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CAS No. :26960-68-9 MDL No. :MFCD02315132
Formula : C15H10ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 271.70 Pubchem ID :-
Synonyms :

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* 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.

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[ 26960-68-9 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 17630-76-1 ]
  • [ 100-39-0 ]
  • [ 26960-68-9 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In acetonitrile General procedure for the synthesis of N-benzyl isatins General procedure: Isatin (1mmol), corresponding benzyl bromide (1mmol) and K2CO3 (3mmol) were heated in acetonitrile for 1-2 hours. After completion of the reaction, acetonitrile was removed on rotavopar and the product was extracted using ethylacetate. The organic layer was dried over anhydrous Na2SO4 and concentrated. The product obtained was used for next step without further purification.
98% With potassium carbonate In acetonitrile Heating; 1-benzyl-5-chloroindoline-2,3-dione General procedure: Isatin (1 mmol), corresponding benzyl bromide (1 mmol) andK2CO3 (3 mmol) were heated in acetonitrile for 1e2 h. Aftercompletion of the reaction, acetonitrile was removed on rotavoparand the product was extracted using ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated. Theproduct obtained was used for next step without furtherpurification
94% Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0℃; for 8h; Inert atmosphere;
90% Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;
86% Stage #1: 5-chloroindole 2,3-dione With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 80℃; for 0.166667h; Microwave irradiation; Synthesis of Isatin Derivatives (1b-1f) General procedure: A mixture ofisatin (5mmol) and potassium carbonate (8mmol) in DMF(10 mL) was stirred for 10minutes at roomtemperature. Alkylhalides (6mmol; benzyl bromide for preparation of 1c, 1d,and 1e; CH3I forpreparationof 1b; and1,3-dibromoethane forpreparation of 1f) were added dropwise to the reaction mixtureand then the reaction was microwave irradiated usinga multimode reactor (Synthos 3000, Anton Paar GmbH,Graz, Austria) (1,400W maximum magnetron). The vesselswere heated for 5 minutes at 80∘C and held at the sametemperature for a further 5 minutes (400 W). Cooling wasaccomplished by a fan (5 minutes). The final product wasdried and recrystallized from ethanol. All the spectral datafor the products obtained were in good agreement with thereported data.
86% Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 0℃; for 1h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide; paraffin oil for 1h; Inert atmosphere; General procedure forthe synthesis of N-alkylindolin-2,3-diones General procedure: To a stirring solution of indolin-2,3-dione (2.0g, 13.6 mmol, 1.0 equiv.) in anhydrous DMF, sodium hydride (60% suspension inparaffin oil, 0.65 g, 16.32 mmol, 1.2 equiv.) was slowly added at 0 oCunder inert atmosphere. After 1 h, benzyl bromide (1.78 mL, 14.96 mmol,1.1 equiv.) or prenyl bromide (1.73 mL, 14.96 mmol,1.1 equiv.) or methyl iodide ( 0.93 g, 14.96, 1.1equiv.) was added dropwise. Reaction mixture was stirred for another hour.Completion of the reaction was monitored by TLC. The reaction mixture was thenquenched with aq. NH4Cl, washed with water, extracted into ethylacetate. The ethyl acetate fraction was dried over anhydrous sodiumsulfate. It was evaporated under vacuumto give a solid compound which was purified by column chromatography on silicagel (60-120 mesh) using ethyl acetate-hexane (3:97) mixture as eluent.
85% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;
84% Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; 4.2.1. 1-Benzylisatin 2a General procedure: Isatin (6.14 g, 41.8 mmol) was placed in a 250 mL round bottom flask and dissolved in DMF (80 mL). The bright orange solution was cooled to 0 °C using an ice/water bath. Next, NaH (1.84 g, 46.0 mmol, 60 wt% in mineral oil) was added portionwise forming a deep purple solution. The resulting mixture was stirred until any effervescence had ceased. Then benzyl bromide (6 mL, 50.2 mmol) was added dropwise, and the resulting red-brown mixture was stirred for an additional 1 h at 0 °C. After being quenched by H2O (200 mL), the precipitated crude product was filtered and recrystallized from EtOH to give an orange solid (8.3 g, 84% yield).
