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Chemical Structure| 13380-67-1 Chemical Structure| 13380-67-1

Structure of 13380-67-1

Chemical Structure| 13380-67-1

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CAS No.: 13380-67-1

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Product Details of [ 13380-67-1 ]

CAS No. :13380-67-1
Formula : C10H6BrNO2
M.W : 252.06
SMILES Code : O=C(C=C1)N(C2=CC=C(Br)C=C2)C1=O
MDL No. :MFCD00030664
InChI Key :FECSFBYOMHWJQG-UHFFFAOYSA-N
Pubchem ID :123301

Safety of [ 13380-67-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 13380-67-1 ]

* 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.

  • Downstream synthetic route of [ 13380-67-1 ]

[ 13380-67-1 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 123972-87-2 ]
  • [ 13380-67-1 ]
  • [ 134939-31-4 ]
  • 2
  • [ 13380-67-1 ]
  • 2,5-diphenyl-3-trimethylsilylmethyl-1,3,4-thiadiazolium trifluoromethanesulfonate [ No CAS ]
  • 2,7a-diphenyl-5,6,7,7a-tetrahydropyrrolo[2,1-b][1,3,4]thiadiazole-endo-6,7-N-(p-bromophenyl)dicarboxyimide [ No CAS ]
  • 3
  • [ 59256-47-2 ]
  • [ 13380-67-1 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; acetic anhydride; for 2h;Reflux; General procedure: The synthesis of maleimides 1-47 was performed by mixing an equimolar amount of the appropriate maleic anhydrides 68-72 in 5 mL of CHCl3 and anilines 73, 78-90, amines 91-94 or phenylalkylamines 74-77 (5 mmol) dissolved in 1 mL of CHCl3 and stirred during 1 h. The solid (maleamic acid) which precipitated out of the reaction mixture was filtered off. The whole amount of maleamic acid was dissolved in 5 mL of acetic anhydride and 100 mg of sodium acetate was added. The mixture was heated for 2 h under reflux. The reaction was cooled and quenched with water; then, the aqueous solution was extracted with Et2O, dried with Na2SO4, filtered, and the solvent was evaporated. The product was purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (9:1) as eluent. Compounds 1-10, 16-26, 31-34, 36, 38-42 and 43-47 were previously reported.[3], [8], [21], [22], [23], [24], [25], [26], [27] and [28]
With sulfuric acid; acetic acid; at 60℃; for 0.75h; General procedure: Maleic anhydride (1.1 eq) was added at once with vigorous stirring in the solution of aniline (1.0 eq)in acetic acid (15 mL). It was stirred for another 10 minute while the reaction mixture turned into a suspension.To this reaction mixture concentrated sulphuric acid (2.0eq) was added at once while stirring. The temperature increased by 10oC and suspension turned into a clear solution. The temperature of reaction mixture was increased to 60oC and stirred furtherfor 45 minutes. It was allowed to come at room temperature and poured onto crushed ice. Thesolid separated was filtered and washed with water. The solid was transferred to the aqueous solution of sodium bicarbonate and stirred for 10 minutes to remove maleanilic acid if present. Then filtered and washed with water and recrystallized in ethanol. Yield: quantitative.
With sodium acetate; acetic anhydride; at 80℃; for 0.5h; General procedure: The maleamic acid was allowed to cyclodehydrated by using acetic anhydride and fused sodium acetate. The solution was stirred for 0.5 h at 80 C. The prepared produced is precipitated in ice, filtered and washed by water. The product was then crystallized by ethanol [6] (Fig. 1).
  • 4
  • [ 542-92-7 ]
  • [ 13380-67-1 ]
  • [ 72657-50-2 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 0.05h; General procedure: A mixture of the diene (1 mmol) and the dienophile (1 mmol)was subjected to hand grinding with a pestle and mortar for thetime shown in Tables 1 and 2 to afford the corresponding productsin quantitative yield. In the reactions of cyclopentadiene,1.2 equiv of the diene was used. In most cases, product formationwas observed by the change in color; with aryl maleimides,the yellow color of the initial reaction mixture changed to white, whereas with 1,3-diphenyl-2-benzofuran, the color of the mixture changed almost immediately from fluorescentgreen to white. 2-(4-Bromophenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3-dione (7b)White solid; yield: 317 mg (quant); mp 156 C. 1H NMR (500MHz, CDCl3): δ = 7.55 (dt, J = 2.5, 9.0 Hz, 2 H), 7.04 (dt, J = 2.5,9.5 Hz, 2 H), 6.25 (t, J = 1.5 Hz, 2 H), 3.53-3.47 (m, 2 H), 3.43 (q,J = 1.5 Hz, 2 H), 1.79 (d, J = 9.0 Hz, 1 H), 1.61 (d, J = 9.0 Hz, 1 H).13C NMR (125 MHz, CDCl3): δ = 176.3, 134.5, 132.1, 130.7, 128.1,122.2, 52.1, 45.7, 45.4.
