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Product Details of [ 6479-18-1 ]

CAS No. :6479-18-1 MDL No. :MFCD01860250
Formula : C9H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :CHPVQLYVDDOWNT-UHFFFAOYSA-N
M.W : 160.17 Pubchem ID :351429
Synonyms :

Safety of [ 6479-18-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6479-18-1 ]

* 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 [ 6479-18-1 ]

[ 6479-18-1 ] Synthesis Path-Downstream   1~89

  • 1
  • [ 6479-18-1 ]
  • [ 31595-64-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 35percent H2O2, 5percent aq. NaOH / 5 h / 70 - 80 °C 2: POCl3 / 1.5 h / Heating 3: hydrazine hydrate / ethanol / 1 h / Heating
  • 2
  • [ 1196-57-2 ]
  • [ 74-88-4 ]
  • [ 6479-18-1 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In N,N-dimethyl-formamide at 20℃;
87% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;
80% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 40℃; for 5h;
34% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h; Schlenk technique; Inert atmosphere;
With sodium hydroxide In N,N-dimethyl-formamide at 20℃; 1 The reaction formula is as follows: In a 150mL round bottom flask were added quinoxaline-2(1H)-one (10mmol, 1.46g), methyl iodide (16mmol, 2.27g), sodium hydroxide (12mmol,) and 50mL dimethylformamide (DMF). ), stirred overnight at room temperature, and the reaction was detected by TLC. After the reaction is completed, add 30 mL of sodium chloride solution to the reaction solution, extract three times with 30 mL of ethyl acetate, combine the organic phases, wash three times with saturated ammonium chloride, dry with anhydrous magnesium sulfate, filter, and spin dry. Use petroleum ether and ethyl acetate (5:1) ratio as the eluent to pass through the column for purification, and dry to obtain 1-methylquinoxalin-2(1H)-one.

  • 3
  • [ 2620-05-5 ]
  • [ 6479-18-1 ]
  • (8S,9R,10S)-8,9,10-tribromo-1-methyl-1,4-diazaspiro[4.5]deca-3,6-dien-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / dimethyl sulfoxide / 20 °C 2: N-Bromosuccinimide / dichloromethane / 3 h / 20 °C / Irradiation
  • 4
  • [ 1196-57-2 ]
  • [ 6479-18-1 ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate In N,N-dimethyl-formamide at 20℃; 3 General procedure for the synthesis of the substrate (2b-2e) General procedure: A general procedure: To a stirred solution of quinoxalin-2(1H)-ones (3 mmol) in DMF (10 mL) was added the corresponding halide (1.6 eq.) and potassium carbonate (1.2 eq.) at room temperature. After disappearance of quinoxalin-2(1H)-ones, the resulting mixture was added with water, and extracted with ethyl acetate for three times. The combined organic layers were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel to obtain the desired product 2b to 2e.
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; 2.1 Preparation of substrates 1 General procedure: A mixture of o-phenylenediamine (5 mmol), ethyl 2-oxoacetate (6 mmol) and ethanol (20 mL) in a dried 50 mL round-bottom flask was stirred at reflux for 1 hour. After the completion (as indicated by TLC), the reaction mixture was filtered, washed with ethanol and then dried to give quinoxalinone 1'. Subsequently, A mixture of quinoxalinone 1', K2CO3 (1.2 equiv.), corresponding halogenoalkane (1.6 equiv.) and DMF (20 ml) in a dried 50 mL round-bottom flask was stirred at room temperature overnight. After the completion (as indicated by TLC), The mixture was then extracted with ethyl acetate and the collected organic layer was washed with brine, dried with MgSO4. The solvent was removed under reduced pressure, and the crude product was further purified by silica gel column chromatography (200-300 mesh silica gel, PE/EA = 5:1) to afford desired substrates 1.
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
With methylene chloride; potassium carbonate In N,N-dimethyl-formamide at 20℃;

  • 5
  • [ 6479-18-1 ]
  • [ 5720-07-0 ]
  • 3-(4-methoxyphenyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With oxygen; palladium diacetate; 1,7-phenanthroline In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere;
85% With manganese(III) triacetate dihydrate In acetonitrile at 120℃; for 12h; Inert atmosphere; General procedure General procedure: A sealed tube was charged with quinoxalin-2(1H)-one (1, 0.625mmol) and CH3CN (5 mL) and the solution was purged with argongas for 30 min and then Mn(OAc)3*2H2O (1.873 mmol) and arylboronicacid (2, 0.745 mmol) were added. After removal of oxygenby argon gas, the reaction vessel was sealed with a Teflon screw.The reaction was stirred at 120 C for 12 h. The resulting suspensionwas cooled to room temperature and diluted with ethyl acetate.The organic layer was filtered through Whatman filter paperand evaporated under reduced pressure. The residue was purifiedby flash chromatography over silica gel to afford the desiredproduct.
77% With dipotassium peroxodisulfate; potassium carbonate In water at 80℃; for 2h;
71% With dipotassium peroxodisulfate; eosin Y disodium salt In water at 20℃; for 12h; Irradiation; Green chemistry; 1.2 General procedure for the synthesis of 3-arylquinoxalin-2(1H)-ones (3) General procedure: Aryl boronic acid (2) should be portionwise added into a mixture of quinoxalinones (1) (0.2 mmol), K2S2O8 (1.5 equiv.), Eosin Y (3 mol %) and H2O (2 mL) in a 10 mL tube under blue LED for 12 hours. After completion of the reaction, as monitored by TLC, The mixture was then extracted with EtOAc and the collected organic layer was dried with MgSO4. The solvent was evaporated in vacuum, and the obtained residue was further purified by silica gel column chromatography (200-300 mesh silica gel, PE/EA = 4:1).
51% With oxygen; trifluoroacetic acid In acetonitrile at 120℃; for 16h; chemoselective reaction; General procedure for the arylation of quinoxalin-2(1H)-ones with arylboronic acids General procedure: To a 15 mL tube was charged with 1a (0.2 mmol), 5 (0.4 mmol), CF3CO2H (25 mol%), and CH3CN (2 mL). The tube was evacuated and backfilled with O2 for three times, and heated to 120 oC in the heating block for 16 h. The reaction mixture was then quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure. The crude product was further purified by silica gel column chromatography (200-300 mesh silica gel, PE/EA = 4:1) to afford product 6.

