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CAS No. : | 608-05-9 | MDL No. : | MFCD00005721 |
Formula : | C9H7NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VAJCSPZKMVQIAP-UHFFFAOYSA-N |
M.W : | 161.16 | Pubchem ID : | 11840 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.12 |
TPSA : | 46.17 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.44 cm/s |
Log Po/w (iLOGP) : | 1.03 |
Log Po/w (XLOGP3) : | 1.19 |
Log Po/w (WLOGP) : | 0.56 |
Log Po/w (MLOGP) : | 0.49 |
Log Po/w (SILICOS-IT) : | 1.98 |
Consensus Log Po/w : | 1.05 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.96 |
Solubility : | 1.77 mg/ml ; 0.011 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.76 |
Solubility : | 2.83 mg/ml ; 0.0176 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.15 |
Solubility : | 0.113 mg/ml ; 0.000701 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.5 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | 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 |
---|---|---|
95% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 2h; | The 5 - methyl indole - 2, 3 - dione (161 mg, 1 mmol) suspended in (10 ml) in methylene chloride, in the 0 C in batches under the adding meta-chloroperoxybenzoic acid (344 mg, 2 mmol), at room temperature stirring 2 hours, filter the reaction forming a solid white, ethyl acetate (10 ml) washing 3 times, to obtain white solid (170 mg, 95%) is 6 - methyl - 2H - benzo [d] [1, 3] oxazine - 2, 4 (1 H) - dione (compound 11). |
90% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 4h; | 5Methylisatin 1 (1000 mg, 6.2 mmol) was suspended i n dry dichloromethane (20 mL) in a38 mL tube to which 85% meta chloroperbenzonic acid (2522.8 mg, 14.6 mmol) was added in afew portions at 0 . The mixtu re was then stirred for 4 h at room temperature. The reaction wasfollowed by thin layer chromatograp hy TLC DCM:MeOH = 4 0 :1 , R f = 0.4 )). When the reactionwas complete d, the sample was filtered and washed wi th ethyl acetate (3 × 5 mL) and dried invacuo for 24 h to yield the product in the form of an orange yellow solid (992 mg, 90%). Theanalytical dat a can be found in the SI of t he literature. 1 |
76.3% | With sulfuric acid; dihydrogen peroxide; acetic anhydride; acetic acid; at 70℃; for 4h; | 1) Synthesis of 5-methylisatoic anhydride 6 Acetic acid (1 mL) and concentrated sulfuric acid (0.05 mL) were added to reaction flask, 5-methylindolequinone (161 mg, 1 mmol) was added in batches under stirring, then the mixture of acetic anhydride (0.2 ml ) and 30% hydrogen peroxide (0.23 ml ) was started to add, the reaction solution was heated to 70 C. for 4 h. After TLC monitored that the reaction was completed, the reaction mixture was cooled and suction filtered, the filter cake was successively washed with water, 5% sodium bicarbonate solution and water, the obtained solid was dried under vacuum to give orange-yellow solid 6 135 mg, yield 76.3%. |
71% | With acetic acid; 3-chloro-benzenecarboperoxoic acid; at 20℃; for 4h; | General procedure: To the magnetically stirred solution of the 5-bromoisatin (1)(0.22 g, 1 mmol) in HOAc (2 mL) was added of mCPBA (2.5 g,1.5 mmol, 1.5 equiv) and the resultant mixture was stirred magnetically for another 4 h (TLC). The crude reaction mixture was filtered and washed with aq NaHCO3 to afford 2a as light red solid (0.21 g, 87%). |
65% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 2h; | [0121] Compound 2a (500 mg, 3 mmol) was suspended in 10 ml of dry dichloromethane, afier which metachioroper4oxybenzoic acid (1.3 g, 6 mmol, 75%) was added batchwise at 0 C. TLC indicated that the reaction was complete afier stirring the mixture for 2 hours at room temperature, after which, the white solid produced in the reaction was filtered off and three washes were performed with 10 ml ethyl acetate to obtain Compound 3a (350 mg,65%) |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 4h; | The 1000.0mg (6.213mmol) 5-methylisatin 1 was suspended in 20mL of dry dichloromethane,2293.5 mg (12.43 mmol) of m-chloroperoxybenzoic acid was added at 0 C.Stir at room temperature for 4 hours;After the TLC detection reaction is completed,The reaction mixture was filtered to give an orange solid.To give 5-methylisatoic anhydride 2; | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 4h; | Please refer to the above formula.1000.0 mg (6.213 mmol) of 5-methyl ruthenium 1 was suspended in 20 mL of dry dichloromethane.2522.8 mg (14.62 mmol) of m-chloroperoxybenzoic acid was added at 0 C, and stirred at room temperature for 4 hours;After the completion of the TLC reaction, the orange solid obtained was filtered and washed with ethyl acetate (5 mL, 3).Obtaining 5-methyl isatoic anhydride 2; | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 4h; | 1000.0 mg (6.213 mmol) of 5-methyl ruthenium 1 was suspended in 20 mL of dry dichloromethane.2293.5 mg (12.43 mmol) of m-chloroperoxybenzoic acid was