  • 5
  • C-(4-methoxybenzyl)-N-phenylnitrone [ No CAS ]
  • [ 13380-67-1 ]
  • 5-(4-bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-cis-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione [ No CAS ]
  • 5-(4-bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-trans-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
31.3%; 40.1% In benzene; at 40℃; A mixture of C-(4-methoxybenzyl)-N-phenylnitrone (0.300 g, 1.32 mmol), <strong>[13380-67-1]N-(4-bromophenyl)maleimide</strong> (0.333 g, 1.32 mmol) and benzene (2.6 μL) was stirred overnight at 40 C. The resultant suspension was cooled to room temperature and diluted with methylene chloride until a homogeneous mixture was achieved. The mixture was chromatographed (silica gel, 20% ethyl acetate/hexanes). 5-(4-Bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-trans-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione eluted first and was isolated as a tan solid (0.254 g, 40.1%): mp 203-205 C. dec; 1H NMR (300 MHz, CDCl3) δ 7.50 (d, 4H), 7.32 (d, 2H), 7.20 (d, 2H), 7.04 (m, 3H), 6.60 (d, 2H), 5.75 (s, 1H), 5.15 (d, 1H), 4.06 (d, 1H), 3.86 (s, 3H); APCI MS m/z 481 [C24H19BrN2O4+H]+. 5-(4-Bromophenyl)-3-(4methoxyphenyl)-2-phenyl-cis-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione eluted second and was isolated as a tan solid (0.198 g, 31.3% yield): mp 206-208 C. dec; 1H NMR (300 MHz, CDCl3) δ 7.61 (d, 2H), 7.39 (d, 2H), 7.25 (d, 2H), 7.15 (d, 3H), 7.03 (d, 2H), 6.90 (d, 2H), 5.30 (d, 1H), 4.90 (d, 1H), 4.08 (t, 1H), 3.78 (s, 3H); APCI MS m/z 481 [C24H19BrN2O4+H]+. Illustrative compound 113 is formed by mixing 115 and 117 to form a 1:1 mixture
  • 6
  • [ 3585-93-1 ]
  • [ 13380-67-1 ]
  • 5-(4-bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-cis-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione [ No CAS ]
  • 5-(4-bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-trans-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
31.3%; 40.1% In benzene; at 40℃; A mixture of C-(4-methoxybenzyl)-N-phenylnitrone (0.300 g, 1.32 mmol), <strong>[13380-67-1]N-(4-bromophenyl)maleimide</strong> (0.333 g, 1.32 mmol) and benzene (2.6 mL) was stirred overnight at 40 C. The resultant suspension was cooled to room temperature and diluted with methylene chloride until a homogeneous mixture was achieved. The mixture was chromatographed (silica gel, 20% ethyl acetate/hexanes). 5-(4-Bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-trans-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione eluted first and was isolated as a tan solid (0.254 g, 40.1%): mp 203-205 C. dec; 1H NMR (300 MHz, CDCl3) δ 7.50 (d, 4H), 7.32 (d, 2H), 7.20 (d, 2H), 7.04 (m, 3H), 6.60 (d, 2H), 5.75 (s, 1H), 5.15 (d, 1H), 4.06 (d, 1H), 3.86 (s, 3H); APCI MS m/z 481 [C24H19BrN2O4+H]+. 5-(4-Bromophenyl)-3-(4methoxyphenyl)-2-phenyl-cis-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione eluted second and was isolated as a tan solid (0.198 g, 31.3% yield): mp 206-208 C. dec; 1H NMR (300 MHz, CDCl3) δ 7.61 (d, 2H), 7.39 (d, 2H), 7.25 (d, 2H), 7.15 (d, 3H), 7.03 (d, 2H), 6.90 (d, 2H), 5.30 (d, 1H), 4.90 (d, 1H), 4.08 (t, 1H), 3.78 (s, 3H); APCI MS m/z 481 [C24H19BrN2O4+H]+.
  • 7
  • [ 90-44-8 ]
  • [ 13380-67-1 ]
  • (R,R)-(-)-4-hydroxy-2-(4-bromophenyl)-3a,4,9,9a-tetrahydro-4,9-[1',2']-benzeno-1H-benz[f]isoindole-1,3(2H)-dione [ No CAS ]
  • [ 1041480-19-6 ]
YieldReaction ConditionsOperation in experiment
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In toluene; at 20℃; for 14h; General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
With (1R,2R)-N,N-dimethyl-N'-phthaloyl-1,2-diaminocyclohexane; In 1,2-dichloro-ethane; at -10℃; for 12h; General procedure: A mixture of maleimide 3 (0.24 mmol), anthrone 2 (0.2 mmol), and the catalyst (20 mol %) in 1,2-dichloroethane (0.6 mL) at -10 C was stirred for 12 h (monitored by TLC). After evaporation under reduced pressure, the residue was purified through column chromatography on silica gel (petroleum ether/ethyl acetate=3/1) to yield pure products.