83.8% With tetrabutylammonium bromide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; N-substitution isatin derivatives 6j-p: General procedure: In the presence of K2CO3 (1mol) and tetrabutylammonium bromide (1mol), isatin or substituted isatin 6a-i (0.5mol) was reacted with BnBr or CH3I (1mol) in DMF (6L) and the reaction mixture was stirred 12h at room temperature. Intermediates 6j-p were obtained by filtration and purified by recrystallization from acetic acid with high yield (72.7%-85.1%).
78% With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h;
72% Stage #1: 5-chloroindole 2,3-dione With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: benzyl bromide In N,N-dimethyl-formamide for 12h; Synthesis of N-Benzyl Isatins 1g-n with Substituents on the PhenylRing; General Procedure General procedure: To a round-bottomed flask was added isatin (5 mmol, 1 equiv), dimethylformamide(5 mL), and K2CO3 (6 mmol, 1.2 equiv), and thesolution was stirred at r.t. for ten minutes. The solution rapidly turneddark purple. Benzyl bromide, methyl iodide, allyl bromide, propargylbromide, or trityl chloride (5.5 mmol, 1.1 equiv) was added in oneportion. The reaction mixture rapidly changed color. After 12 h, water(10 mL) was added, then the suspension was vacuum filtered, and purifiedby column chromatography on silica gel to afford the product.
66.84% Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: benzyl bromide at 20℃; for 1h; Synthesis of 1-benzyl-5-chloro-isatin 5-Chloro isatin (0.5 g, 0.002 mol) was dissolved in DMF(3 mL) and the solution was cooled to 0 °C. NaH (0.167 g,0.006 mol) was added and the mixture stirred for 15 min at 0°C and then benzyl bromide (0.7 mL, 0.005 mol) was addeddropwise to the reaction mixture and stirred for 1 hour atroom temperature. It was diluted with water and extractedwith EtOAc (3x50 mL). The combined organic phase driedover anhydrous Na2SO4. Evaporation of the solvent gavecrude compounds, which were purified by column chromatography(hexane/ethylacetate 9:1) to give 1b (0.5 g,66.84%, M.p.: 123 °C, MS (ESI): m/z, 272.26 [M+1]+).
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil for 1h; Inert atmosphere;
Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h;
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h;
Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 72h; Synthesis of N-benzyl isatin and N-benzyl-5-chloro isatin General procedure: Isatin and 5-chloro isatin (0.03 mol) was dissolved in DMF (6 ml) and the solution was cooled to 0°C. NaH (0.09 mol) was added and the mixture stirred for 15 min at 0°C and then 45 min at room temperature. Benzyl bromide (0.07 mol) was added dropwise to the rection mixture and stirred for 72h at room temperature. It was diluted with water and extracted with EtOAc (3x50 ml). The combined organic phase was dried over anhydrous Na2SO4. Evaporation of the solvent gave crude compounds, which were purified by column chromatography using hexane: ethyl acetate (9.5:0.5) and following EtOH crystallization.
With potassium carbonate In acetonitrile for 24h; Reflux; Protection of Isatin (6) General procedure: To a mixture of the protecting reagent RBr (0.2 mmol) and K2CO3 (0.138 g) in MeCN (10 mL), isatin (6) was added (0.147 g) at room temperature. After that, the reaction mixture was stirred 24 h at reflux. Then, the solvent was evaporated under vacuum, and the reaction crude was purified by column chromatography (SiO2, Hex:EtOAc 8:2), giving rise to the corresponding product 7.
Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;
With sodium hydride In N,N-dimethyl-formamide at 20℃;
With potassium carbonate In N,N-dimethyl-formamide for 3h; Reflux;
With potassium carbonate In N,N-dimethyl-formamide at 25℃;
With sodium hydride In N,N-dimethyl-formamide Reflux;
With potassium carbonate In acetonitrile Heating; General procedure for the synthesis of N-benzyl isatins General procedure: Isatin (1 mmol), corresponding benzyl bromide (1 mmol) and K2CO3 (3 mmol) were heated in acetonitrile for 1-2 h. After completion of the reaction, solvent was removed under vacuum and the product was extracted using ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated. The product obtained was used for next step without further purification.
With potassium carbonate In acetonitrile for 3h; Reflux;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; 4.1.7 General procedure for synthesis of N-substituted isatins 13a-d General procedure: To a mixture of isatins 12a,c (3mmol) and anhydrous potassium carbonate (1.24g, 9mmol) in dry DMF (15mL), bromomethane 9a or benzyl bromide 9b (6mmol) was added. The mixture was stirred at room temperature for 24h. The reaction mixture was poured into ice water. The formed precipitate was filtered off and washed with water and petroleum ether and recrystallized from ethanol to afford compounds 13a-d [29,30].
With potassium carbonate; potassium iodide for 3h; Reflux; 4.1.3. Synthesis of N-substituted isatin derivatives 4a-f and 8a-l General procedure: Isatin derivatives 1a-c (0.005 mol) were stirred in acetonitrile(20 mL) with (0.007 mol) of the appropriate methyl iodide 2, propyliodide 3 or benzyl bromide 7a-d in the presence of catalytic amountof potassium iodide with (0.010 mol) of dry potassium carbonate atreflux temperature. The reaction was monitored with TLC. Aftercomplete of reaction, the mixture was poured into ice-water, theformed solid was collected, washed with water and recrystallizedfrom ethanol-water to furnish the final compounds 4a-f and 8a-l[58-61].
Stage #1: 5-chloroindole 2,3-dione With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide 2.1.General procedure for the synthesis of N1-alkylated-isatin/N1-alkylated-5-chloroisatinderivatives (3 or 4) General procedure: The isatin/5-chloroisatin1(1 equiv.) and solid K2CO3 (1.2 equiv.) were taken ina 100 ml round bottom flask containing DMF (30 ml) as the solvent and thereaction was stirred for half-an-hour.The appropriate alkyl/benzyl bromide 2(1.2 equiv.) was added to the reaction mixture and stirred continuously for10-12 h until the starting material was consumed (monitored by TLC). Thereaction mixture was diluted with water (50 mL) and extracted with EtOAc (2 ×50 mL). The organic layer was washed with brine (2 × 50 mL), dried over anhydrousNa2SO4 and filtered. The filtrate was evaporated and thecrude product was purified by using silica gel column chromatography (EtOAc:hexane = 3:7; Rf 0.7), as the red solid products (3 and 4) in 70-80% yields. The structures were established on the basisof their spectroscopic data and these were identical in all respects to thosereported earlier.[1,2]
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 3h; Reflux; 5.1.3. Preparation of N-alkyl/benzyl isatin derivatives 6a-o General procedure: To a stirred mixture of isatins 3a-c (3.4 mmol), potassium carbonate(0.94 g, 6.8 mmol) and catalytic amount of potassium iodidein dry DMF (10 mL), the appropriate alkyl halide 5a-d (3.7 mmol) or benzyl bromide 5e (0.63 g, 3.7 mmol) was added, and the mixture was heated under reflux for 3 h. Then, the reaction mixture was poured into ice-water, the obtained solid was collected, washed several times with water, and recrystallized from ethyl alcohol to afford the N-substituted isatin derivatives 6a-o [27].
Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil Cooling with ice; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.25h; Cooling with ice;
Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h;
With Cs2CO3 In N,N-dimethyl-formamide at 24.84℃; for 12h; 2.1. Synthesis and crystallization Isatins (A) (see Scheme 1), where X = H or Cl, wereconverted to the corresponding N-alkyl analogues (B) byreaction with the appropriate alkyl bromide in dimethylformamide solution in the presence of solid caesium carbonateacting as a weak base, giving yields in excess of 90% after areaction time of 12 h at 298 K. For the synthesis of the 3-hydroxyindolin-2-ones, (I) (see Scheme 1), a mixture of an N-alkylisatin,(B) (1.0 mmol), the appropriate aryl methylketone (1.0 mmol) and piperidine (0.2 mmol) in ethanol(10 ml) was stirred at 298 K for 6 h [24 h in the case of compound (Id)], after which time the starting materials were no longer detectable using thin-layer chromatography (TLC).The resulting solid products were collected by filtration, washed with cold ethanol (2 ml) and dried in air to give the products of type (I).
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere; 2.0 General procedure for the synthesis of N-protected isatins1 1 (GP-1) General procedure: Commercially available isatins S1 were treated with different alkyl halides to prepare Nalkylatedwith in the presence of K2CO3 in DMF at room temperature for 8 h. To a stirredsolution of isatin S1 (1.0 g, 6.8 mmol, 1.0 equiv) and K2CO3 (2.3 g, 17.0 mmol, 3 equiv) in DMFwas added 1.5 equiv. of alkyl halide (MeI or BnBr or allyl bromide) and stirred for 8 h at roomtemperature. The reaction mixture was quenched with water and extracted with ethyl acetate (3 x20 mL). The combined organic fractions were washed with brine, dried over anhydrous Na2SO4,filtered and concentrated in vacuo. The crude residue was then purified by columnchromatography on silica gel with ethyl acetate-hexane (10/90 to 20/80) to provide compounds 1.
Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.333333h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.333333h;
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;
Stage #1: 5-chloroindole 2,3-dione With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃;
With potassium carbonate In N,N-dimethyl-formamide for 12h; Reflux;
With potassium carbonate In acetonitrile for 4h; Reflux;
Stage #1: 5-chloroindole 2,3-dione With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: benzyl bromide With potassium iodide In N,N-dimethyl-formamide Heating;
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 0.75h;

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[40]Cao, Weidi; Dai, Li; Feng, Xiaoming; Hu, Xinyue; Liu, Wen; Zeng, Zi; Zhou, Yuqiao [Angewandte Chemie - International Edition, 2021, vol. 60, # 51, p. 26599 - 26603][Angew. Chem., 2021, vol. 133, # 51, p. 26803 - 26807]
[41]Alkahtani, Saad; Anwar, Jamshed; Arshad, Nasima; Channar, Pervaiz Ali; Farooqi, Shahid Iqbal; Javaid, Memona; Javed, Aneela; Mir, Muhammad Ismail; Perveen, Fouzia; Saeed, Aamer [Molecules, 2022, vol. 27, # 2]
[42]Chen, Fen-Er; Li, Hong-Yan; Xiao, You-Cai; Xiong, Tong; Zhou, Li-Yan; Zhou, Yuan [Organic Letters, 2022, vol. 24, # 2, p. 791 - 796]
[43]Akdemir, Atilla; Berrino, Emanuela; Supuran, Claudiu T.; Bozdağ, Murat; Eraslan-Elma, Pınar; Karalı, Nilgün [Archiv der Pharmazie, 2022]
[44]Aboul-Fadl, Tarek; El-Sayed, Wael M.; Hassan, Mostafa A.; Qayed, Wesam S.; Rogério A. Silva, José [Bioorganic Chemistry, 2022, vol. 126]
  • 2
  • [ 17630-76-1 ]
  • [ 100-44-7 ]
  • [ 26960-68-9 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 48h; General Procedure for Synthesis of 1-Substituted-5-substituted-indoline-2,3-diones, 2b-f General procedure: Conventional Method (A)Benzyl chloride (4.1 mmol) was added dropwise to a mixtureof isatin derivatives 1 (3.4 mmol) and potassium carbonate(5.1 mmol) in DMF (10 mL) at 0°C and the reaction was stirredat room temperature for 48 h. The precipitate was poured intoan ice-water mixture. The resulting solid was filtered, washedwith water, dried, and re-crystallized from ethanol.