  • 6
  • [ 6479-18-1 ]
  • [ 156641-98-4 ]
  • 3-(6-methoxynaphthalen-2-yl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With oxygen; palladium diacetate; 1,7-phenanthroline In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere;
  • 7
  • [ 6479-18-1 ]
  • [ 10365-98-7 ]
  • 3-(3-methoxyphenyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With manganese(III) triacetate dihydrate In acetonitrile at 120℃; for 12h; Inert atmosphere; General procedure General procedure: A sealed tube was charged with quinoxalin-2(1H)-one (1, 0.625mmol) and CH3CN (5 mL) and the solution was purged with argongas for 30 min and then Mn(OAc)3*2H2O (1.873 mmol) and arylboronicacid (2, 0.745 mmol) were added. After removal of oxygenby argon gas, the reaction vessel was sealed with a Teflon screw.The reaction was stirred at 120 C for 12 h. The resulting suspensionwas cooled to room temperature and diluted with ethyl acetate.The organic layer was filtered through Whatman filter paperand evaporated under reduced pressure. The residue was purifiedby flash chromatography over silica gel to afford the desiredproduct.
80% With oxygen; palladium diacetate; 1,7-phenanthroline In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere;
72% With dipotassium peroxodisulfate; eosin Y disodium salt In water at 20℃; for 12h; Irradiation; Green chemistry; 1.2 General procedure for the synthesis of 3-arylquinoxalin-2(1H)-ones (3) General procedure: Aryl boronic acid (2) should be portionwise added into a mixture of quinoxalinones (1) (0.2 mmol), K2S2O8 (1.5 equiv.), Eosin Y (3 mol %) and H2O (2 mL) in a 10 mL tube under blue LED for 12 hours. After completion of the reaction, as monitored by TLC, The mixture was then extracted with EtOAc and the collected organic layer was dried with MgSO4. The solvent was evaporated in vacuum, and the obtained residue was further purified by silica gel column chromatography (200-300 mesh silica gel, PE/EA = 4:1).
  • 8
  • [ 6479-18-1 ]
  • [ 1679-18-1 ]
  • 3-(4-chlorophenyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With manganese(III) triacetate dihydrate In acetonitrile at 120℃; for 12h; Inert atmosphere; General procedure General procedure: A sealed tube was charged with quinoxalin-2(1H)-one (1, 0.625mmol) and CH3CN (5 mL) and the solution was purged with argongas for 30 min and then Mn(OAc)3*2H2O (1.873 mmol) and arylboronicacid (2, 0.745 mmol) were added. After removal of oxygenby argon gas, the reaction vessel was sealed with a Teflon screw.The reaction was stirred at 120 C for 12 h. The resulting suspensionwas cooled to room temperature and diluted with ethyl acetate.The organic layer was filtered through Whatman filter paperand evaporated under reduced pressure. The residue was purifiedby flash chromatography over silica gel to afford the desiredproduct.
67% With dipotassium peroxodisulfate; potassium carbonate In water at 80℃; for 3h;
57% With dipotassium peroxodisulfate; eosin Y disodium salt In water at 20℃; for 12h; Irradiation; Green chemistry; 1.2 General procedure for the synthesis of 3-arylquinoxalin-2(1H)-ones (3) General procedure: Aryl boronic acid (2) should be portionwise added into a mixture of quinoxalinones (1) (0.2 mmol), K2S2O8 (1.5 equiv.), Eosin Y (3 mol %) and H2O (2 mL) in a 10 mL tube under blue LED for 12 hours. After completion of the reaction, as monitored by TLC, The mixture was then extracted with EtOAc and the collected organic layer was dried with MgSO4. The solvent was evaporated in vacuum, and the obtained residue was further purified by silica gel column chromatography (200-300 mesh silica gel, PE/EA = 4:1).
40% With oxygen; palladium diacetate; 1,7-phenanthroline In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere;

  • 9
  • [ 6479-18-1 ]
  • [ 7163-50-0 ]
  • 1-methyl-3-(4-methylbenzoyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With air In water; 1,2-dichloro-ethane at 20℃; Irradiation; Green chemistry; regioselective reaction;
81% With Acridine Red In 1,2-dichloro-ethane at 20℃; for 8h; Irradiation; 2 Example 2 At room temperature, add 1a (0.1 mmol), p-methylacetophenone acid 2b (0.2 mmol) in a 15 mL reaction tube,Photocatalyst acridine red (0.001 mmol), 1,2 dichloroethane 2mL, mix well,Then, under the irradiation of a 3w blue LED lamp, the reaction was stirred in the air for 8h.After the completion of the reaction was detected by TLC, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent.The crude product was obtained, and then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 5: 1.Flash column chromatography on a silica gel column yielded the 3ab product of this example as a 22.5 mg yellow solid with a yield of 81%.
80% With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 100℃; for 3h; Sealed tube; chemoselective reaction;
80% With 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane at 23℃; for 36h; Irradiation;
73% With [bis(acetoxy)iodo]benzene In water at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;