  • 8
  • [ 1158818-80-4 ]
  • [ 13380-67-1 ]
  • C24H21BrN2O6S [ No CAS ]
  • 9
  • [ 108-31-6 ]
  • [ 106-40-1 ]
  • [ 13380-67-1 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In glacial acetic acid; at 60℃; General procedure: To a solution of the substituted anilines (0.01 mol) in acetic acid (10 mL), the maleic anhydride was added. The reaction mixture was stirred for 10 min. To this suspension, sulfuric acid (0.025 mol) was added while stirring. The temperature of the reaction mixture was then maintained at 60 C for 30-45 min. The cooled reaction mixture was poured onto crushed ice. The solid separated was collected, washed with aqueous sodium bicarbonate and then with water, and recrystallized from aqueous ethanol [64].
With manganese(II) acetate; acetic anhydride; triethylamine; In acetone; at 50 - 60℃; for 3h; The maleic anhydride and para-bromoaniline are dissolved in a certain amount of acetone solvent,The reaction solution was added dropwise to a reaction flask containing a maleic anhydride solution with stirring,Reaction exotherm and gradually produce light yellow precipitate, room temperature reaction 1 hour,Take a small amount of precipitation, washed,Dry, followed by adding manganese acetate,Triethylamine and acetic anhydride,After warming, the precipitate gradually dissolves,The reaction was carried out at 50 to 60 C for 2 hours,Solution from orange to red and black, the gradual emergence of new precipitation,Cooled to room temperature, the water precipitated by a large number of washed,Dried and recrystallized from acetone to give the product N-p-bromophenylmaleimide (3).
General procedure: 5 mmol of maleic anhydride was put into to 50mL three-necked round-bottom flask and dissolved in 10 mL of diethyl ether upon stirring. The flask was equipped with a dropping funnel and reflux condenser. Then, 5 mmol of the given aniline was dissolved in 3mL diethyl ether and added to the flask through the dropping funnel.The reaction mixture was stirred at room temperature for 1 h. Next,the reaction mixture was cooled to the room temperature, was filtered off and washed with diethyl ether to separate N-substituted maleic acid. Afterward, the dried product added to the flask and mixed with anhydrous sodium acetate (0.16 g, 2 mmol) and acetic anhydride (2 mL) then stirred for 1 h at 80 C. The reaction mixture was cooled to the room temperature and poured into an ice-water mixture. The product washed with 20 mL of ice-cold water 3 times.The dried crude was recrystallized from n-hexane or n-hexane/acetone to obtain the corresponding product.
With glacial acetic acid; for 6h;Reflux; General procedure: The maleimides needed for the photocatalytic annulation reactions were prepared using the reported procedure [1]. To a stirred solution of maleic anhydride (25 mmol) in acetic acid (15 mL) was added the amine (10 mmol). The reaction mixture was stirred at reflux for 6 h, and then the acetic acid was removed in vacuum. The residue was dissolved in CH2Cl2 (20 mL) and washed with aqueous NaHCO3 (2 × 30 mL), HCl (1 M, 2 × 30 mL), and saturated aqueous NaCl (30 mL). The organic layer was separated, dried over Na2SO4, and the solvent was removed in vacuum. Purification by flash chromatography afforded the desired maleimide substrates

  • 10
  • N-((tributylstannyl)methyl)-N-(6-(trimethylsilyl)hex-4-enyl)formamide [ No CAS ]
  • [ 13380-67-1 ]
  • 2-(4-bromophenyl)-9-vinyloctahydro-1H-pyrrolo[3,4-a]indolizine-1,3(2H)-dione [ No CAS ]
  • 11
  • [ 1143-38-0 ]
  • [ 13380-67-1 ]
  • [ 1242103-50-9 ]
YieldReaction ConditionsOperation in experiment
91% With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In toluene; at 20℃; for 14h; General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 12
  • [ 563-80-4 ]
  • [ 13380-67-1 ]
  • [ 1233703-87-1 ]
  • 13
  • [ 13380-67-1 ]
  • [ 67-64-1 ]
  • [ 1233703-75-7 ]
YieldReaction ConditionsOperation in experiment
86% With 2-([(1R,2R)-2-aminocyclohexyl]amino}[3,5-bis(trifluoromethyl)benzyl]amino}methylidene)-2,3-dihydro-1H-indene-1,3-dione; benzoic acid; In para-xylene; at 40℃; for 48h; General procedure: To a mixture of N-phenylmaleimide (4a, 34.6 mg, 0.200 mmol)and acetone (73.4 μL, 1.00 mmol) in p-xylene (0.4 mL) wasadded organocatalyst 3 (20.5 mg, 0.040 mmol) and benzoic acid(2.5 mg, 0.020 mmol) at r.t. After stirring in closed tube at 40 Cfor 48 h, the reaction mixture was directly purified by flashcolumn chromatography on silica gel with a 3:2 to 1:1 mixtureof hexane and EtOAc to afford 5a (37.3 mg, 81%) as a whitepowder.