95% With potassium carbonate In N,N-dimethyl-formamide at 45 - 50℃; 2.2.1. General procedure for N -alkylation of 5-chloroisatin ( 2 and 3 ) General procedure: Following a reported procedure [54] , potassium carbonate (0.76 g, 5.52 mmoles, 2 equiv.) was added to a solution of 5- chloroisatin (0.50 g, 2.76 mmoles) in DMF (30 mL) taken in round bottom flask. After stirring the mixture for 30 min, corresponding alkyl halide (1.5 equiv.) was added and the resulting reaction mix- ture stirred for 3 h at 45-50 °C. Upon reaction completion (mon- itored by TLC), brine solution (20 mL) was added to quench the reaction. Extraction of product was accomplished by EtOAc thrice (20 mL ×3). The combined organic layer was dehydrated over an- hydrous magnesium sulfate and concentrated on rotary evaporator to obtain N -alkylated 5-chloroisatin. Recrystallization was executed from absolute ethanol and resulting shinny crystals were subjected to further characterizations (M.P., UV, FTIR, NMR, etc .).
71% With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 140℃; for 0.333333h; Microwave irradiation; To a 10 mL microwave vial charged with ethanol (3mL) and a magnetic stir bar was added 5-chloroisatin (0.3785 g, 2.08 mmol), DBU (329 μL, 1.1eq) and benzyl chloride (257 μL, 1.1 eq). The reaction vessel was sealed and heated undermicrowave irradiation in standard mode for 20 min at 140 oC with a pre-stirring 30 sec. Aftercooling to rt, the reaction vessel was placed in the freezer overnight but did not afford a solid.The resulting orange-red liquid was then evaporated under reduced pressure to afford an orangeoil which was purified by silica gel chromatography (hexanes/EtOAc, 70:30) to afford a pure(GC-MS/TLC) orange red solid (0.3875 g, 71%): mp 130-133 C (lit.14mp 134 oC); Rf = 0.65(hexanes:EtOAc,1:1). 1H NMR (300 MHz DMSO-d6) δ 7.63 (dd, J = 8.4 Hz, 2.2 Hz, 1H), 7.44ppm (d, J = 2.2 Hz, 1H), 7.37-7.28 (m, 5-H), 6.98 (d, J = 8.3 Hz, 1H), 4.91 (s, 2H); 13C NMR (75MHz DMSO-d6) δ 181.9, 158.1, 148.8, 136.7, 135.1, 129.7, 128.6, 127.5, 127.2, 123.9, 119.1,112.6, 42.9; MS (m/z) 271 (M+), 180 (100%).
65% Stage #1: 5-chloroindole 2,3-dione With aluminum oxide; potassium fluoride In acetonitrile for 0.166667h; Stage #2: benzyl chloride In acetonitrile for 47h; Reflux;
With potassium carbonate In N,N-dimethyl-formamide

  • 3
  • [ 26960-68-9 ]
  • [ 7396-44-3 ]
  • C24H18ClNO3 [ No CAS ]
  • 4
  • [ 26960-68-9 ]
  • [ 7396-44-3 ]
  • (±)-(trans)-benzyl 1-benzyl-5-chloro-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate [ No CAS ]
  • 5
  • [ 26960-68-9 ]
  • [ 604-44-4 ]
  • 1-benzyl-5-chloro-3-(1-chloro-4-hydroxynaphthalen-3-yl)-3-hydroxyindolin-2-one [ No CAS ]
  • 1-benzyl-5-chloro-3-(1-chloro-4-hydroxynaphthalen-3-yl)-3-hydroxyindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinu clidin-2-yl)methyl)thiourea; In tetrahydrofuran; at 25℃; for 6h;Molecular sieve; General procedure: To a solution of isatin derivatives (0.1 mmol), 1-naphthol (0.1 mmol), 4A MS (50 mg) in 0.3 mL of THF, the catalyst epiCDT (I,10 mol%) was added at 25 C. The reaction mixture was stirred for 6-60 hours and the progress of the reaction was monitored at regular intervals by thin layer chromatography (tlc). After the completion of reaction, the crude reaction mixture was purified by column chromatography on silica gel (mesh60-120) using hexane-ethyl acetate (1:1) as eluent. The enantiomeric excess of the purified Friedel-Crafts adducts 3 were determined using Diacel Chiralpak columns. The racemic standards were prepared using triethylamine (10 mol%) as a catalyst.