  • 10
  • [ 6479-18-1 ]
  • [ 7099-91-4 ]
  • 1-methyl-3-(4-methoxybenzoyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With [bis(acetoxy)iodo]benzene In water at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;
86% With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 100℃; for 3h; Sealed tube; chemoselective reaction;
63% With Acridine Red In 1,2-dichloro-ethane at 20℃; for 8h; Irradiation; 3 Example 3 At room temperature, 1a (0.1mmol), p-methoxyacetophenone acid 2c (0.2mmol) were sequentially added to a 15mL reaction tube.Photocatalyst acridine red (0.001 mmol), 1,2 dichloroethane 2mL, mix well,Then, under the irradiation of a 3w blue LED lamp, the reaction was stirred in the air for 8h.After the completion of the reaction was detected by TLC, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent.The crude product was obtained, and then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 5: 1.Flash column chromatography on a silica gel column gave the 3ac product of this example as a yellow solid, 18.5 mg, with a yield of 63%.
62% With air In water; 1,2-dichloro-ethane at 20℃; Irradiation; Green chemistry; regioselective reaction;

  • 11
  • [ 6479-18-1 ]
  • [ 7099-88-9 ]
  • 1-methyl-3-(4-chlorobenzoyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With Acridine Red; In 1,2-dichloro-ethane; at 20℃; for 8h;Irradiation; At room temperature, in a 15 mL reaction tube, 1a (0.1 mmol), p-chloroacetophenic acid 2e (0.2 mmol) were sequentially added.Photocatalyst acridine red (0.001 mmol), 1,2 dichloroethane 2mL, mix well,Then, under the irradiation of a 3w blue LED lamp, the reaction was stirred in the air for 8h.After the completion of the reaction was detected by TLC, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent.The crude product was obtained, and then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 5: 1.Flash column chromatography on a silica gel column gave the 3ae product of this example as a yellow solid, 24.5 mg, with a yield of 82%.
  • 12
  • [ 6479-18-1 ]
  • [ 7099-87-8 ]
  • 1-methyl-3-(4-bromobenzoyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With air In water; 1,2-dichloro-ethane at 20℃; Irradiation; Green chemistry; regioselective reaction;
72% With [bis(acetoxy)iodo]benzene In water at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;
63% With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 100℃; for 3h; Sealed tube; chemoselective reaction;
63% With Acridine Red In 1,2-dichloro-ethane at 20℃; for 8h; Irradiation; 7 Example 7 At room temperature, 1a (0.1 mmol) and p-bromoacetophenone acid (2 g (0.2 mmol)) were sequentially added to a 15 mL reaction tube.Photocatalyst acridine red (0.001 mmol), 1,2 dichloroethane 2mL, mix well,Then, under the irradiation of a 3w blue LED lamp, the reaction was stirred in the air for 8h. After the completion of the reaction was detected by TLC, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent.The crude product was obtained, and then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 5: 1.Flash column chromatography on a silica gel column yielded the 3ag product of this example as a 21.6 mg yellow solid with a yield of 63%.

