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Chemical Structure| 4338-06-1 Chemical Structure| 4338-06-1

Structure of 4338-06-1

Chemical Structure| 4338-06-1

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Product Details of [ 4338-06-1 ]

CAS No. :4338-06-1
Formula : C10H6N2O4
M.W : 218.17
SMILES Code : O=C(N1C2=CC=C([N+]([O-])=O)C=C2)C=CC1=O
English Name :1-(4-Nitrophenyl)-1H-pyrrole-2,5-dione
MDL No. :MFCD00022576

Safety of [ 4338-06-1 ]

Application In Synthesis of [ 4338-06-1 ]

* 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 [ 4338-06-1 ]

[ 4338-06-1 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 4338-06-1 ]
  • [ 78-84-2 ]
  • [ 1242461-32-0 ]
YieldReaction ConditionsOperation in experiment
100% With (S)-3-amino-3-phenylpropanoic acid; caesium carbonate In dichloromethane at 20℃; for 24h; enantioselective reaction;
98% With C64H94N6O4S2 In dichloromethane at 20℃; enantioselective reaction; Representative procedure for the Michael addition 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.
93% With C30H45N3O4; benzoic acid In toluene at 20℃; enantioselective reaction; III. Typical procedure for the Michael reaction 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.
87% With C13H19N3S In chloroform; water at 20℃; for 0.83h; optical yield given as %ee; enantioselective reaction;
80% With NH2-Phg-(D-Pro)-Gly-Leu-OH In acetonitrile at 20℃; for 72h; enantioselective reaction;
75% With C29H49N3O2S; benzoic acid In chloroform at 20℃; optical yield given as %ee; enantioselective reaction; 4.3. Typical procedure for the Michael addition 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.
71% With C26H43N3OS In toluene at 20℃; enantioselective reaction;
With (R)-3-phenyl-3-aminopropionic acid; potassium hydroxide In dichloromethane at 20℃; for 24h; enantioselective reaction;

  • 2
  • [ 4338-06-1 ]
  • [ 88014-09-9 ]
  • [ 1323921-42-1 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: N-(4-nitrophenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester With tert.-butylhydroperoxide; Rh2(cap)4*2CH3CN; potassium carbonate In decane; acetonitrile Stage #2: With N-Bromosuccinimide In decane; acetonitrile for 1h; General experimental procedure: General procedure: Rh2(cap)42CH3CN(0.0015mmol),tetrahydroisoquinoline 1(0.36mmol),and K2CO3(0.15mmol)inCH3CN(2.0mL)were mixed and kept under stirring while t-BuOOH (5.5Mindecane,0.60 mmol)was added inone portion atroom temperature.Then N-phenylmaleimide 2(0.30mmol)inCH3CN(1.0mL)was added dropwise over 2husing asyringe pump.The reaction was stirred until substrate 2was completely consumed (ca.3h),and then N-bromosuccinimide (0.60mmol)was added and stirring continued for 1h.Saturated NaHSO 3(5mL)was added toquench the reaction.The crude mixture was extracted with CH2Cl2(10mL3),and the combined organic phases were dried over sodium sulfate andfiltered.The filtratewas concentrated and the residue purifiedbyflashcolumnchromatography onsilica gel using petroleum ether-dichloromethane-ethyl acetate asthe eluent,giving the desired product 3.The structures ofthe cycloadducts3a-lwere identifiedbycomparison with the1HNMR spectra inRef.4and confirmedbymass spectra.
87.1% Stage #1: N-(4-nitrophenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester With oxygen In dichloromethane at 20℃; for 2h; Irradiation; Stage #2: With N-Bromosuccinimide at 20℃; for 1h;
84% With N-Bromosuccinimide; C88H30BF2N3 In dichloromethane at 20℃; for 1h; Irradiation;
81% With dihydrogen peroxide; iodine In water; N,N-dimethyl-formamide at 80℃; for 6h;
81% With tert.-butylhydroperoxide; potassium iodide In water; N,N-dimethyl-formamide at 80℃; for 9h; Green chemistry;
80% With N-Bromosuccinimide; C80H68B3F6I2N13O4; oxygen In dichloromethane at 20℃; for 1.5h; Irradiation;
72% With N-Bromosuccinimide In acetonitrile at 20℃; for 1h; UV-irradiation;
68% Stage #1: N-(4-nitrophenyl)maleimide; (3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester With [Ru(bpy)3]Cl2; oxygen In acetonitrile at 20℃; for 12.5h; Irradiation; Stage #2: With N-Bromosuccinimide In acetonitrile at 20℃; for 1h;
53% With N-Bromosuccinimide; C65H61BF2I2N7O3(1+) In dichloromethane for 1.5h; Irradiation;
79 %Chromat. With cadmium sulphide In neat (no solvent) at 20℃; for 24h; Irradiation; Green chemistry;