86% With 2-([(1R,2R)-2-aminocyclohexyl]amino}[3,5-bis(trifluoromethyl)benzyl]amino}methylidene)-2,3-dihydro-1H-indene-1,3-dione; benzoic acid; In para-xylene; at 40℃; for 48h; General procedure: To a solution of N-phenylmaleimide 4a (34.6 mg, 0.200 mmol) and acetone (73.4 μL, 1.00 mmol) in p-xylene (0.4mL) were added organocatalyst 3 (20.5mg, 0.040 mmol) and benzoic acid (2.5 mg, 0.020 mmol) at room temperature. After stirring in a closed tube at 40C for 48 h, the reaction mixture was directly purified by flash column chromatography on silica gel with a 3:2-1:1 mixture of hexane and AcOEt to afford 5a (37.3 mg, 81%) as a white powder. 4.3.3 (S)-1-(4-Bromophenyl)-3-(2-oxopropyl)pyrrolidine-2,5-dione 5c 5c [α]D27 = +5.5 (c 1.0, CH2Cl2). 90% ee; Enantiomeric excess was determined by HPLC with ChiralCel OD-H column (hexane/2-propanol = 80:20), flow rate = 1.0 mL/min; λ = 220 nm; tmajor = 26.2 min, tminor = 45.3 min.
  • 14
  • [ 13380-67-1 ]
  • [ 78-84-2 ]
  • [ 1255928-87-0 ]
YieldReaction ConditionsOperation in experiment
87% With C30H45N3O4; benzoic acid; In toluene; at 20℃; General procedure: Aldehyde (2a, 0.40 mmol) was added to a mixture of a catalyst 1a or 1b (0.5 mol%), maleimide 3 (0.20 mmol), and 0.5 mol% PhCOOH in Toluene (1.0 mL). The reaction mixture was stirred at room temperature for the time required. After the maleimide had been consumed (monitored by TLC) the reaction mixture was subjected to thin layer chromatography on silica gel (ethyl acetate/hexane) to afford the pure Michael product 4. The enantiomeric excesses of the products 4 were determined by chiral HPLC analysis with Chiral columns.
64% With C29H49N3O2S; benzoic acid; In chloroform; at 20℃; General procedure: The aldehyde 5a or 5b (0.40 mmol) was added to a mixture of catalyst 1 (0.5 mg, 0.5 mol %), PhCOOH (1.2 mg, 5 mol %) and the corresponding maleimide 6 (0.20 mmol) in CHCl3 (0.5 mL). The reaction mixture was stirred at ambient temperature for the required time. After the maleimide was consumed (TLC analysis), the reaction mixture was subjected to thin layer chromatography on silica gel (ethyl acetate/petroleum ether) to afford the pure Michael product. The enantiomeric excess of the products was determined by chiral HPLC analysis using chiral columns.
  • 15
  • [ 1264932-06-0 ]
  • [ 13380-67-1 ]
  • [ 1264932-18-4 ]
  • 16
  • [ 503607-26-9 ]
  • [ 13380-67-1 ]
  • [ 1264932-19-5 ]
  • 18
  • [ 13380-67-1 ]
  • [ 4553-07-5 ]
  • [ 1312945-51-9 ]
  • C21H17BrN2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea; In 5,5-dimethyl-1,3-cyclohexadiene; at 20℃; for 7h; General procedure: A solution of α-phenyl cyanoacetates 1a (22.7 mg, 0.12 mmol), maleimide 1b (17.3 mg, 0.10 mmol), catalyst 4e (0.42 mg, 0.001 mmol) in xylene (0.5 mL) was stirred at room temperature for 7 h. After the solvent was evaporated under vacuum, the residue was purified by flash column chromatography over silica gel (petroleum ether/EtOAc = 3:1) to afford 3a as a white solid.
  • 19
  • [ 13380-67-1 ]
  • [ 42046-26-4 ]
  • 8-benzoyl-10-(4-bromophenyl)-8,8a,11a,11b-tetrahydro-5H-pyrrolo[3',4':3,4]pyrazolo[5,1-a]isoquinoline-9,11(6H,10H)-dione [ No CAS ]
  • 8-benzoyl-10-(4-bromophenyl)-8,8a,11a,11b-tetrahydro-5H-pyrrolo[3',4':3,4]pyrazolo[5,1-a]isoquinoline-9,11(6H,10H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,4-diaza-bicyclo[2.2.2]octane; In tetrahydrofuran; at 60℃; for 1h; General procedure: Toa solution of dry THF (0.6mL) were added N-Aryl maleimides 1 (0.10mmol), C,N-cyclic azomethine imines 2 (0.12 mmol) and catalyst V (0.02 mmol).The reaction mixture was stirred at 60 oC for 1-2h and then the solvent was extracted with H2O and DCM, dried with Na2SO4 and then concentrated under vacuum. The residue was purified by silica gel chromatography to yield the desired product 3.