added at 0 C.Stir at room temperature for 4 hours;After the TLC detection reaction is completed,The orange solid obtained by filtering the reaction solution,Wash with (5 mL x 3) ethyl acetate.Obtaining 5-methyl isonianic anhydride | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 1000.0 mg (6.213 mmol) of 5-methyl isatin 1 was suspended in 20 mL of dry dichloromethane, 2293.5 mg (12.43 mmol) of m-chloroperoxybenzoic acid was added at 0 C, and stirred at room temperature for 2 to 4 Hours; after the reaction was detected by TLC, the orange solid obtained by filtering the reaction solution was washed with (5 mL x 3) ethyl acetate to obtain 5-methyl isatoic anhydride 2; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With titanium tetrachloride; zinc; In tetrahydrofuran; at 20℃; for 0.166667h;Inert atmosphere; | General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4. |
50% | A stirred solution of 5-methyl isatin (0.1 mol) in hydrazine hydrate (60 ml) was heated to 140C for 4 h. The reaction mixture was cooled to room temperature, poured into 300 ml of ice water, and acidified to pH 2 with 10% hydrochloric acid. After standing at room temperature for one night the precipitate was collected by vacuum filtration, washed with water, and dried under vacuum (50% yield). | |
47% | With hydrazine hydrate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; | 5-Methyl-2-oxindole 5-Methylisatin (15.0 g) and 60 mL of hydrazine hydrate were heated at 140 to 160 C. for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed no starting material remaining. The reaction mixture was cooled to room temperature, poured into 300 mL of ice water and acidified to pH 2 with 6N hydrochloric acid. After standing at room temperature for 2 days the precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 6.5 g (47% yield) of 5-methyl-2-oxindole. |
47% | With hydrazine hydrate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; | EXAMPLE 9 3-[4-Methyl-5-(5-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrol-3-yl]-propionic acid 5-Methylisatin (15.0 g) and 60 mL hydrazine hydrate were heated at 140-160 C. for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed no starting material remaining. The reaction mixture was cooled to room temperature, poured into 300 mL of ice water and acidified to pH 2 with 6 N hydrochloric acid. After standing at room temperature for 2 days the precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 6.5 g (47% yield) of 5-methyl-2-oxindole. 1H-NMR (360 MHz, DMSO-d6): delta 10.20 (s, br, 1 H, NH-1), 6.99 (s, 1 H, H-4), 6.94 (d, J=8.11 Hz, 1 H, H-6), 6.68 (d, J=8.11 Hz, 1 H, H-7), 3.39 (s, 2 H, CH2-3), and 2.22 (s, 3 H, CH3-5). |
47% | With hydrazine hydrate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; | 5-Methyl-2-oxindole 5-Methylisatin (15.0 g) and 60 mL of hydrazine hydrate were heated at 140 to 160 C. for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed no starting material remaining. The reaction mixture was cooled to room temperature, poured into 300 mL of ice water and acidified to pH 2 with 6N hydrochloric acid. After standing at room temperature for 2 days the precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 6.5 g (47% yield) of 5-methyl-2-oxindole. |
47% | With hydrazine hydrate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; | 5-Methyl-2-oxindole 5-Methylisatin (15.0 g) and 60 mL of hydrazine hydrate were heated at 140 to 160 C. for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed no starting material remaining. The reaction mixture was cooled to room temperature, poured into 300 mL of ice water and acidified to pH 2 with 6 N hydrochloric acid. After standing at room temperature for 2 days the precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 6.5 g (47% yield) of 5-methyl-2-oxindole. |
47% | With hydrazine; In water; at 140 - 160℃; for 4h;Heating / reflux; | 5-Methyl-2-oxindole 5-Methylisatin (15.0 g) and 60 ML of hydrazine hydrate were heated at 140 to 160 C. for 4 hours.. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed no starting material remaining.. The reaction mixture was cooled to room temperature, poured into 300 ML of ice water and acidified to PH 2 with 6N hydrochloric acid.. After standing at room temperature for 2 days the precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 6.5 g (47% yield) of 5-methyl-2-oxindole. |
47% | With hydrazine; at 140 - 160℃; for 4h; | 5-Methyl-2-oxindole 5-Methylisatin (15.0 g) and 60 mL of hydrazine hydrate were heated at 140 to 160 C. for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed no starting material remaining. The reaction mixture was cooled to room temperature, poured into 300 mL of ice water and acidified to pH 2 with 6N hydrochloric acid. After standing at room temperature for 2 days the precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 6.5 g (47% yield) of 5-methyl-2-oxindole. |