  • 3
  • [ 4338-06-1 ]
  • [ 78-84-2 ]
  • [ 1319746-62-7 ]
YieldReaction ConditionsOperation in experiment
97% With 1-[(1R,2R)-2-amino-1,2-diphenylethyl]-3-[3,5-bis(trifluoromethyl)phenyl]thiourea In water at 20℃; for 12h; Green chemistry; stereoselective reaction; 3.2.2. Asymmetric Michael Reaction of Aldehyde and Maleimide Using a Chiral Thiourea Catalyst General procedure: At room temperature, an N-mono-thiourea catalyst (0.01 mol%) and N-phenylmaleimide (2.88 mmol) were placed in a reaction vessel and then dissolved with water (0.1 mL) in air. Then, aldehyde (2 equiv.) was added to the mixture, which was stirred for 10-13 h.After the reaction was terminated with distilled water, the mixture was extracted with ethylacetate (0.3 mL 3 times), dehydrated using MgSO4, filtered, concentrated under reducedpressure, and purified using column chromatography (SiO2, CH2Cl2: n-hexane = 1:3) toisolate the product.
91% With C30H45N3O4; benzoic acid In toluene at 20℃; enantioselective reaction; III. Typical procedure for the Michael reaction 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.
86% With 1-[(1R,2R)-2-aminocyclohexyl]-3-[4-(n-perfluorooctyl)phenyl]-thiourea In dichloromethane at 20℃; for 48h; optical yield given as %ee; enantioselective reaction; A typical procedure of Michael reaction using 3 and 7a is as follows General procedure: To a solution of 7a (277 mg, 1.60 mmol) and fluorous organocatalyst 3 (107 mg, 0.160 mmol) in 20 mL of CH2Cl2 was added isobutyl aldehyde (293 μL, 3.20 mmol) at room temperature. After stirring at room temperature for 22 h, the reaction mixture was evaporated under reduced pressure. Then, a 1:1 mixture of hexane and chloroform was added to the residue. The precipitated fluorous organocatalyst 3 was filtered, and washed with a 1:1 mixture of hexane and chloroform. The collected 3 was dried under reduced pressure, and was used in the next step without further purification. The filtrate was evaporated, and the residue was purified by flash column chromatography on silica gel with a 2:1 mixture of hexane and AcOEt to afford the pure 8a (343 mg, 87%) as a colorless powder.
70% With C29H49N3O2S; benzoic acid In chloroform at 20℃; optical yield given as %ee; enantioselective reaction; 4.3. Typical procedure for the Michael addition 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.
70% With C26H43N3OS In toluene at 20℃; enantioselective reaction;