  • 13
  • [ 6479-18-1 ]
  • [ 26767-16-8 ]
  • 1-methyl-3-(2-bromobenzoyl)quinoxalin-2(1H)-one [ No CAS ]
  • 14
  • [ 6479-18-1 ]
  • [ 62-53-3 ]
  • [ 2048-37-5 ]
YieldReaction ConditionsOperation in experiment
81% With tert.-butylnitrite; methanesulfonic acid In acetone at 20℃; for 1.5h; Schlenk technique;
80% Stage #1: aniline With tert.-butylnitrite In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Green chemistry; Stage #2: 1,2-dihydro-1-methylquinoxalin-2-one In acetonitrile at 20℃; for 48h; Inert atmosphere; Schlenk technique; Green chemistry; Method A for The Synthesis of 3a; 3b; 3c; 3d; 3f; 3g; 3h; 3i; 3j; 3k; 3l; 3t; 3x; 3z; 3aa; 3ab. General procedure: To a 25mL round bottle was added corresponding aryl aniline (4.0 equiv.) and 1.0 mL of anhydrous CH3CN, thentBuONO (6.0 equiv.) was added dropwise via syringe in an ice bath, followed by washing the syringe with CH3CN(0.5 mL x 2). After addition, the mixture was warmed and continued to stir at rt for 0.5 h (preparing in situArN2OBut). Then the ArN2OBut in CH3CN was transferred into an oven-dried Schlenk tube (25 mL) charged withcorresponding quinoxalin-2(1H)-one (1, 0.3 mmol, 1.0 equiv.), followed by washing the bottle with CH3CN (0.5mL x 2). The Schlenk tube was exchanged adequately by N2. Then, the mixture was stirred for 48 h at rt. The finialmixture was diluted by ethyl acetate and filtered through a pad of silica. The filtrate was concentrated underreduced pressure and the residue was purified by self-prepared silica plate (petroleum ether/ethyl acetate: 20/1 to10/1) to afford the desired product 3 as yellow or orange solid (3d:orange colloid).
72% Stage #1: aniline With hydrogen tetrafluoroborate; tert.-butylnitrite In ethanol; water monomer at 0 - 20℃; for 1.08333h; Stage #2: 1,2-dihydro-1-methylquinoxalin-2-one With barium titanate In acetonitrile for 6h; Milling;
  • 15
  • [ 6479-18-1 ]
  • [ 371-40-4 ]
  • [ 1057224-07-3 ]
YieldReaction ConditionsOperation in experiment
78% With tert.-butylnitrite; methanesulfonic acid In acetone at 20℃; for 1.5h; Schlenk technique;
75% Stage #1: 4-fluoroaniline With hydrogen tetrafluoroborate; tert.-butylnitrite In ethanol; water monomer at 0 - 20℃; for 1.08333h; Stage #2: 1,2-dihydro-1-methylquinoxalin-2-one With barium titanate In acetonitrile for 6h; Milling;
70% Stage #1: 4-fluoroaniline With tert.-butylnitrite In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Green chemistry; Stage #2: 1,2-dihydro-1-methylquinoxalin-2-one In acetonitrile at 20℃; for 48h; Inert atmosphere; Schlenk technique; Green chemistry; Method A for The Synthesis of 3a; 3b; 3c; 3d; 3f; 3g; 3h; 3i; 3j; 3k; 3l; 3t; 3x; 3z; 3aa; 3ab. General procedure: To a 25mL round bottle was added corresponding aryl aniline (4.0 equiv.) and 1.0 mL of anhydrous CH3CN, thentBuONO (6.0 equiv.) was added dropwise via syringe in an ice bath, followed by washing the syringe with CH3CN(0.5 mL x 2). After addition, the mixture was warmed and continued to stir at rt for 0.5 h (preparing in situArN2OBut). Then the ArN2OBut in CH3CN was transferred into an oven-dried Schlenk tube (25 mL) charged withcorresponding quinoxalin-2(1H)-one (1, 0.3 mmol, 1.0 equiv.), followed by washing the bottle with CH3CN (0.5mL x 2). The Schlenk tube was exchanged adequately by N2. Then, the mixture was stirred for 48 h at rt. The finialmixture was diluted by ethyl acetate and filtered through a pad of silica. The filtrate was concentrated underreduced pressure and the residue was purified by self-prepared silica plate (petroleum ether/ethyl acetate: 20/1 to10/1) to afford the desired product 3 as yellow or orange solid (3d:orange colloid).
  • 16
  • [ 6479-18-1 ]
  • [ 106-47-8 ]
  • 3-(4-chlorophenyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tert.-butylnitrite; methanesulfonic acid In acetone at 20℃; for 1.5h; Schlenk technique;
71% Stage #1: 4-chloro-aniline With tert.-butylnitrite In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Green chemistry; Stage #2: 1,2-dihydro-1-methylquinoxalin-2-one In acetonitrile at 20℃; for 48h; Inert atmosphere; Schlenk technique; Green chemistry; Method A for The Synthesis of 3a; 3b; 3c; 3d; 3f; 3g; 3h; 3i; 3j; 3k; 3l; 3t; 3x; 3z; 3aa; 3ab. General procedure: To a 25mL round bottle was added corresponding aryl aniline (4.0 equiv.) and 1.0 mL of anhydrous CH3CN, thentBuONO (6.0 equiv.) was added dropwise via syringe in an ice bath, followed by washing the syringe with CH3CN(0.5 mL x 2). After addition, the mixture was warmed and continued to stir at rt for 0.5 h (preparing in situArN2OBut). Then the ArN2OBut in CH3CN was transferred into an oven-dried Schlenk tube (25 mL) charged withcorresponding quinoxalin-2(1H)-one (1, 0.3 mmol, 1.0 equiv.), followed by washing the bottle with CH3CN (0.5mL x 2). The Schlenk tube was exchanged adequately by N2. Then, the mixture was stirred for 48 h at rt. The finialmixture was diluted by ethyl acetate and filtered through a pad of silica. The filtrate was concentrated underreduced pressure and the residue was purified by self-prepared silica plate (petroleum ether/ethyl acetate: 20/1 to10/1) to afford the desired product 3 as yellow or orange solid (3d:orange colloid).
71% Stage #1: 4-chloro-aniline With hydrogen tetrafluoroborate; tert.-butylnitrite In ethanol; water monomer at 0 - 20℃; for 1.08333h; Stage #2: 1,2-dihydro-1-methylquinoxalin-2-one With barium titanate In acetonitrile for 6h; Milling;
  • 17
  • [ 6479-18-1 ]
  • cyclobutanone oxime ester [ No CAS ]
  • 4-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)-3-phenylbutanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With iron(II) acetylacetonate In acetonitrile at 100℃; for 18h; Sealed tube; Inert atmosphere;
77% With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In N,N-dimethyl-formamide at 20℃; for 18h; Glovebox; Irradiation; 4. General procedure for the visible-light-driven cyanoalkylation of quinoxalinone General procedure: Quinoxalin-2(1H)-one 1a (0.2 mmol), cyclobutanone O-acyl oxime 2a (0.21 mmol, 1.05 equiv), photocatalyst (1 mol%) and DMF (1.0 mL) was added to 10 mL quartz reaction tube equipped with a magnetic stir bar in a glove box. The tube was sealed with a Teflon screw cap, and the reaction mixture was stirred at room temperature under 5W blue-light irradiation (460-465 nm) for 18 h. Then the reaction mixture was diluted with DCM and washed with brine; the organic layer was evaporated to dryness under the reduced pressure. The crude residue was purified by column chromatography on silica gel (0 to 50% ethyl acetate in hexanes) to yield product 3a.
52% With tetrahydroxydiboron In N,N-dimethyl acetamide at 20℃; for 16h;
  • 18
  • [ 6479-18-1 ]
  • [ 120-14-9 ]
  • 3-(3,4-dimethoxybenzoyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tert-Butyl peroxybenzoate In ethyl acetate at 80℃; for 5h; 6 Preparation of 1-methyl-3-(3,4-dimethoxybenzoyl) quinoxalin-2-one derivative with R1=-CH3, R2=-H, when Add 1-methylquinoxalin-2-one (0.2mmol, 32.0mg) and 3,4-dimethoxybenzaldehyde (0.36mmol, 57.6mg) into a 25mL round bottom flask, Then add tert-butyl peroxybenzoate (0.8mmol, 155.2 mg), and finally add 2mL ethyl acetate as the solvent. React at 80°C for 5h; after the reaction is over, add 10mL ethyl acetate to the reaction solution, Washed twice with 20 mL of saturated brine; the organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure and then separated and purified by column chromatography (eluent: ethyl acetate/petroleum ether = 1/5) to obtain 0.058 g of a colorless solid. The yield was 90.0%.