  • 6
  • [ 766-96-1 ]
  • [ 26960-68-9 ]
  • [ 1621167-81-4 ]
YieldReaction ConditionsOperation 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; 1-Benzyl-3-hydroxy-3-(phenylethynyl)-1,3-dihydro-2H-indol-2-one (3aa); Typical Procedure 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.
  • 7
  • [ 10075-50-0 ]
  • [ 26960-68-9 ]
  • [ 1621376-26-8 ]
YieldReaction ConditionsOperation in experiment
90% With copper(II) tungstate In water at 20℃; for 2h; Green chemistry; General procedure for the preparation of 3-hydroxy-3-(indol-3-yl)indolin-2-ones (5a-5t) and bis(indolyl)indolin-2-ones (6a-6p) General procedure: To a mixture of isatin (1 equiv.) and indole (1 or 2 equiv.) in water (3 mL), CuWO4 (10 mol%) was added and the mixture was stirred at room temperature for 2 h or heated at 60 °C for 2 h. After completion of the reaction (monitoring by TLC), the mixture was cooled (in the case of bis-indolyl-2-oxindoles) and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the desired product which was purified by silica gel column chromatography. Elution of the column with PE:EtOAc gave the desired products (5 or 6).
80% With 2,2'-iminobis[ethanol] In water at 20℃; Green chemistry; Typical experimental procedure for Friedal-Crafts reaction of isatins General procedure: To the reaction mixture containing isatin (0.5mmol) in water (2mL), indole (0.5mmol), diethanolamine (20mol %) was slowly added at room temperature. After thecompletion of reaction as monitored by TLC, the reaction mixture was washed with brine solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the product was purified by flash chromatography on the silica gel column using a gradient of petroleum ether/ethyl acetate, as eluent to afford pure products 1-41.
  • 8
  • [ 26960-68-9 ]
  • [ 105-56-6 ]
  • [ 762-42-5 ]
  • [ 3619-22-5 ]
  • 3'-ethyl 5',6'-dimethyl 2'-amino-1-benzyl-5-chloro-1'-(4-methylbenzamido)-2-oxo-1'H-spiro[indoline-3,4'-pyridine]-3',5',6'-tricarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: dimethyl acetylenedicarboxylate; p-toluic hydrazide In ethanol at 20℃; for 0.25h; Stage #2: 1-benzyl-5-chloroisatin; ethyl 2-cyanoacetate With triethylamine In ethanol at 20℃; for 24h; General procedure for the synthesis of 1,4-dihydropyridines 1a-1m via four-component reactions General procedure: In a round bottom flask, a solution of benzohydrazide or 2-picolinohydrazide (1.0mmol) and dimethyl acetylenedicarboxylate (1.0 mmol) in ethanol (15.0 mL) was stirred at room temperature for about fifteen minutes. Then, isatin (1.0 mmol), malononitrile or ethyl cyanoacetate(1.0 mmol) and triethylamine (0.2 mmol) was added. The mixture was stirred at room temperature for 24 hours. The resulting precipitates were collected by filtration and washed with cold alcohol to give the pure product for analysis
  • 9
  • [ 1570-45-2 ]
  • [ 26960-68-9 ]
  • [ 922-67-8 ]
  • C27H23ClN2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In 1,2-dimethoxyethane at 20℃; for 5h; 4 Experimental section 4.1 General procedure for the preparation of spirooxindoles 1a-1d from three-component reactions of substituted pyridine, electron-deficient alkynes, and isatins General procedure: 4 Experimental section 4.1 General procedure for the preparation of spirooxindoles 1a-1d from three-component reactions of substituted pyridine, electron-deficient alkynes, and isatins (0010) A mixture of substituted pyridine (1.0mmol), electron-deficient alkyne (1.2mmol), and isatin (1.0mmol) in 15.0mL of dimethoxyethane was stirred at room temperature for 5h. The solvent was removed by evaporation and the residue was crystallized with a mixture of chloroform and ethanol to give the product for spectroscopic analysis.