  • 4
  • [ 4338-06-1 ]
  • [ 78-84-2 ]
  • [ 1242461-32-0 ]
  • [ 1319746-62-7 ]
YieldReaction ConditionsOperation in experiment
With (S)-1-(1-amino-3-phenylpropan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea In dichloromethane at 20℃; for 48h; optical yield given as %ee; enantioselective reaction; 4.3. Typical procedure for a Michael reaction using organocatalyst 8 (Table 2) A typical procedure for a Michael reaction using 8 and 11a is as follows: to a solution of thiourea organocatalyst 8 (16.8 mg, 40.0 μmol) in 1 mL of CH2Cl2 were added isobutyraldehyde (147 μL, 1.60 mmol) and 11a (139 mg, 0.80 mmol) at room temperature. After stirring at room temperature for 24 h, the reaction mixture was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel with a 2:1 mixture of hexane and AcOEt to afford the pure 12a (188 mg, 96%) as a colorless powder. All the Michael addition products in the paper are known compounds that exhibited spectroscopic data identical to those reported in the literature.
86 % ee With L-Asp(t-Bu); potassium hydroxide In dichloromethane at 20℃; for 24h; Overall yield = 74 %; enantioselective reaction;
88 % ee With C64H94N6O4S2 In dichloromethane at 20℃; Overall yield = 96 %; enantioselective reaction; Representative procedure for the Michael addition 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.
70 % ee With C13H18N2O2 In toluene at 20℃; for 48h; Overall yield = 78%; Overall yield = 45 mg; enantioselective reaction; 3.2. General Procedure for the Asymmetric Conjugate Addition Reaction General procedure: A solution of 15 (0.02 mmol, 4,7 mg) and the maleimide 17 (0.2 mmol) in toluene (0.5 mL) was added to the aldehyde 16 (0.4 mmol), and the mixture was stirred at rt for 48 h (TLC). The reaction was quenched with HCl 2 N (10 mL) and the mixture was extracted with AcOEt (3 10 mL).The organic phase was washed with saturated NaHCO3 (10 mL) and brine (10 mL), dried over MgSO4,filtered, and the solvent was then evaporated (15 Torr) to get the crude product, which was purified bysilica gel chromatography (n-hexane/AcOEt gradients). Adducts 18 were identified by the comparisonof their 1H-NMR data with those of the literature. Their enantiomeric excesses were determined bychiral HPLC using the conditions described in each case.
77 % ee With (R)-10-camphorsulfonic acid In dichloromethane at 20℃; Overall yield = 58 percent; enantioselective reaction; 2.4. General procedure for asymmetric Michael reactions General procedure: To a mixture of nitroalkene (1 equiv.) or maleimide (1 equiv.), (S,S)or (R,R) GO-PATU (25 mg) and additive (0.015 mmol) in CH2Cl2 (1.0mL) was added isobutyraldehyde 5a or cyclopentanecarboxaldehyde 5b (4 eq. or 5 eq.) at room temperature. The mixture was stirred until the comsuming of starting material had been detected by TLC (24 to 72 h). Then, the mixture was centrifuged and the DCM layer was separated. The solvent was evaporated and the residue was purified through a 10cm pad of silica gel placed in a Pasteur pipette by flushing hexane/ethylacetate mixture. Racemic samples of the Michael adducts were preparedusing a racemic primary amine thiourea organocatalyst. All addition products 7a-7g and 9a-9f are known and the analytical and spectroscopic data are in accordance with those reported (see Supplementarymaterial) [27,28].

  • 5
  • [ 4338-06-1 ]
  • [ 29753-26-2 ]
YieldReaction ConditionsOperation in experiment
50.5% With hydrogenchloride; tin(ll) chloride In water at 61℃; for 17h; Inert atmosphere; 1.1; 2.1; 3.1; 4.1; 5.1; 6.1 (1) In a nitrogen atmosphere, 56.4 g of N-(4-nitrophenyl)maleimide, 67.6 g of stannous chloride, and 525 mL of 10 mol / L hydrochloric acid are mixed uniformly.The reaction was performed at 61 ° C for 17 hours. After the completion of the reaction was detected by TLC thin-layer analysis, the obtained reaction solution was transferred to a beaker.Add sodium hydroxide to adjust the pH of the solution to 7, and add 3 times with ethyl acetate (the total volume of ethyl acetate is 3 times the volume of the reaction solution),The obtained organic phases were combined, dried over anhydrous magnesium sulfate, and then filtered with suction, and subjected to rotary evaporation at 45 ° C. N-(4-aminophenyl)maleimide was obtained (light yellow solid, 26.3 g, yield 50.5%);
90 %Chromat. With formic acid; triethylamine In tetrahydrofuran at 100℃; for 15h; Inert atmosphere; Sealed tube; chemoselective reaction;
70 %Chromat. With [Mo3S4Cl3(dnbpy)3](PF6); hydrogen In methanol at 70℃; for 18h; Autoclave;
With iron In ethanol