82% With tert.-butylhydroperoxide In 1,2-dichloro-ethane at 70℃; for 5h; Schlenk technique; regioselective reaction;
  • 19
  • [ 6479-18-1 ]
  • [ 1135-12-2 ]
  • 3-(4-benzylphenyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% General procedure: To a 25mL round bottle was added corresponding aryl aniline (4.0 equiv.) and 2.0 mL of anhydrous CH3CN, thentBuONO (6.0 equiv.) was added dropwise via syringe in an ice bath, followed by washing the syringe with CH3CN(0.5 mL x 2). After addition, the mixture was warmed and continued to stir at rt for 0.5 h (preparing in situArN2OBut). Then the ArN2OBut in CH3CN was transferred into an oven-dried Schlenk tube (25 mL) charged withcorresponding quinoxalin-2(1H)-one (1, 0.3 mmol, 1.0 equiv.), followed by washing the bottle with CH3CN (0.5mL x 2). The Schlenk tube was exchanged adequately by N2. Then, the mixture was stirred for 48 h at rt. The finialmixture was diluted by ethyl acetate and filtered through a pad of silica. The filtrate was concentrated underreduced pressure and the residue was purified by self-prepared silica plate (petroleum ether/ethyl acetate: 20/1 to10/1) to afford the desired product 3 as yellow or orange solid.
  • 20
  • [ 6479-18-1 ]
  • [ 139-59-3 ]
  • 1-methyl-3-(4-phenoxyphenyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: 4-phenoxyanilin With tert.-butylnitrite In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Green chemistry; Stage #2: 1-methyl-2(1H)-quinoxalinone In acetonitrile at 20℃; for 48h; Inert atmosphere; Schlenk technique; Green chemistry; Typical Procedure A 25 mL round bottle was charged with 4-phenoxyaniline (4.0equiv) and anhyd MeCN (1.0 mL). t-BuONO (6.0 equiv) wasadded dropwise from a syringe cooled in an ice bath, and thesyringe was then rinsed through with MeCN (2 × 0.5 mL). Whenthe addition was complete, the mixture was warmed to r.t. andstirred for 0.5 h to form 4-PhOC6H4N=NOBu-t in situ. Themixture was then transferred to an oven-dried 25 mL Schlenktube containing 1-methylquinoxalin-2(1H)-one (1a; 0.3 mmol,1.0 equiv). The bottle was rinsed with MeCN (2 × 0.5 mL), whichwas also transferred into the Schlenk tube. The atmosphere inthe Schlenk tube was then exchanged adequately by N2 and themixture was stirred for 48 h at r.t. The final mixture was dilutedwith EtOAc and filtered through a pad of silica gel. The filtratewas concentrated under reduced pressure and the residue waspurified by TLC [self-prepared silica gel plates, PE-EtOAc(20:1 to 10:1)] to give an orange solid; yield: 70 mg (71%); mp102-104 °C. 1H NMR (400 MHz, CDCl3): δ = 8.40-8.33 (m, 2 H),7.93 (dd, J = 8.0, 1.6 Hz, 1 H), 7.60-7.53 (m, 1 H), 7.42-7.31 (m, 4H), 7.15 (t, J = 7.4 Hz, 1 H), 7.11-7.07 (m, 4 H), 3.78 (s, 3 H). 13CNMR (101 MHz, CDCl3): δ = 159.50, 156.56, 154.80, 153.16,133.27, 133.16, 131.56, 130.97, 130.32, 130.14, 129.92, 123.88,123.80, 119.61, 117.89, 113.64, 29.37. HRMS (ESI): m/z [M + H]+calcd for C21H17N2O2: 329.1285; found: 329.1276.
  • 21
  • [ 6479-18-1 ]
  • [ 94839-07-3 ]
  • 3-(benzo[d][1,3]dioxol-5-yl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With manganese(III) triacetate dihydrate; In acetonitrile; at 120℃; for 12h;Inert atmosphere; General procedure: A sealed tube was charged with quinoxalin-2(1H)-one (1, 0.625mmol) and CH3CN (5 mL) and the solution was purged with argongas for 30 min and then Mn(OAc)3*2H2O (1.873 mmol) and arylboronicacid (2, 0.745 mmol) were added. After removal of oxygenby argon gas, the reaction vessel was sealed with a Teflon screw.The reaction was stirred at 120 C for 12 h. The resulting suspensionwas cooled to room temperature and diluted with ethyl acetate.The organic layer was filtered through Whatman filter paperand evaporated under reduced pressure. The residue was purifiedby flash chromatography over silica gel to afford the desiredproduct.
69% With dipotassium peroxodisulfate; eosin Y disodium salt; In water; at 20℃; for 12h;Irradiation; Green chemistry; General procedure: Aryl boronic acid (2) should be portionwise added into a mixture of quinoxalinones (1) (0.2 mmol), K2S2O8 (1.5 equiv.), Eosin Y (3 mol %) and H2O (2 mL) in a 10 mL tube under blue LED for 12 hours. After completion of the reaction, as monitored by TLC, The mixture was then extracted with EtOAc and the collected organic layer was dried with MgSO4. The solvent was evaporated in vacuum, and the obtained residue was further purified by silica gel column chromatography (200-300 mesh silica gel, PE/EA = 4:1).
  • 22
  • [ 6479-18-1 ]
  • [ 2016-57-1 ]
  • 3-(decylamino)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With eosin In tetrahydrofuran at 20℃; for 16h; Irradiation;
71% With water soluable eosin In tetrahydrofuran for 18h; Irradiation; 22 example 22 At room temperature, quinoxaline-2(1H)-one 1a (0.2 mmol), 2 phenethylamine (0.4 mmol), water-soluble eosin (0.002 mmol), and tetrahydrofuran 2 mL were added in a 15 mL reaction tube. Then, under a 3 W (Watt) blue LED lamp, the reaction was stirred for 18 h. After the completion of the reaction by TLC, 2 mL of water was added, and then extracted with ethyl acetate for 3 times. The extracts were combined, and the extract was dried over anhydrous sodium sulfate, and then the mixture was concentrated under vacuum (0.08 Mpa) Solvent, the crude product was obtained, and then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 3:1, and column chromatography on silica gel to obtain 3-aminoquinoxaline-2 (1H). The ketone product 3ah was 44.7 mg as a white solid, yield 71%.
  • 23
  • [ 109-99-9 ]
  • [ 6479-18-1 ]
  • 1-methyl-3-(tetrahydrofuran-2-yl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With eosin Y disodium salt at 27℃; for 24h; Irradiation; Green chemistry;
90% With 1,4-diaza-bicyclo[2.2.2]octane; tert.-butylhydroperoxide; 4,5,6,7-tetrachloro-2′,4′,5′,7′-tetraiodofluorescein disodium salt at 25℃; for 24h; Irradiation; 1 At 25 ° C,In a 15 mL reaction tube,1-methylquinoxaline-2 (1H)-one 1a (0.2 mmol,), Bengal rose red (0.002 mmol),Triethylenediamine (0.2mmol),Tert-butyl alcohol peroxide (0.2 mmol),THF 2a (12 mmol, 1 mL),well mixed,Then under the illumination of a 3w blue LED light,The reaction was stirred for 24 h.After detecting by TLC until the reaction is completed,The reaction solution was concentrated under reduced pressure in vacuo (0.08Mpa) to solvent.Obtaining a crude product,Then rinse with a mixed eluent of 3:1 by volume of petroleum ether and ethyl acetate.Silica gel column flash column chromatography,This example was obtained as 1-methyl-3-(tetrahydrofuran-2-a quinoxaline-2(1H)-one product 3aa,Is a colorless liquid 41.4mg,The yield was 90%.
89% With 9,10-phenanthrenequinone In 1,2-dichloro-ethane at 20℃; for 16h; Irradiation; regioselective reaction;
56% With cerium(III) trichloride; 2,2,2-trifluoroethanol; tetra-n-butyl-ammonium chloride In acetonitrile at 20℃; for 9h; Irradiation;
52% With di-tert-butyl peroxide In neat (no solvent) at 130℃; for 4h; Sealed tube;