With hydrazine hydrate; potassium hydroxide; In ethylene glycol; at 100℃; for 1h; | General procedure: A mixture of substituted isatin (12.3 mmol), hydrazine hydrate (368 mmol), potassium hydroxide (245 mmol), and ethylene glycol (242 mmol) were heated at 100 C for 1 h. The reaction mixture was cooled on ice bath and acidified using concd HCl (drop wise addition) along with vigorous stirring. The precipitated product was vacuum filtered and washed with hexanes to give substituted indolin-2-ones in 90-95% yield. | |
With hydrazine hydrate; potassium hydroxide; In ethylene glycol; at 110 - 130℃; | General procedure: To a mixture of isatin (6a-e, 1.0 g) and hydrazine-hydrate (5 mL,~30 mmol) in ethylene glycol, potassium hydroxide (10 equiv.) was added and the resulting reaction mixturewas stirred at 110-130 C for 2-3 h (reaction monitored by TLC). The reaction mixture wascooled to room temperature, poured into ice-cold water (50 mL), acidified to pH 2 with 6N hydrochloric acid and extracted with ethylacetate (3 30 mL). The organic extracts were combined, washed with brine (15 mL), dried over sodium sulfate and concentrated in vacuo. The obtained residue was purified by column chromatography using ethyl acetate-hexane as eluents to furnish 7a-e in moderate yields. | |
With hydrazine hydrate; potassium hydroxide; In ethylene glycol; at 110 - 130℃; | General procedure: To a mixture of isatin (7a-e, 1.0 g) and hydrazine-hydrate (5 mL, ~30 mmol) in ethylene glycol,potassium hydroxide (10 equiv.) was added and the resulting reaction mixture was stirred at110-130 C for 2-3 h (monitored by TLC). The reaction mixture was cooled to roomtemperature, poured into ice-cold water (50 mL), acidified to pH 2 with 6N hydrochloric acidand extracted with ethyl acetate (3 x 30 mL). The organic extracts were combined, washed withbrine (15 mL), dried over sodium sulfate and concentrated in vacuo. The obtained residue waspurified by column chromatography using ethyl acetate-hexane as eluents to furnish 8a-e inmoderate yields. | |
With hydrazine hydrate; at 130℃; | General procedure: Substituted isatin (10 mmol) was dissolved in hydrazine hydrate (98%, 10 mL, 32.5 mmol) and refluxed for 15-30 min (130 C). The reaction mixture was then poured into cold water, extracted withethyl acetate. The organic layer was then dried over sodium sulfate. Evaporation of the solvent and recrystallization from hexane/ethylacetate provided the substituted oxindole. | |
With titanium tetrachloride; zinc; In tetrahydrofuran; at 20℃; for 0.0833333h;Inert atmosphere; | General procedure: TiCl4 (0.7 mL, 6 mmol) wasadded to a stirred suspension of Zn powder (0.78 g, 12 mmol) infreshly distilled anhydrous THF (15 mL) at room temperature (r.t.)under a dry N2 atmosphere. After completion of the addition, themixture was refluxed for 2 h. The suspension of the low-valent titaniumreagent formed was cooled to r.t. A solution of isatin derivatives(2 mmol) in THF (10 mL)was added dropwise. The mixturewas stirred at room temperature for about 5 min under N2. Afterthis period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture wasquenched with 5% HCl (15 mL) and extracted with CH2Cl2(3 x 50 mL). The combined extracts were washed with water (350 mL) and dried over anhydrous Na2SO4. After evaporation of thesolvent under reduced pressure, the crude product was purified bycolumn chromatography (petroleum ether/EtOAc = 5:1) to give thepure products 9a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With acetic acid microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; oxygen; In acetonitrile; at 20℃; for 18h; | General procedure: An oven-dried flask was charged with stir bar, oxindole (0.5 mmol), PIDA (0.25 mmol) in dry acetonitrile (4.0 mL). Then to the reaction mixture TEMPO (0.5 mmol) was added in presence of air and the mixture was stirred at room temperature until complete conversion takes place as indicated by TLC analysis. The resulting reaction mixture was extracted with ethyl acetate (3 10 mL). The combined organics were dried with Na2SO4 and dried under vacuum to afford crude solid. Then the crude product was purified by column chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In tetrahydrofuran; ethanol; water; at 85℃; for 2.5h;Reflux; | General procedure: A solution of the appropriate phenacylamine hydrochloride (10mmol) in a mixture of water (18mL), ethanol (18mL), and THF (8mL), was added to a solution of the appropriate isatin (8mmol) and sodium hydroxide (57mmol) in water (8mL) at 85C, in a dropwise manner over 2h. The resulting mixture was heated under reflux for additional 30min. The reaction mixture was concentrated under reduced pressure and filtered through Celite. The filtrate was acidified with acetic acid and the precipitate obtained was filtered, washed with water, and dried. The crude product was purified by recrystallization from ethanol/ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With