  • 6
  • [ 4338-06-1 ]
  • [ 121-69-7 ]
  • [ 2254658-02-9 ]
YieldReaction ConditionsOperation in experiment
93% With tert.-butylhydroperoxide; copper(II) acetate monohydrate In water at 20℃; for 1h; Representative procedure for the synthesisof ( ±)-5-methyl-2-phenyl-3a,4,5,9b-tetrahy-dro-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione (3a) General procedure: In a 10 mL reaction vial, N,N-dimethylaniline (18.2 mg,0.15 mmol), N-phenylmaleimide (17.3 mg, 0.1 mmol),TBHP (70% in H2O, 0.1 mmol, 14 µL) and copper(II)acetate monohydrate (1.99 mg, 0.01 mmol) were taken inwater (1.5 mL). The reaction vial was closed with a screwcap and stirred at room temperature. After 2 h, the reactionmixture was diluted with water and extracted with ethylacetate (2 × 5 mL). The combined organic extracts weredried over anhydrous sodium sulphate, filtered and theorganic solvents were evaporated under reduced pressureto afford the crude residue. The obtained crude residuewas purified by column chromatography using silica gel(100-200 mesh) with hexane and ethyl acetate as eluent(8:2) to afford the pure product.
71% With alizarin red S sensitized TiO2; air In acetonitrile at 30℃; for 20h; Irradiation;
52% With thiadiazolopyridine functionalized Zr(IV) based metal organic framework In acetonitrile at 20℃; for 12h; Irradiation;
90 %Chromat. With cadmium sulphide In neat (no solvent) at 20℃; for 36h; Irradiation;
93 % With tert.-butylhydroperoxide; copper(II) acetate monohydrate In water at 20℃; Green chemistry; Representative procedure for the synthesisof ( ±)-5-methyl-2-phenyl-3a,4,5,9b-tetrahy-dro-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione (3a) General procedure: In a 10 mL reaction vial, N,N-dimethylaniline (18.2 mg,0.15 mmol), N-phenylmaleimide (17.3 mg, 0.1 mmol),TBHP (70% in H2O, 0.1 mmol, 14 µL) and copper(II)acetate monohydrate (1.99 mg, 0.01 mmol) were taken inwater (1.5 mL). The reaction vial was closed with a screwcap and stirred at room temperature. After 2 h, the reactionmixture was diluted with water and extracted with ethylacetate (2 × 5 mL). The combined organic extracts weredried over anhydrous sodium sulphate, filtered and theorganic solvents were evaporated under reduced pressureto afford the crude residue. The obtained crude residuewas purified by column chromatography using silica gel(100-200 mesh) with hexane and ethyl acetate as eluent(8:2) to afford the pure product.