  • 24
  • [ 6479-18-1 ]
  • [ 423-39-2 ]
  • [ 2489-86-3 ]
  • C26H19F9N2O [ No CAS ]
  • 25
  • [ 6479-18-1 ]
  • [ 1968-40-7 ]
  • [ 423-39-2 ]
  • C20H19F9N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 25℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;
  • 26
  • [ 6479-18-1 ]
  • C19H16F5NO2 [ No CAS ]
  • [ 2979-69-3 ]
  • 1-methyl-3-(2-methyl-5-oxo-5-phenylpentan-2-yl)quinoxalin-2(1H)-one [ No CAS ]
  • 27
  • [ 6479-18-1 ]
  • [ 82031-32-1 ]
  • 7-bromo-4'-methyl-2H-[1,2'-biquinoxaline]-2,3'(4'H)-dione [ No CAS ]
  • 28
  • [ 6479-18-1 ]
  • [ 4053-34-3 ]
  • 1-methyl-3-(6-methyl-2-oxoquinolin-1(2H)-yl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With copper diacetate; potassium carbonate In N,N-dimethyl acetamide at 120℃; for 8h;
  • 29
  • [ 6479-18-1 ]
  • [ 99465-10-8 ]
  • 3-(7-bromo-2-oxoquinolin-1(2H)-yl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
  • 30
  • [ 6479-18-1 ]
  • [ 22614-75-1 ]
  • 3-(6-fluoro-2-oxoquinolin-1(2H)-yl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With copper diacetate; potassium carbonate In N,N-dimethyl acetamide at 120℃; for 8h;
  • 31
  • [ 6479-18-1 ]
  • [ 1003-56-1 ]
  • 1-methyl-3-(3-methyl-2-oxopyridin-1(2H)-yl)quinoxalin-2(1H)-one [ No CAS ]
  • 32
  • [ 6479-18-1 ]
  • [ 359-13-7 ]
  • 3-(2,2-difluoroethoxy)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With bis-[(trifluoroacetoxy)iodo]benzene In chloroform at 25℃; for 2h; 2 Example 2: 1-Methyl-2(1H)-quinoxalinone (1.60 g, 10 mmol), bis(trifluoroacetic acid) iodobenzene (8.60 g, 20 mmol),Difluoroethanol (3.28 g, 40 mmol) was added to the reaction flask, dissolved in chloroform (20 mL), and stirred at 25 ° C for 2 hours.After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution (10 mL) was added to quench the reaction, and the mixture was stirred and allowed to stand for separation.The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated.The crude product was recrystallized from ethyl acetate/petroleum ether (v/v = 1:1).1.90 g of a white solid was obtained in a yield of 79%.
73% With Eosin Y; oxygen at 20℃; for 24h; Irradiation; Green chemistry; regioselective reaction;
72% With bis-[(trifluoroacetoxy)iodo]benzene In neat (no solvent) at 35℃; for 1h;
  • 33
  • [ 6479-18-1 ]
  • [ 461-18-7 ]
  • 1-methyl-3-(4,4,4-trifluorobutoxy)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With bis-[(trifluoroacetoxy)iodo]benzene In neat (no solvent) at 35℃; for 1h;
78% With Eosin Y; oxygen at 20℃; for 24h; Irradiation; Green chemistry; regioselective reaction;
76% With bis-[(trifluoroacetoxy)iodo]benzene In chloroform at 25℃; for 2h; 5 Example 5: 1-methyl-2(1H)-quinoxalinone (1.60 g, 10 mmol),Di(trifluoroacetic acid) iodobenzene (8.60 g, 20 mmol), trifluorobutanol (5.12 g, 40 mmol) was added to the reaction flask.Add chloroform (20 mL) to dissolve, and stir the reaction at 25 ° C for 2 hours.After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution (10 mL) was added to quench the reaction, and the mixture was stirred and allowed to stand for separation.The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated.The crude product was recrystallized from ethyl acetate/petroleum ether (v/v = 1:1).Obtained 2.17g of a white solid.The yield was 76%.
  • 34
  • [ 6479-18-1 ]
  • ethyl 3-(((4-(trifluoromethyl)benzoyl)oxy)imino)cyclobutane-1-carboxylate [ No CAS ]
  • ethyl 3-cyano-2-((4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)-methyl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With eosin y In dichloromethane at 20℃; Irradiation; Inert atmosphere; Green chemistry;
81% With tetrabutylammonium tetrafluoroborate In N,N-dimethyl acetamide at 20℃; for 36h; Electrolysis; Green chemistry; 5. General Procedure for Electrolysis General procedure: An oven-dried 20 mL undivided bottle was equipped with two graphite sheet electrodes (10 mm× 100 mm × 3 mm). The corresponding quinoxalin-2(1H)-one (48.0 mg, 0.3 mmol, 1.0 equiv.), thecyclobutanone oxime ester (154.2 mg, 0.6 mmol, 2.0 equiv.) and nBu4NBF4 (197.4 mg, 0.6 mmol,42.0 equiv.) was added into the undivided cell. And then DMA (5 mL) was added. The reactionmixture was stirred and electrolyzed at a constant-voltage of 3.0 V under room temperature for 36h. Later the brine was added, the solvent was extracted three times with EtOAc. The combinedorganic layers were firstly washed with saturated NaHCO3 then with brine, dried over anhydrousNa2SO4, filtered and then concentrated in vacuum. The pure product was obtained by flash columnchromatography on silica gel (petroleum ether/ethyl acetate = 3/1).
  • 35
  • [ 6479-18-1 ]
  • [ 802294-64-0 ]
  • [ 13494-42-3 ]
YieldReaction ConditionsOperation in experiment
90% With tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate; [bis(acetoxy)iodo]benzene In chloroform at 25℃; for 8h; Microwave irradiation; Photolysis; 1 The specific reaction conditions are as follows odine diacetate (10 mmol), propionic acid (20 mmol) was added to a round bottom flask, dissolved in 25 ml of chloroform, and concentrated to dryness under reduced pressure at 50 ° C to obtain iodobenzene 2b dipropionate, which was used without purification. In the next step.In a 10 mL reaction tube, 1-methylquinoxaline-2(1Η)-one la (0.2 mmol), iodobenzene 2b (0.44 mmol), Ru(bpy) 3C12 were added in sequence at 25 ° C. · 6H20 (0.002mmol), PEG-200 (lmL), mixed evenly, and then stirred under a 3w blue LED lamp for 8h. After completion of the reaction by TLC, the mixture was extracted with cyclopentyl methyl ether (2 ml of X 3 ), and the extract was taken and concentrated in vacuo at 50 ° C until solvent was obtained to obtain crude product, and then oil was used in a volume ratio of 2:1. The ether and ethyl acetate mixed eluent was washed and flash column chromatography on silica gel to obtain 3-ethyl-1-methylquinoxaline-2(1H)-one product 4ab in the present example as a white solid 33.8 mg The yield is 90%.
73% With tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate In dimethyl sulfoxide at 20℃; for 8h; Schlenk technique; Irradiation; regioselective reaction;
72% With cerium(III) trichloride; 1,1,1-trichloroethanol; tetra-n-butyl-ammonium chloride In acetonitrile at 20℃; for 12h; Irradiation;
72% With cerium(III) trichloride; 1,1,1-trichloroethanol; [bis(acetoxy)iodo]benzene; tetra-n-butyl-ammonium chloride In acetonitrile at 20℃; for 12h; Irradiation;
42% With cerium(III) trichloride; potassium-t-butoxide In acetonitrile for 24h; Sealed tube; Irradiation;