picolinaldehyde oxime-grafted SBA-15 supported zinc complex; In water; for 0.5h;Reflux; Green chemistry; | General procedure: A mixture of isatin 1 (1 mmol), 1,3-indandion 2 (1 mmol), aminouracil 3 (1 mmol) andSBA-oxime-Zn (0.1 g) was heated in refluxing water(5 mL) for appropriate time (Table 1). The reactionwas monitored by TLC (n-hexane-ethyl acetate 1:1),and after completion of the reaction, the reactionmixture was filtered for separation of solid productand catalyst from water. The remaining solid waswashed with ethanol (2×10 mL) for separation ofthe product from the catalyst. Finally, the productwas purified by recrystallization in hot EtOH. The desired pure products were characterized bycomparison of their melting point data with literature.All the products are known compoundsand their melting points are compared with reportedvalues [14]. Some selected samples were alsocharacterized by IR and NMR spectroscopic data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Example 84 4-Methyl-2-(5-methyl-2,3-dioxo-2,3-dihydro-indol-1-yl)-pentanoic acid pyrazin-2-ylamide A stirred suspension of sodium hydride (60% dispersion in oil, 297 mg) in N,N-dimethylformamide (15 mL) at 0 C. was treated with a solution of 5-methyl-1H-indole-2,3-dione (1.0 g) in N,N-dimethylformamide. The reaction mixture was stirred for 30 min at 0 C. and then 2-bromo-4-methyl-pentanoic acid methyl ester (prepared as in Example 9, 1.56 g) was added and it was stirred for 1 h at 0 C. It was then slowly allowed to warm to room temperature and stirred for another 3 h at room temperature. After this time, the reaction mixture was diluted with water and extracted with chloroform. The organic layers were combined and dried over sodium sulfate, filtered and the filterate concentrated in vacuo. The crude material was purified by column chromatography (silica gel, 5% ethyl acetate/hexanes) to afford 4-methyl-2-(5-methyl-2,3-dioxo-2,3-dihydro-indol-1-yl)-pentanoic acid methyl ester (1.0 g, 56%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; | General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In methanol at 100℃; for 0.25h; Microwave irradiation; Green chemistry; stereoselective reaction; | |
for 0.25h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dimethylsulfoxide-d6; at 20℃; | General procedure: To a mixture of 5-chloroisatin (182 mg, 1.0 mmol) and N-carboxyethylrhodanine (205 mg, 1.0 mmol) was added DMSO-d6 (3.0 mL). The reaction was followed by proton NMR until the disappearance of the starting material. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With L-proline; In ethanol; water; at 25℃; for 0.833333h;Sonication; | General procedure: Substituted phenylhydrazine (1mmol), dialkyl acetylenedicarboxylate (1mmol) and water/ethanol (v/v, 1:1, 5mL) were mixed and maintained under ultrasonic irradiation (40kHz, normal power 250W) at room temperature for 5min. Substituted isatin (1mmol), malononitrile (1mmol), and l-proline (10mol%) were added to the reaction system and continuously irradiated for the appropriate time (Table 2) at the same temperature and sonication frequency. The progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was filtered off and purified by recrystallization from ethanol to give the desired product 5 in high purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water at 50℃; for 1h; Sonication; Combinatorial reaction / High throughput screening (HTS); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water at 50℃; for 1h; Sonication; Combinatorial reaction / High throughput screening (HTS); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In ethylene glycol; at 120℃; for 0.2h;Microwave irradiation; | General procedure: General procedure for the synthesis of 4: A solution of isatin 1 (1mmol), malononitrile 2 (1mmol), <strong>[100643-27-4]2,6-diaminopyrimidin-4-one</strong> or 6-aminopyrimidine-2,4-dione 3(1mmol) in 2 mL glycol was put in a 10 mL EmrysTM reactionvial, and capped. The mixture was pre-stirred for 2 minand irradiated at 250 W and at 120 C for given minutes. Upon completion, monitored by TLC, the reaction mixture was cooled to room temperature, filtered and washed with small amount of cold EtOH to give the crude product. The pure product was further purified by recrystallization from DMF solvent. This procedure was followed for the synthesis of all the spirooxindoles (4a-4i). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With acetic acid; In ethanol;Reflux; | General procedure: 6-Fluoro-2-(2-(5-(un)substituted-2-oxoindolin-3-ylidene)hydrazino)benzothiazoles 5a-c. General Procedure C. A mixture of compound 2 (0.183 g, 0.001 mol), the appropriate isatin (0.001 mol) and glacial acetic acid (0.1 mL) in ethanol (20 mL) was heated at reflux temperature for 4-6 h. The precipitated yellow to orange solid was collected by filtration, washed with ethanol, dried and crystallized from methanol to yield compounds 5a-c. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With cobalt(III) meso-5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin chloride; In ethanol; water; at 20℃; for 6h;Green chemistry; | General procedure: In a 50 mL round bottom flask, CoTCPP (3 mol %) was dissolved in water (15 ml) at room temperature. Isatin 2 (1 mmol) and isatoic anhydride 1 (1mmol) were added. Due to the partial solubility of somestarting materials in water, a mixed solvent systemof water and ethanol (v/v) (5/1) was used. The reaction mixture was stirredat room temperature for the appropriate time. Thereaction mixture was extracted with ethyl acetate and the organic layer wasdried over Na2SO4 and concentrated in vacuo. The resulting crudeproduct, was purified by recrystallization from aqueous ethanol to give tryptanthrin derivatives 3a-p. All the products are reportedin the literature16,17 and the data of the products are given in thesupporting information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With cobalt(III) meso-5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin chloride; In ethanol; water; at 20℃; for 4h;Green chemistry; | General procedure: In a 50 mL round bottom flask, CoTCPP (3 mol %) was dissolved in water (15 ml) at room temperature. Isatin 2 (1 mmol) and isatoic anhydride 1 (1mmol) were added. Due to the partial solubility of somestarting materials in water, a mixed solvent systemof water and ethanol (v/v) (5/1) was used. The reaction mixture was stirredat room temperature for the appropriate time. Thereaction mixture was extracted with ethyl acetate and the organic layer wasdried over Na2SO4 and concentrated in vacuo. The resulting crudeproduct, was purified by recrystallization from aqueous ethanol to give tryptanthrin derivatives 3a-p. All the products are reportedin the literature16,17 and the data of the products are given in thesupporting information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With cobalt(III) meso-5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin chloride; In ethanol; water; at 20℃; for 6h;Green chemistry; | General procedure: In a 50 mL round bottom flask, CoTCPP (3 mol %) was dissolved in water (15 ml) at room temperature. Isatin 2 (1 mmol) and isatoic anhydride 1 (1mmol) were added. Due to the partial solubility of somestarting materials in water, a mixed solvent systemof water and ethanol (v/v) (5/1) was used. The reaction mixture was stirredat room temperature for the appropriate time. Thereaction mixture was extracted with ethyl acetate and the organic layer wasdried over Na2SO4 and concentrated in vacuo. The resulting crudeproduct, was purified by recrystallization from aqueous ethanol to give tryptanthrin derivatives 3a-p. All the products are reportedin the literature16,17 and the data of the products are given in thesupporting information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With toluene-4-sulfonic acid In toluene for 16h; Reflux; | Typical experimental procedure for the synthesis of compounds 5 General procedure: To a mixture of isatin (147.0 mg, 1.0 mmol), 5,5-dimethylcyclo-hexane-1,3-dione (140.0 mg, 1.0 mmol) and 1-phenyl-3-(triuoromethyl)-1H-pyrazol-5(4H)-one (228.0 mg, 1.0 mmol) in toluene (10.0 mL) was added p-TSA (258.0 mg, 1.5 mmol). The resulting mixture was stirred in reflux until the reaction was completed (16 h, monitored by TLC). The solvent was removed under reduced pressure and then the residue was puried by column chromatography on silica gel using petroleum/ethyl acetate = 5:1 (v/v) as eluent to afford 5a (398.0 mg, 83% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With toluene-4-sulfonic acid In toluene for 16h; Reflux; | Typical experimental procedure for the synthesis of compounds 5 General procedure: To a mixture of isatin (147.0 mg, 1.0 mmol), 5,5-dimethylcyclo-hexane-1,3-dione (140.0 mg, 1.0 mmol) and 1-phenyl-3-(triuoromethyl)-1H-pyrazol-5(4H)-one (228.0 mg, 1.0 mmol) in toluene (10.0 mL) was added p-TSA (258.0 mg, 1.5 mmol). The resulting mixture was stirred in reflux until the reaction was completed (16 h, monitored by TLC). The solvent was removed under reduced pressure and then the residue was puried by column chromatography on silica gel using petroleum/ethyl acetate = 5:1 (v/v) as eluent to afford 5a (398.0 mg, 83% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With copper(l) iodide In ethylene glycol at 80℃; for 0.25h; | Synthesis of products; general procedure General procedure: A mixture of the isatin (1.0 mmol), 2-amino-2-thiazoline (1.0 mmol) andmalononitrile or ethyl cyanoacetate (1 mmol) in ethylene glycol (2 mL) witha catalytic amount of CuI (5 mol%) was stirred using a magnetic stirrer at80 °C for 15 min. After completion of the reaction (monitored by TLC),the reaction mixture was cooled, poured into H2O and extracted withEtOAc (3 × 15 mL). The organic layer was separated, dried with Na2SO4and concentrated to afford the corresponding