  • 7
  • [ 4338-06-1 ]
  • [ 2244696-61-3 ]
  • [ 2306460-80-8 ]
YieldReaction ConditionsOperation in experiment
91% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 120℃; for 80h; Inert atmosphere; 3 The method is specifically 1-Chloro-2-(3-methyl-but-2-enyl)-benzene (0.50 mmol) under the protection of an inert gas (nitrogen or argon), 2,3-dichloro-5,6-dicyanioquinone (0.4 mmol), N-(4-nitrophenyl)maleimide (0.20 mmol) was added to a Schlenk bottle, replacing nitrogen three times, adding 2 mL of chlorobenzene (distilled by calcium hydride), heating to 120 ° C for 80 h, TLC plate monitoring The reaction was completed, the solvent was evaporated under reduced pressure, and purified by column chromatography ( petroleum ether: ethyl acetate = 5:1) to give 6-methyl-2-(4-nitrophenyl)-4-(2-chloro Phenyl)-3a,4,7,7a-1H-tetrahydroisoindole-1,3(2H)-dione (white Color solid, yield 91%).
91% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 110℃; for 60h; Schlenk technique; Inert atmosphere; stereoselective reaction;
  • 8
  • [ 4338-06-1 ]
  • [ 1146120-91-3 ]
  • [ 2306460-82-0 ]
YieldReaction ConditionsOperation in experiment
93% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 110℃; for 60h; Inert atmosphere; 4 The specific steps of the method are as follows 1-Methyl-2-(3-methyl-but-2-enyl)-benzene (0.40 mmol) under the protection of an inert gas (nitrogen or argon),2,3-dichloro-5,6-dicyanioquinone (0.3 mmol),N-(4-nitrophenyl)maleimide (0.20 mmol) was added to a Schlenk bottle, the nitrogen was replaced three times, 2 mL of toluene (distilled by calcium hydride), heated to 110 ° C for 60 h, and monitored by TLC plate. The reaction was completed, the solvent was evaporated under reduced pressure, and then purified by column chromatography ( petroleum ether: ethyl acetate = 5:1) to give 6-methyl-2-(4-nitrophenyl)-4-(2-methylphenyl) -3a, 4,7,7a-1H-tetrahydroisoindole-1,3(2H)-dione (white solid, yield 93%)
93% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 110℃; for 60h; Schlenk technique; Inert atmosphere; stereoselective reaction;
  • 9
  • [ 4338-06-1 ]
  • [ 18272-91-8 ]
  • [ 2306460-84-2 ]
YieldReaction ConditionsOperation in experiment
91% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 110℃; for 60h; Inert atmosphere; 5; 8 The specific steps of the method are as follows 1-Methoxy-3-(3-methyl-but-2-enyl)-benzene (0.40 mmol) under the protection of an inert gas (nitrogen or argon),2,3-dichloro-5,6-dicyanioquinone (0.3 mmol),N-(4-nitrophenyl)maleimide (0.20 mmol) was added to a Schlenk bottle, replaced with nitrogen three times, 2 mL of dichloromethane (distilled with calcium hydride), heated to 110 ° C for 60 h, TLC plate After monitoring, the reaction was completed, and the solvent was evaporated under reduced pressure, and then purified by column chromatography ( petroleum ether: ethyl acetate = 5:1) to obtain 6-methyl-2-(4-nitrophenyl)-4-(3- Methoxyphenyl)-3a,4,7,7a-1H-tetrahydroisoindole-1,3(2H)-dione (white solid, yield 91%).
91% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 110℃; for 60h; Schlenk technique; Inert atmosphere; stereoselective reaction;
  • 10
  • [ 4338-06-1 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
87% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 100℃; for 40h; Inert atmosphere; 6 The specific steps of the method are as follows 1-Bromo-4-(3-methyl-but-2-enyl)-benzene (0.30 mmol) under the protection of an inert gas (nitrogen or argon),2,3-Dichloro-5,6-dicyano-p-benzoquinone (0.2 mmol), N-(4-nitrophenyl)maleimide (0.20 mmol) was added to a Schlenk bottle, and the nitrogen was replaced three times. 2mL of toluene (distilled water by hydrogenation of calcium hydride), heated to 100 ° C for 40 h, monitored by TLC plate, the reaction was completed, the solvent was evaporated under reduced pressure, and then purified by column chromatography ( petroleum ether: ethyl acetate = 5:1) to obtain 6- Methyl-2-(4-nitrophenyl)-4-(4-bromophenyl)-3a,4,7,7a-1H-tetrahydroisoindole-1,3(2H)-dione ( WhiteColor solid, yield 87%).
87% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 110℃; for 60h; Schlenk technique; Inert atmosphere; stereoselective reaction;
  • 11
  • [ 4489-84-3 ]
  • [ 4338-06-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
91% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 110℃; for 60h; Inert atmosphere; 1; 7 The method is specifically (3-Methyl-but-2-enyl)-benzene (0.40 mmol), 2,3-dichloro-5,6-dicyano-p-benzoquinone (0.3 mmol) under an inert gas (nitrogen or argon) N-(4-nitrophenyl)maleimide (0.20 mmol) was added to a Schlenk bottle, replacing nitrogen three times, adding 2 mL of chlorobenzene (distilled water by distillation of calcium hydride), heating to 110 ° C for 60 h, TLC The plate was monitored, the reaction was completed, the solvent was evaporated under reduced pressure, and purified by column chromatography ( petroleum ether: ethyl acetate = 5:1) to give 6-methyl-2-(4-nitrophenyl)-4-phenyl-3a,4,7,7a-1H-tetrahydroisoindole-1,3(2H)-dione (white solid,Yield 91%).
91% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 110℃; for 60h; Schlenk technique; Inert atmosphere; stereoselective reaction;
  • 12
  • [ 4338-06-1 ]
  • [ 2244696-59-9 ]
  • [ 2306460-79-5 ]
YieldReaction ConditionsOperation in experiment
87% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 100℃; for 40h; Inert atmosphere; 2 The method is specifically 1-fluoro-2-(3-methyl-but-2-enyl)-benzene (0.30 mmol) under the protection of an inert gas (nitrogen or argon),2,3-dichloro-5,6-dicyanioquinone (0.2 mmol),N-(4-nitrophenyl)maleimide (0.20 mmol) was added to a Schlenk bottle, replaced with nitrogen three times, 2 mL of chlorobenzene (distilled with calcium hydride), heated to 100 ° C for 40 h, TLC plate monitoring The reaction was completed, the solvent was evaporated under reduced pressure, and then purified by column chromatography ( petroleum ether: ethyl acetate = 5:1) to give 6-methyl-2-(4-nitrophenyl)-4-(2-fluoro Phenyl)-3a,4,7,7a-1H-tetrahydroisoindole-1,3(2H)-dione (white solid, yield 87%).
87% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 110℃; for 60h; Schlenk technique; Inert atmosphere; stereoselective reaction;
  • 13
  • [ 4338-06-1 ]
  • [ 121911-01-1 ]
  • [ 2362049-63-4 ]
YieldReaction ConditionsOperation in experiment
75% With chlorophyll a; oxygen In toluene at 20℃; for 30h; Irradiation; Green chemistry; 2.3. Typical Procedure for synthesis of Pyrrolo[2,1-a]isoquinoline derivatives General procedure: In a test tube, a mixture of dihydro isoquinoline ester 1a (0.263 g, 1.2 mmol), maleimide 2a (0.097 g, 1 mmol), and chlorophyll-a (4.0 mg) in toluene (4.0 mL) was irradiated under air atmosphere by 15 W white LED (λ > 410 nm, distance app. 9.0 cm) at rt. The reaction was monitored by TLC and after completion (30 h), the reaction mixture concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel with petroleum ether/ethyl acetate as eluent (9:1).
69% With N-hydroxyphthalimide; tetraethylammonium bromide In methanol at 25℃; for 12h; Electrochemical reaction; Green chemistry; regioselective reaction;