  • 20
  • [ 13380-67-1 ]
  • [ 78-84-2 ]
  • [ 1352335-20-6 ]
YieldReaction ConditionsOperation in experiment
90% With C30H45N3O4; benzoic acid; In toluene; at 20℃; General procedure: Aldehyde (2a, 0.40 mmol) was added to a mixture of a catalyst 1a or 1b (0.5 mol%), maleimide 3 (0.20 mmol), and 0.5 mol% PhCOOH in Toluene (1.0 mL). The reaction mixture was stirred at room temperature for the time required. After the maleimide had been consumed (monitored by TLC) the reaction mixture was subjected to thin layer chromatography on silica gel (ethyl acetate/hexane) to afford the pure Michael product 4. The enantiomeric excesses of the products 4 were determined by chiral HPLC analysis with Chiral columns.
66% With C29H49N3O2S; benzoic acid; In chloroform; at 20℃; General procedure: The aldehyde 5a or 5b (0.40 mmol) was added to a mixture of catalyst 1 (0.5 mg, 0.5 mol %), PhCOOH (1.2 mg, 5 mol %) and the corresponding maleimide 6 (0.20 mmol) in CHCl3 (0.5 mL). The reaction mixture was stirred at ambient temperature for the required time. After the maleimide was consumed (TLC analysis), the reaction mixture was subjected to thin layer chromatography on silica gel (ethyl acetate/petroleum ether) to afford the pure Michael product. The enantiomeric excess of the products was determined by chiral HPLC analysis using chiral columns.
  • 21
  • [ 13380-67-1 ]
  • [ 123-54-6 ]
  • 1-(4-bromophenyl)-3-(2,4-dioxopentan-3-yl)pyrrolidine-2,5-dione [ No CAS ]
  • 22
  • [ 13380-67-1 ]
  • [ 78-84-2 ]
  • [ 1431769-35-5 ]
YieldReaction ConditionsOperation in experiment
With racemic primary amine thiourea organocatalyst; In dichloromethane; at 20℃; General procedure: In a typical experiment, a,a-disubstituted aldehyde(0.40 mmol), maleimides (0.20 mmol), and catalyst (0.03 mmol,15 mol%) in CH2Cl2 (0.5 mL) were stirred magnetically at room temperatureuntil the maleimide was consumed (monitored by TLC).The corresponding product was obtained after column chromatography(silica gel, eluent n-hexane/EtOAc). The enantiomeric excessof the products was determined by chiral HPLC analysis using chiralcolumns. All products were identified by spectroscopic data. Racemicsamples of the Michael adducts were prepared using racemiccatalyst. Compounds 6a'-6i' , 6m' and 6r' are known. The analyticaland spectroscopic data are in accordance with those reported.
With para-methylbenzylamine; In toluene; at 20℃; General procedure: Reference racemic samples of adducts 10 were obtained by performing the reaction using 4-methylbenzylamine (20mol%) as the organocatalyst in toluene as the solvent at room temperature.
  • 23
  • [ 13380-67-1 ]
  • [ 99-97-8 ]
  • (3aS*,9bR*)-2-(4-bromophenyl)-5,8-dimethyl-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione [ No CAS ]
  • 24
  • [ 13380-67-1 ]
  • [ 4553-07-5 ]
  • [ 1312945-51-9 ]
YieldReaction ConditionsOperation in experiment
93% With C31H53N3O2S; In toluene; at -30℃; for 2h; General procedure: The α-phenyl cyanoacetate 2 (0.10 mmol) was added to a mixture of catalyst 1a (10 mol %) and the corresponding maleimide 3 (0.12 mmol) in toluene (1.0 mL). The reaction mixture was stirred at -30 C for the required time. After the α-phenyl cyanoacetate was consumed as determined by TLC analysis, the reaction mixture was subjected to thin layer chromatography on silica gel (ethyl acetate/petroleum ether) to afford the pure Michael product.
  • 25
  • [ 13380-67-1 ]
  • [ 78-84-2 ]
  • [ 1255928-87-0 ]
  • [ 1352335-20-6 ]
YieldReaction ConditionsOperation in experiment
With C64H94N6O4S2; In dichloromethane; at 20℃; General procedure: In a typical experiment, a,a-disubstituted aldehyde(0.40 mmol), maleimides (0.20 mmol), and catalyst (0.03 mmol,15 mol%) in CH2Cl2 (0.5 mL) were stirred magnetically at room temperatureuntil the maleimide was consumed (monitored by TLC).The corresponding product was obtained after column chromatography(silica gel, eluent n-hexane/EtOAc). The enantiomeric excessof the products was determined by chiral HPLC analysis using chiralcolumns. All products were identified by spectroscopic data. Racemicsamples of the Michael adducts were prepared using racemiccatalyst. Compounds 6a'-6i' , 6m' and 6r' are known. The analyticaland spectroscopic data are in accordance with those reported.