spirooxindole 4, which wasfiltered off and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With copper(l) iodide In ethylene glycol at 80℃; for 0.25h; | Synthesis of products; general procedure General procedure: A mixture of the isatin (1.0 mmol), 2-amino-2-thiazoline (1.0 mmol) andmalononitrile or ethyl cyanoacetate (1 mmol) in ethylene glycol (2 mL) witha catalytic amount of CuI (5 mol%) was stirred using a magnetic stirrer at80 °C for 15 min. After completion of the reaction (monitored by TLC),the reaction mixture was cooled, poured into H2O and extracted withEtOAc (3 × 15 mL). The organic layer was separated, dried with Na2SO4and concentrated to afford the corresponding spirooxindole 4, which wasfiltered off and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; In toluene; for 24h;Reflux; | a. PREPARATION OF 5-(2-(2H-TETRAZOL-5-YL)ETHYL)-8-METHYL-5H- [l,2,5]OXADIAZOLO[3',4':5,6]PYRAZINO[2,3-B]lNDOLE (COMPOUND 39) [00308] To a solution of 39C (0.020 g, 0.072 mmol) in toulene (10 mL) was added nBu3SnN3 (0.12 g, 0.36 mmol). The resulting mixture was heated to reflux for 48 h. Then, it was cooled to room temperature, and the pH value was adjusted to 4-5 with HCl (1M), diluted with ethyl acetate (60 mL), and the organic phase was washed with brine (20 mLx 2), then dried over Na2SC>4 and concentrated. The residue was purified by column chromatography (silica gel, CH2C12 : MeOH = 10: 1 - 5: 1) to afford 39 (13.00 mg, 57% yield) as orange solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With acetic acid; In water; at 90℃; for 6h;Green chemistry; | General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With acetic acid; In water; at 90℃; for 6h;Green chemistry; | General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In water; for 1h;Reflux; | To further broaden the catalytic efficiency of the Fe3O4-MnO2 NCs, MnO2, and Fe3O4, a reaction of isatin (1a), and 2,3-lutidine (2a) was refluxed in water (10mL) in the presence of 2mol.% of the Fe3O4-MnO2 NCs (6.37mg), MnO2 (1.75mg), or Fe3O4 (4.63mg), as shown in Scheme 2 . The expected product 3a was obtained in high yield (91%). The product 3a was determined by an analysis of its spectral data and compared with the reported data [43]. To synthesize a variety of azaarene-substituted 3-hydroxy-2-oxindole derivatives, the reactions of substituted isatins bearing either electron-donating or electron-withdrawing groups and 2,3-lutidine (2a), 2,6-lutidine (2b), or 2-picoline (2c) gave the desired products 3b-3e in 80-90% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With acetic acid; In ethanol; at 100℃; for 0.25h;Microwave irradiation; | General procedure: <strong>[2231-57-4]<strong>[2231-57-4]Thiocarbohydrazid</strong>e</strong> (1) (1.06 g, 0.01 mol), isatin derivatives 2a,b(0.01 mol) and glacial acetic acid (0.1 mL) were heated in absolute ethanol (10 mL) under microwave irradiation (50 W) at 100 C for15 min. The precipitated solid upon cooling was filtered, dried and crystallized from ethanol to give compounds 3a,b. 6.1.1.1 3-Amino-1-[(5-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)amino]thiourea (3a) Yield 86%, m.p. 189-191 C. 1H NMR (DMSO-d6, delta ppm): 2.25 (s, 3H, CH3), 5.25 (s, 2H, NH2), 6.75-7.65 (m, 3H, Ar-H), 10.70 (s, 1H, NH), 11.10 (s, 1H, NH), 12.40 (s, 1H, NH). 13C NMR (DMSO-d6, delta ppm): 21.1, 120.5, 121.8, 131.7, 131.8, 132.9, 136.2, 140.3, 163.2, 180.7. Anal. C10H11N5OS (249.29) (C, H, N). |
With acetic acid; In ethanol; at 100℃; for 0.25h;Microwave irradiation; | A mixture of thiocarbohydrazide (1) (1.06 g, 0.01 mol), 5-methylisatin (2) (1.612 g, 0.01 mol) and glacial acetic acid (0.1 mL) in ethanol (10 mL) was heated under microwave irradiation (50 W) at 100 C for 15 min. The precipitated solid upon cooling was filtered, dried and crystallized from ethanol to give compound 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With iodine pentoxide; In dimethyl sulfoxide; at 80℃; | General procedure: Indoles 1 (0.5 mmol), DMSO (3mL) and I2O5 (1 mmol) were added into a flask and vigorously stirred at 80oC under air. The reaction was stopped until indoles were completely consumed as monitored by TLC analysis. After the completion of reaction, saturated Na2S2O3 solution (20 mL) was added to the mixture. The mixture was extracted with EtOAc (3×20 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. Then, the crude product was purified by column chromatography on silica gel using ethyl acetate and petroleum ether as the eluent to give the products 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With acetic acid; In ethanol; at 80℃; for 2.0h; | General procedure: A mixture of 4-hydroxy-2H-chromen-2-one (1a, 1 mmol), isatin (2a, 1 mmol) and 1H-indazole-3-amine (3a, 1 mmol) and acetic acid (20 mol %) in EtOH (5 ml) was stirred on a magnetic stirrer at 80 C for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with ethanol to afford the product 4a in excellent