72 %Spectr. With alizarin red S; eosin Y disodium salt In acetone at 28℃; for 20h; Irradiation; 4.1.5. General procedure for the synthesis of Pyrrolo[2,1-a]isoquinoline derivatives General procedure: Typically, a mixture of tetrahydroisoquinoline ester 1a (1.2 mmol), maleimides 2a (1 mmol), and photocatalyst (EY- ARS,2 mol%: 4 mol %) in acetone (6 mL) was added to a flask under air atmosphere. Then, the mixture was stirred under the irradiation of a 15 W blue LED lamp (distance app. 5.0 cm) for 20 h at ambient temperature (28 C). After completion of the reaction (monitored by TLC), the reaction mixture concentrated in a rotary evaporator, and the residue was purified just by washing with acetone or by flash column chromatography on silica gel with petroleum ether/ethyl acetate as eluent. Other Pyrrolo[2,1-a]isoquinoline derivatives were prepared by a similar method except the solvent was changed to acetonitrile, respectively (in some cases prolonged time were applied) as well as the eluent ratio of flash column chromatography was changed regarding target products.
  • 14
  • [ 491-38-3 ]
  • [ 4338-06-1 ]
  • [ 2416167-73-0 ]
YieldReaction ConditionsOperation in experiment
61% With [Ru(p-cymene)Cl2]2; silver(I) acetate; silver(I) triflimide In 1,2-dichloro-ethane at 120℃; for 4h; 22 Example 22 At room temperature, chromone (0.2mmol),N- (4-nitrophenyl) maleimide (0.5 mmol), [Ru (p-cymene) Cl2] 2 (5 mol%),AgNTf2 (20 mol%), silver acetate (3equiv.), And DCE (2.0 mL).The temperature was raised to 120 ° C and stirred. TLC tracks the reaction. After 4 hours, the reaction was stopped.Water and ethyl acetate were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three times with ethyl acetate.Combine all organic layers, dry over anhydrous sodium sulfate, concentrate, and isolate by column chromatography (50% ethyl acetate in petroleum ether),44.2 mg of product was obtained with a yield of 61%,
61% With [Ru(p-cymene)Cl2]2; silver(I) acetate; silver(I) triflimide In 1,2-dichloro-ethane at 20 - 120℃; for 4h; Sealed tube;
61% With [Ru(p-cymene)Cl2]2; silver(I) acetate; silver(I) triflimide In 1,2-dichloro-ethane for 4h; Sealed tube; General procedure for the synthesis of products 4 and 5. General procedure: Chromones 1 (0.2mmol, 1 equiv) and maleimides 2 (0.5mmol, 2.5 equiv) were dissolved in a 12mL screw-capped tube with 2mL of DCE (0.1M). Then, [Ru(p-cymene)Cl2]2 (0.01mmol, 0.05 equiv), AgNTf2 (0.04mmol, 0.2 equiv), and AgOAc (0.6mmol, 3 equiv) were added to the reaction mixture at room temperature in air. The reaction mixture was allowed to warm up to 120°C in a heating mantle and stirred for 0.5-12h. After finishing the reaction, the reaction mixture was directly loaded on a silica gel column and purified with the petroleum ether/EtOAc mixture to provide the desired products 4 and 5.
61% With [Ru(p-cymene)Cl2]2; silver(I) acetate; silver(I) triflimide In 1,2-dichloro-ethane for 4h; Sealed tube; General procedure for the synthesis of products 4 and 5. General procedure: Chromones 1 (0.2mmol, 1 equiv) and maleimides 2 (0.5mmol, 2.5 equiv) were dissolved in a 12mL screw-capped tube with 2mL of DCE (0.1M). Then, [Ru(p-cymene)Cl2]2 (0.01mmol, 0.05 equiv), AgNTf2 (0.04mmol, 0.2 equiv), and AgOAc (0.6mmol, 3 equiv) were added to the reaction mixture at room temperature in air. The reaction mixture was allowed to warm up to 120°C in a heating mantle and stirred for 0.5-12h. After finishing the reaction, the reaction mixture was directly loaded on a silica gel column and purified with the petroleum ether/EtOAc mixture to provide the desired products 4 and 5.

 

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