With C64H94N6O4S2; In dichloromethane; at 20℃; General procedure: In a typical experiment, a,a-disubstituted aldehyde(0.40 mmol), maleimides (0.20 mmol), and catalyst (0.03 mmol,15 mol%) in CH2Cl2 (0.5 mL) were stirred magnetically at room temperatureuntil the maleimide was consumed (monitored by TLC).The corresponding product was obtained after column chromatography(silica gel, eluent n-hexane/EtOAc). The enantiomeric excessof the products was determined by chiral HPLC analysis using chiralcolumns. All products were identified by spectroscopic data. Racemicsamples of the Michael adducts were prepared using racemiccatalyst. Compounds 6a'-6i' , 6m' and 6r' are known. The analyticaland spectroscopic data are in accordance with those reported.
With Adipic acid; (S,S)-1,2-diaminocyclohexane; In water; N,N-dimethyl-formamide; at 25℃; for 24h; General procedure: To a solution of 6a, ent-6a or 6b (0.04mmol), the maleimide (0.2mmol) and hexanedioic acid (0.04mmol) in DMF/H2O (2:1, v/v) (0.5mL) was added the aldehyde (0.4mmol) and the mixture was stirred at room temperature until reaction completion (TLC). The reaction was then quenched with HCl 2M (10mL) and the mixture was extracted with AcOEt (3×10mL). The organic phase was washed with a saturated solution of NaHCO3 (10mL) and H2O (10mL), dried over MgSO4, and the filtrate was concentrated to give a crude product, which was purified by silica gel chromatography (n-hexane/AcOEt).
With tert-butyl ((1S,2S)-2-aminocyclohexyl)carbamate; In chloroform; at 25℃; for 30h; General procedure: To a solution of 7 or ent-7 (0.04mmol) and 9 (0.2mmol) in DMF/H2O (2:1, v/v) (0.5mL) was added aldehyde 8 (0.4mmol) and the reaction was stirred at rt until completion (TLC). A solution of 2M HCl (10mL) was then added and the mixture was extracted with EtOAc (3×10mL). The organic phase was washed with water (2×10mL), dried (MgSO4), filtered, and evaporated (15torr). The resulting crude was purified by flash chromatography (hexane/AcOEt) to afford adducts 10, which gave consistent spectroscopic data with those reported in the literature.10j
With tert-butyl ((1S,2S)-2-aminocyclohexyl)carbamate; In water; N,N-dimethyl-formamide; at 25℃; for 30h; General procedure: To a solution of 7 or ent-7 (0.04mmol) and 9 (0.2mmol) in DMF/H2O (2:1, v/v) (0.5mL) was added aldehyde 8 (0.4mmol) and the reaction was stirred at rt until completion (TLC). A solution of 2M HCl (10mL) was then added and the mixture was extracted with EtOAc (3×10mL). The organic phase was washed with water (2×10mL), dried (MgSO4), filtered, and evaporated (15torr). The resulting crude was purified by flash chromatography (hexane/AcOEt) to afford adducts 10, which gave consistent spectroscopic data with those reported in the literature.10j
With Adipic acid; (S,S)-2-(pyrimidin-2-ylamino)cyclohexaneamine; In water; N,N-dimethyl-formamide; at 0℃; for 72h;Catalytic behavior; General procedure: To a solution of 8 or ent-8(0.03 mmol), maleimide (0.3 mmol), and hexanedioic acid (0.03 mmol, 10% mol) in DMF-H2O (2:1, 0.6 mL) was added the aldehyde (0.6 mmol) and the mixture was stirred at 0 C until completion of the reaction (TLC) (times are given in Scheme 2). Then, aq 2 M HCl (10 mL) was added and the mixture was extracted with EtOAc (3 ×10 mL). The combined organic phases were washed with H2O (2 × 10 mL), dried (MgSO4), filtered, and evaporated (20 mbar). The resulting crude was purified by flash chromatography (n-hexane-EtOAc) to afford adduct 9.
With Methyltriphenylphosphonium bromide; Veratric acid; tert-butyl ((1S,2S)-2-aminocyclohexyl)carbamate; In glycerol; at 25℃; for 8h;Green chemistry; General procedure: To a mixture of catalyst 1 (0.02 mmol), additive (0.02 mmol),and maleimide (0.2 mmol) in the corresponding deep eutectic solvent(0.5 mL) was added the aldehyde (0.4 mmol) and the reaction was vigorously stirred during the necessary reaction time (TLC,Table 2) at rt. Next 2 M HCl (10 mL) was added and the mixture was extracted with AcOEt (3 10 mL). The combined organics were washed with aq NaHCO3 (2 10 mL), dried (MgSO4) and evaporated (15 torr), and the resulting crude was purified by flash chromatography (hexane/EtOAc gradients) affording adduct 4.