  • 36
  • [ 6479-18-1 ]
  • [ 75-98-9 ]
  • 3-(tert-butyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With cerium(III) trichloride; potassium-t-butoxide In acetonitrile for 24h; Sealed tube; Irradiation;
86% With ammonium peroxodisulphate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation; General procedure for the prepration of 3- alkylquinoxalin-2(1H)-ones General procedure: To a solution of quinoxalin-2(1H)-ones 1 (0.3 mmol) and aliphatic acid 2 (0.75 mmol) in DMSO (3 mL) was added (NH4)2S2O8 (0.9 mmol). The reaction mixture was stirred at room temperature under the irradiation of 10 W blue LED lamps (440-445 nm) under N2 atmosphere conditions. The progress of the reaction was monitored by TLC. The reaction typically took within 24 hours. After completion, water (10mL) was added and the mixture was extracted with EtOAc (10 mL× 3), the solvent was then removed under vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired products 3.
85% With tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate; [bis(acetoxy)iodo]benzene In chloroform at 25℃; for 8h; Microwave irradiation; Photolysis; 4 The specific reaction conditions are as follows To the round bottom flask was added iodobenzene diacetate (10 mmol), tert-butyric acid (20 mmol), dissolved in 25 ml of chloroform, and concentrated to dryness under reduced pressure at 50 ° C to give 2-bromo-t-butyric acid, without purification. Used directly in the next step.1-Methylquinoxaline-2(1Η)-one la (0.2 mmol), diamantanecarboxylic acid iodobenzene 2 g (0.44 mmol), Ru(bpy), were sequentially added to a 10 mL reaction tube at 25 °C. 3CI2 * 6Η2Ο (0.002mmol), PEG-200 (lmL), evenly mixed,After the irradiation with a 3w blue LED lamp, the reaction was stirred for 8 hours. After detection by TLC until completion of the reaction, cyclopentyl methyl ether (2 ml X 3) was added.Extraction, taking the upper extract, and concentrating in vacuo at 50 ° C until no solvent to obtain a crude product, then using a petroleum ether in a volume ratio of 2:1The mixture was washed with an ethyl acetate mixed eluent and flash column chromatography on silica gel to give 1-methyl-3-adamantylquinoxaline-2 (1H)-one product 4ag as a white solid 48.8 mg. The yield was 83%.
70% With cerium(III) trichloride; 1,1,1-trichloroethanol; tetra-n-butyl-ammonium chloride In acetonitrile at 20℃; for 12h; Irradiation;
70% With cerium(III) trichloride; 1,1,1-trichloroethanol; [bis(acetoxy)iodo]benzene; tetra-n-butyl-ammonium chloride In acetonitrile at 20℃; for 12h; Irradiation;
63% With tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate In dimethyl sulfoxide at 20℃; for 10h; Schlenk technique; Irradiation; regioselective reaction;

