: To a mixture of isatin (1 equiv.) and phenyl acetylene (1.2 equiv.) in water (3 mL), CuWO4 (10 mol%) and DABCO (40 mol%) were added at room temperature and the mixture was heated at 60 °C for 2 to 5 h. After completion of reaction (monitoring by TLC) mixture was cooled to room temperature and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography to give 3-hydroxy-3-(phenylethynyl)indolin-2-ones (3a-3u). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: beta-Cyclodextrin (30 mol %), isatoic anhydride (1.0 mol eq.) and substituted isatin (1.0 mol eq.), were mixed in 8 mL water followed by stirring for 0.5 h at room temperature. Then primary amine (1.0 mol eq.) was added and reaction mixture was stirred vigorously upto disappearance of reactants on TLC (monitored by silica TLC). After completion reaction mixture was extracted by ethyl acetate and evaporated under reduced pressure. Solid residue was further crystallized by methanol and filtrate was kept for catalyst recovery. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: beta-Cyclodextrin (30 mol %), isatoic anhydride (1.0 mol eq.) and substituted isatin (1.0 mol eq.), were mixed in 8 mL water followed by stirring for 0.5 h at room temperature. Then primary amine (1.0 mol eq.) was added and reaction mixture was stirred vigorously upto disappearance of reactants on TLC (monitored by silica TLC). After completion reaction mixture was extracted by ethyl acetate and evaporated under reduced pressure. Solid residue was further crystallized by methanol and filtrate was kept for catalyst recovery. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With acetic acid In ethanol for 2h; Reflux; | 3.1.2. General Procedure for Synthesis of the Target Bis-indoles (7a-f and 9a-h), and 11 General procedure: To a hot stirred solution of key intermediate 1H-indole-2-carbohydrazide 5 (0.18 gm, 1 mmoL) inabsolute ethyl alcohol (7 mL) and glacial acetic acid (catalytic amount), the appropriate N-unsubstituted1H-indole-2,3-dione 6a-f, N-substituted 1H-indole-2,3-dione 8a-h, or 1-tetralone 10 (1 mmoL) wasadded. The resulting mixture was refluxed for 2 hours, and then the formed solid was filtered owhile hot, washed with cold isopropyl alcohol, dried and recrystallized from DMF to aord targetbis-indoles (7a-f and 9a-h), and 11, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With acetic acid for 3h; Reflux; | 3.1.3. Synthesis of Final Compounds 6a-i, 9a-f, and 11a,b General procedure: A solution of indole-2-carbohydrazide 4 (210 mg, 1.2 mmol) in glacial acetic acid (15 mL) was treated with the appropriate isatin derivative 5a-i and 8a-f (1.2 mmol), or ketones 10a and 10b (1.2 mmol). The resulting reaction mixture was refluxed for four hours then cooled to r.t. The obtained precipitate was collected by filtration and dried to get a powder that was recrystallized from glacial acetic acid to furnish the titled conjugates 6a-i, 9a-f, and 11a,b. |
Tags: 1217-89-6 synthesis path| 1217-89-6 SDS| 1217-89-6 COA| 1217-89-6 purity| 1217-89-6 application| 1217-89-6 NMR| 1217-89-6 COA| 1217-89-6 structure
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