With sodium hydroxide; (S)?3?(2?amino?N?benzyl?3?phenylpropanamido)propanoic acid; In neat (no solvent); at 20℃; for 24h; General procedure: 15.6 mg (0.05 mmol) of α,β-dipeptide2, 2 mg (0.05 mmol) of NaOH, 0.5 mmol (1 equiv.) of the corresponding maleimide and2.75 mmol (5.5 equiv.) of the aldehyde were placed in a flask equipped with a magneticstirrer. The reaction mixture was stirred for up to 24 h at ambient temperature, until thin layerchromatography (TLC) showed that the reaction was complete. The product was purified byflash column chromatography with a mixture of hexanes/EtOAc (7:3) as eluent. The absolute configuration of the products was assigned by comparison with the available literature [45,55-57,76,77].The enantiomeric ratio was determined by chiral HPLC. NMR spectra and chromatograms can befound in Supplementary Materials.
With C66H96N2O23; sodium hydroxide; In dichloromethane; at 20℃; for 24h;Catalytic behavior; General procedure: Into a vial (8 cm3) equipped with stirring bar, 37 mg (0.05 mmol) of organocatalyst(H2N-Phe-N-Bn-β-Ala-TME-d-1G-A, 14), 0.5 mmol (1equiv.) of the N-phenylmaleimide (23a), 2 mg (0.05 mmol)of NaOH, 2.75 mmol (5.5 equiv.) of isobutyraldehyde (22),and 0.5 cm3 of solvent (H2O or CH2Cl2)were added. The reaction mixture was stirred for 24 h (up to 72 h) at room temperature. The crude product was purified by flash chromatographic column (hexanes/EtOAc, 7:3). The absolute configuration of the products was assigned in accordance with the literature [13, 66, 67] and the enantiomeric ratio(e.r.) was determined by chiral HPLC (see SupportingInformation).

  • 26
  • [ 872-53-7 ]
  • [ 13380-67-1 ]
  • (S)-1-(1-(4-bromophenyl)-2,5-dioxopyrrolidin-3-yl)cyclopentanecarbaldehyde [ No CAS ]
  • (R)-1-(1-(4-bromophenyl)-2,5-dioxopyrrolidin-3-yl)cyclopentanecarbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C64H94N6O4S2; In dichloromethane; at 20℃; General procedure: In a typical experiment, a,a-disubstituted aldehyde(0.40 mmol), maleimides (0.20 mmol), and catalyst (0.03 mmol,15 mol%) in CH2Cl2 (0.5 mL) were stirred magnetically at room temperatureuntil the maleimide was consumed (monitored by TLC).The corresponding product was obtained after column chromatography(silica gel, eluent n-hexane/EtOAc). The enantiomeric excessof the products was determined by chiral HPLC analysis using chiralcolumns. All products were identified by spectroscopic data. Racemicsamples of the Michael adducts were prepared using racemiccatalyst. Compounds 6a'-6i' , 6m' and 6r' are known. The analyticaland spectroscopic data are in accordance with those reported.
With C64H94N6O4S2; In dichloromethane; at 20℃; General procedure: In a typical experiment, a,a-disubstituted aldehyde(0.40 mmol), maleimides (0.20 mmol), and catalyst (0.03 mmol,15 mol%) in CH2Cl2 (0.5 mL) were stirred magnetically at room temperatureuntil the maleimide was consumed (monitored by TLC).The corresponding product was obtained after column chromatography(silica gel, eluent n-hexane/EtOAc). The enantiomeric excessof the products was determined by chiral HPLC analysis using chiralcolumns. All products were identified by spectroscopic data. Racemicsamples of the Michael adducts were prepared using racemiccatalyst. Compounds 6a'-6i' , 6m' and 6r' are known. The analyticaland spectroscopic data are in accordance with those reported.
  • 27
  • [ 872-53-7 ]
  • [ 13380-67-1 ]
  • 1-(1-(4-bromophenyl)-2,5-dioxopyrrolidin-3-yl) cyclopentanecarbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With racemic primary amine thiourea organocatalyst; In dichloromethane; at 20℃; General procedure: In a typical experiment, a,a-disubstituted aldehyde(0.40 mmol), maleimides (0.20 mmol), and catalyst (0.03 mmol,15 mol%) in CH2Cl2 (0.5 mL) were stirred magnetically at room temperatureuntil the maleimide was consumed (monitored by TLC).The corresponding product was obtained after column chromatography(silica gel, eluent n-hexane/EtOAc). The enantiomeric excessof the products was determined by chiral HPLC analysis using chiralcolumns. All products were identified by spectroscopic data. Racemicsamples of the Michael adducts were prepared using racemiccatalyst. Compounds 6a'-6i' , 6m' and 6r' are known. The analyticaland spectroscopic data are in accordance with those reported.
  • 28
  • [ 97-96-1 ]
  • [ 13380-67-1 ]
  • (S)-2-(1-(4-bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-ethylbutanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With C64H94N6O4S2; In dichloromethane; at 20℃; General procedure: In a typical experiment, a,a-disubstituted aldehyde(0.40 mmol), maleimides (0.20 mmol), and catalyst (0.03 mmol,15 mol%) in CH2Cl2 (0.5 mL) were stirred magnetically at room temperatureuntil the maleimide was consumed (monitored by TLC).The corresponding product was obtained after column chromatography(silica gel, eluent n-hexane/EtOAc). The enantiomeric excessof the products was determined by chiral HPLC analysis using chiralcolumns. All products were identified by spectroscopic data. Racemicsamples of the Michael adducts were prepared using racemiccatalyst. Compounds 6a'-6i' , 6m' and 6r' are known. The analyticaland spectroscopic data are in accordance with those reported.