  • 10
  • [ 26960-68-9 ]
  • [ 16883-69-5 ]
  • [ 126-81-8 ]
  • 2-benzoyl-1'-benzyl-5'-chloro-6,6-dimethyl-6,7-dihydro-2H-spiro[benzofuran-3,3'-indoline]-2',4(5H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine In ethanol at 50℃; for 11h; 8 General procedure for the synthesis of compounds 4a-k General procedure: N-Phenacyl pyridinium bromide derivatives were obtainedby the reaction of phenacyl bromide derivatives andpyridine in acetonitrile medium. Triethylamine (1 mmol)was added to a mixture of isatin (1 mmol) and 1,3-dicarbonyl compounds (1 mmol) and N-phenacyl pyridiniumbromide in ethanol (5 ml) preheated at 50 C. Thereaction mixture was then stirred at 50 C for appropriatetime. After completion of the reaction, monitored by TLC onSiO2 using EtOAc/hexane (1:1) as the eluent, the solventwas removed under reduced pressure and the product wasobtained by recrystallization from diethyl ether.
  • 11
  • [ 26960-68-9 ]
  • [ 1149-24-2 ]
  • C27H25ClN2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With iron tungstate; In acetic acid; at 80℃; for 3.0h;Green chemistry; General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.
  • 12
  • [ 4971-56-6 ]
  • [ 26960-68-9 ]
  • [ 95-54-5 ]
  • 1'-benzyl-5'-chloro-4,9-dihydrospiro[benzo[b]furo[3,4-e][1,4]diazepine-10,3'-indoline]-1,2'(3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With aminosulfonic acid In water at 100℃; for 3h; General procedure for the synthesis of 4,9-dihydrospiro[benzo[b]furo[3,4-e][1,4]diazepine-10,3′-indoline]-1,2′(3H)-dione derivatives (4a-4u) General procedure: In 25 ml a round bottom flask with minimum amount of water as solvent at 80 °C, to this add o-phenylenediamine (1 mmol), tetronic acid (1 mmol), isatin (1 mmol) and sulphamic acid (4 mol %) it was stirred, refluxed at 100 °C for 3 h. The progress of reaction was monitored by TLC. After completion of the reaction, ice-cold water was added and stirred for 5 min. The precipitated solid collected by filtration, washed with water and recrystallised using ethanol.
  • 13
  • [ 26960-68-9 ]
  • [ 373-88-6 ]
  • [ 106-95-6 ]
  • C20H18ClF3N2O [ No CAS ]
  • 14
  • [ 26960-68-9 ]
  • [ 373-88-6 ]
  • [ 17435-72-2 ]
  • C23H22ClF3N2O3 [ No CAS ]
  • 15
  • [ 26960-68-9 ]
  • (E)-hex-2-en-4-ynedioic acid dimethyl ester [ No CAS ]
  • [ 51-35-4 ]
  • methyl (E)-1-benzyl-5-chloro-6'-hydroxy-1'-(3-methoxy-3-oxoprop-1-en-1-yl)-2-oxo-5',6',7',7a'-tetrahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol at 20℃; for 24h;
  • 16
  • [ 26960-68-9 ]
  • [ 1707-95-5 ]
  • 1'-benzyl-5'-chloro-10a,16c-dihydro-5H,12H-spiro[diindeno[2,1-b:2',1'-d]anthracene-11,3'-indoline]-2',5,10,12,17-pentaone [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine In toluene at 90℃; for 16h;
Same Skeleton Products
Historical Records