yield (91%). Compounds 4b-4r were also synthesized by adopting same procedure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With acetic acid; In ethanol; at 80℃; for 2h; | General procedure: A mixture of 4-hydroxy-2H-chromen-2-one (1a, 1 mmol), isatin (2a, 1 mmol) and 1H-indazole-3-amine (3a, 1 mmol) and acetic acid (20 mol %) in EtOH (5 ml) was stirred on a magnetic stirrer at 80 C for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with ethanol to afford the product 4a in excellent yield (91%). Compounds 4b-4r were also synthesized by adopting same procedure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With toluene-4-sulfonic acid; In acetonitrile; at 80℃; for 5h; | General procedure: The mixture of substituted isatins 1 (1 mmol), phthalic anhydride or succinic anhydride 2 (1 mmol), 1,3-dimethylurea (1,3-diethylurea) 3 (1.5 mmol), p-TSA?H2O (0.2 mmol), and CH3CN (3 mL) was put in a 25 mL flask and reacted under 80 C (monitored by TLC) about 5 h. After completion, the reaction the mixture was cooled to room temperature and the precipitate was obtained by filtration. Compound 4 was purified by recrystallization from EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With acetic acid; In ethanol; for 10h;Reflux; | 5-methyl isatin (3c, 0.319 g, 2.00 mmol),[2-(4-aminophenoxy)ethyl]morpholine (4a, 0.444 g, 2.00 mmol)Added to 50mL eggplant flask,Then add anhydrous ethanol (10.0 mL),Stirring at room temperature by adding glacial acetic acid (1-2 drops),Heated to reflux for 10 hours,TLC test reaction end, until the system cooled to room temperature,A small amount of dark red solid precipitation, adding appropriate amount of water,A large number of solid precipitation, pumping, drying dark red solid,The title compound 5-methyl-3-({4-[2-(morpholin-4-yl)ethoxy]phenyl}imino)-2,3-dihydro-1H-indol-2-one(T9, 0.327 g, 45%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: A mixture of 1.0 mmol of isatin, 1.0 mmol of malononitrile and 1 mol% of chloroauric acid in 15 mL of water was stirred at room temperature for 15 min. To this mixture was added 1.2 mmol of <strong>[60-27-5]creatinine</strong> and the resulting suspension was heated to reflux for 30 min and then cooled to room temperature. The precipitated product was filtered and washed with copious amount of water and then with methanol and ethyl acetate. The obtained product was thoroughly dried under vacuum to afford the crude product. The crude product was purified by column chromatography using hexane/EtOAc eluent system to afford the inseparable diastereoisomeric mixture of 3a-3e. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With sodium hydroxide; In water; for 4h;Reflux; | General procedure: A mixture of <strong>[88-03-9]methylphloroglucinol</strong> (MPHG) 1 (0.7 g, 0.005 mol), isatin 2 (0.68 g, 0.0046 mol), and an aqueous solution of sodium hydroxide (0.68 g, 0.017 mol in water (5.5 mL)) was refluxed for 4 h, using a reflux condenser. The resulting mixture was cooled to room temperature, acidified with a 10% solution of hydrochloric acid to pH ? 6-7. A precipitate formed was collected by filtration on a Buchner funnel, washed with water and acetone on the filter, and dried in air to obtain the product (1.21 g, 97%) as a light orange powder, m.p. 270 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | at 60℃; for 0.25h;Microwave irradiation; Green chemistry; | General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; | General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: 2,6 difluorobenzonitrile With hydrazine In ethanol at 80℃; for 0.5h; Green chemistry; Stage #2: 5-methyl-indole-2,3-dione; dimedone With toluene-4-sulfonic acid In ethanol at 80℃; for 4h; Green chemistry; | General procedure for the synthesis of the Synthesis of spiro[indazolo[3,2-b]quinazoline-7,3'-indolines (5). General procedure: To an oven dried round bottom flask charged with a mixture of 2-fluorobenzonitrile (1a, 1 mmol) and hydrazine (2a, 1mmol) in ethanol (3 ml), stirred the reaction mixture at 80 °C, for 30 min. To the reaction mixture isatin (3a, 1 mmol), 5,5-dimethyl-1,3-cyclohexanedione (4a, 1 mmol) and p-TSA (40 mol %) was added and the reaction mixture was further stirred at 80 C for 4 h. The progress of the reaction was monitored by TLC. After completion of the reaction, solid products was filtered under vacuum, air dried, to obtain the analytically pure products. The compounds 5a-5r were also synthesized by adopting this procedure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tert.