  • 29
  • [ 97-96-1 ]
  • [ 13380-67-1 ]
  • (S)-2-(1-(4-bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-ethylbutanal [ No CAS ]
  • (R)-2-(1-(4-bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-ethylbutanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C64H94N6O4S2; In dichloromethane; at 20℃; General procedure: In a typical experiment, a,a-disubstituted aldehyde(0.40 mmol), maleimides (0.20 mmol), and catalyst (0.03 mmol,15 mol%) in CH2Cl2 (0.5 mL) were stirred magnetically at room temperatureuntil the maleimide was consumed (monitored by TLC).The corresponding product was obtained after column chromatography(silica gel, eluent n-hexane/EtOAc). The enantiomeric excessof the products was determined by chiral HPLC analysis using chiralcolumns. All products were identified by spectroscopic data. Racemicsamples of the Michael adducts were prepared using racemiccatalyst. Compounds 6a'-6i' , 6m' and 6r' are known. The analyticaland spectroscopic data are in accordance with those reported.
  • 30
  • [ 97-96-1 ]
  • [ 13380-67-1 ]
  • 2-(1-(4-bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-ethylbutanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
With racemic primary amine thiourea organocatalyst; In dichloromethane; at 20℃; General procedure: In a typical experiment, a,a-disubstituted aldehyde(0.40 mmol), maleimides (0.20 mmol), and catalyst (0.03 mmol,15 mol%) in CH2Cl2 (0.5 mL) were stirred magnetically at room temperatureuntil the maleimide was consumed (monitored by TLC).The corresponding product was obtained after column chromatography(silica gel, eluent n-hexane/EtOAc). The enantiomeric excessof the products was determined by chiral HPLC analysis using chiralcolumns. All products were identified by spectroscopic data. Racemicsamples of the Michael adducts were prepared using racemiccatalyst. Compounds 6a'-6i' , 6m' and 6r' are known. The analyticaland spectroscopic data are in accordance with those reported.
  • 31
  • [ 819045-73-3 ]
  • [ 13380-67-1 ]
  • methyl 2-(1-(4-bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-isocyano-2-phenylacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at 20℃; for 2h; General procedure: Racemic Michael adducts for chiral HPLC analysis were prepared from the corresponding isocyanoacetates 1 (0.24mmol) and maleimides 2 (0.20mmol) in the presence of DABCO (20mol%) in 2.0mL of DCM at room temperature for 2h.
  • 32
  • [ 819045-73-3 ]
  • [ 13380-67-1 ]
  • [ 1364041-25-7 ]
  • [ 1493805-97-2 ]
YieldReaction ConditionsOperation in experiment
With C31H29F3N4O3; In dichloromethane; at 20℃; for 72h;Molecular sieve; General procedure: A solution of isocyanoacetates 1 (0.30mmol), N-substituted maleimides 2 (0.15mmol), cat. 3f (8.9mg, 0.015mmol), and 4 MS (30mg) in DCM (1.0mL) was stirred at 20C for 3d. And then the reaction mixture was concentrated and the residue was directly subjected to flash column chromatography on silica gel (petroleum ether/ethyl acetate=4:1) to furnish the corresponding products 5. 4.2.3 (R)-Methyl 2-((R)-1-(4-bromophenyl)-2,5-dioxopyrrolidin-3-yl)-2-isocyano-2-phenylacetate (5c) 10c Pale-yellow solid (53.2 mg, 82%); mp 187.0-190.3 C. 20:1 dr. -41.4 (c 1.0, CH2Cl2); 87% ee (Chiralcel OD-H; hexane/2-propanol, 60:40; 1.0 mL/min; 230 nm; tmajor=10.76 min, tminor=19.57 min). 1H NMR (400 MHz, CDCl3): δ=7.64-7.59 (m, 4H, ArH), 7.55-7.47 (m, 3H, ArH), 7.24-7.20 (m, 2H, ArH), 4.43 (dd, J=9.6, 6.0 Hz, 1H, CH), 3.88 (s, 3H, OCH3), 2.80 (dd, J=18.8, 9.6 Hz, 1H, CH), 2.52 (dd, J=18.8, 6.0 Hz, 1H, CH) ppm. 13C NMR (100 MHz, CDCl3): δ=173.2, 172.7, 166.5, 164.4, 132.5, 131.8, 130.1, 130.0, 129.6, 128.0, 125.4, 123.0, 71.0, 54.6, 48.3, 30.6 ppm. IR (film): ν=2361, 2342, 2131, 1751, 1716, 1489, 1384, 1245, 1177, 1035 cm-1.
 

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