-butylhydroperoxide; caesium carbonate; at 20 - 30℃; for 4h;Sealed tube; | General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), TBHP (70%, 257 mg, 2.0 mmol), and Cs2CO3 (652 mg, 2.0 mmol) at room temperature, and then solvent CH3OH (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 50 mL). The extract was washed with 30%NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate =10:1) to yield the desired product 4a as a yellow liquid (93% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With ammonium hydroxide; dihydrogen peroxide; In dimethyl sulfoxide; at 20 - 30℃; for 4h;Sealed tube; | General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25%, 421 mg, 3.0 mmol) and H2O2 (30%, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30% NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With 1,7-bis(((pyridin-2-ylmethyl)amino)methyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diol; potassium hydroxide; palladium dichloride; In dimethyl sulfoxide; at 110℃; | isatin(1.0 mmol) was added to a 50 mL dry round bottom flask in turn.O-iodophenylacetonitrile (1.0 mmol), 4-hydroxycoumarin (1.0 mmol),Catalyst 3e (5 mol%), palladium dichloride (5 mol%),KOH (20mol%), DMSO 3mL, mix well, 110 C,Stir the reaction, after the reaction is finished (TLC tracking), add appropriate amount of water,Extract with ethyl acetate, combine the organic phases, and distill off the excess solvent in the system under reduced pressure.The crude product was separated by column chromatography (V petroleum ether: V ethyl acetate = 1:1 gradient elution) to give the title compound 12d, yield 82% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate; In N,N-dimethyl-formamide; at 70℃;Inert atmosphere; | General procedure: General procedure for the synthesis of a1-a6: To a solution of indoline-2,3-diones (10 mmol) in DMF (40 mL) was added K2CO3(15 mmol, 2.073 g) and <strong>[52997-43-0]7-(bromomethyl)pentadecane</strong> (11 mmol,3.358 g) under nitrogen. The mixture was stirred at 70 C and monitoredby TLC. After the reaction completed, water was added, andextracted with EtOAc. The organic layer was combined and dried withMgSO4. After evaporation of the solvent, the residue was purified bycolumn chromatograph (eluent: Petroleum/EtOAc=20:1) to give thetarget compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | 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 |
---|---|---|
69% | With acetic acid for 4h; 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In ethanol for 0.4h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With acetic acid; In ethanol; at 40 - 50℃; | General procedure: For the synthesis of Schiffbase, 1-3 substituted isatin was treated with commercially available different aromatic amines (1:1) in ethanol (30 mL) containing a few drops of glacial acetic acid. The resulting reaction mixture was heated at 40 -50 C for 3-4 h. The progress of the reaction was checked by TLC. After the completion of the reaction, the reaction mixture was cooled at room temperature, concentrated, poured into ice cold water and basified with 2 M NaOH (pH 10) resulting in the formation of a precipitate. The precipitate was filtered, washed with water and dried over CaCl 2 in the vacuum chamber to obtain the crude prod- uct. The product was then purified by column chromatography and finally crystallized using ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With Co3O4 supported hyper cross linked copolymer prepared from N-methylenebisacrylamide and (1-(2-methacryloyloxy)ethyl)-3-vinylimidazolium bromide monomers In water for 0.2h; Sonication; regioselective reaction; | 2.5. General preparation of 3,3'-spirooxindoles General procedure: A mixture of isatin (1 mmol), activated methylene (1 mmol),4-hydroxy coumarin or hydantoin/2-thiohydantoin, and proposedcatalyst were sonicated in an ultrasonic bath for appropriate times.The reaction completion was checked by thin layer chromatographytechnique and then the heterogeneous catalyst wasmagnetically separated. As the last step of multicomponent reaction,the separated product was collected and washed with ethylacetate/ hexane mixture (3:7 ratio). All products were characterizedby melting point (m.p.), 1H NMR, 13C NMR, FTIR, andelemental analysis. The spectral data of all compounds areprovided in Supplementary Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With magnetic biochar sulfonic acid In ethanol for 1h; Reflux; | General procedure for synthesis of spiro-pyrazolo[3,4-b]pyridines General procedure: CoFe2O4/BC-SO3 (10 mg) was added to a mixture of isatin (1.0 mmol), 3-oxo-3-phenylpropanenitrile (1.0 mmol), 1H-pyrazol-5-amine (1.0 mmol) in ethanol (2 mL). The reaction mixture was stirred under reflux conditions for the appropriate time. After the completion of the reaction as monitored with TLC, the catalyst was separated by an external magnet and washed with ethanol. The filtrate was cooled to room temperature, and water (2 mL) was added, the product was precipitated and isolated by filtration. |
Tags: 608-05-9 synthesis path| 608-05-9 SDS| 608-05-9 COA| 608-05-9 purity| 608-05-9 application| 608-05-9 NMR| 608-05-9 COA| 608-05-9 structure
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P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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