  • 37
  • [ 6479-18-1 ]
  • [ 3302-10-1 ]
  • 1-methyl-3-(2,4,4-trimethylpentyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tris(bipyridine)ruthenium(II) dichloride hexahydrate In dimethyl sulfoxide at 20℃; for 9h; Schlenk technique; Irradiation; regioselective reaction;
  • 38
  • [ 6479-18-1 ]
  • [ 98-89-5 ]
  • 3-cyclohexyl-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate; phenyl-λ3-iodanediyl dicyclohexanecarboxylate In chloroform at 25℃; for 8h; Microwave irradiation; Photolysis; 1-16; 2 The specific reaction conditions are as follows Iodine diacetate (10 mmol), cyclohexylcarboxylic acid (20 mmol) was added to a round bottom flask, dissolved in 25 ml of chloroform, and concentrated to dryness under reduced pressure at 50 ° C to give 2b of cyclohexanecarboxylic acid. , used directly in the next reaction.In a 10 mL reaction tube, compound la (0.2 mmol), cyclohexanecarboxylic acid iodobenzene 2a (0.44 mmol), photocatalyst, solvent (1 mL) were mixed sequentially at 25 ° C, and then mixed in 3w blue LED. The reaction was stirred for 8 h under the irradiation of a lamp. After completion of the reaction by TLC, the mixture was extracted with cyclopentyl methyl ether (2 ml of X 3 ), and the extract was taken and concentrated in vacuo at 50 ° C until solvent was obtained to obtain crude product, and then oil was used in a volume ratio of 2:1. The ether and ethyl acetate mixed eluent were washed and flash column chromatography on silica gel to give the product 3aa.
85% With ammonium peroxodisulphate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation; General procedure for the prepration of 3- alkylquinoxalin-2(1H)-ones General procedure: To a solution of quinoxalin-2(1H)-ones 1 (0.3 mmol) and aliphatic acid 2 (0.75 mmol) in DMSO (3 mL) was added (NH4)2S2O8 (0.9 mmol). The reaction mixture was stirred at room temperature under the irradiation of 10 W blue LED lamps (440-445 nm) under N2 atmosphere conditions. The progress of the reaction was monitored by TLC. The reaction typically took within 24 hours. After completion, water (10mL) was added and the mixture was extracted with EtOAc (10 mL× 3), the solvent was then removed under vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired products 3.
85% With cerium(III) trichloride; potassium-t-butoxide In acetonitrile for 24h; Sealed tube; Irradiation;
60% With cerium(III) trichloride; 1,1,1-trichloroethanol; tetra-n-butyl-ammonium chloride In acetonitrile at 20℃; for 12h; Irradiation;
60% With cerium(III) trichloride; 1,1,1-trichloroethanol; [bis(acetoxy)iodo]benzene; tetra-n-butyl-ammonium chloride In acetonitrile at 20℃; for 12h; Irradiation;
57% With tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate In dimethyl sulfoxide at 20℃; for 12h; Schlenk technique; Irradiation; regioselective reaction;

  • 39
  • [ 6479-18-1 ]
  • [ 1872262-63-9 ]
  • [ 2374203-39-9 ]
YieldReaction ConditionsOperation in experiment
62% With 1,4-diaza-bicyclo[2.2.2]octane; tris(bipyridine)ruthenium(II) dichloride hexahydrate In N,N-dimethyl acetamide at 20℃; for 2h; Schlenk technique; Sealed tube; Irradiation; regioselective reaction;
  • 40
  • [ 6479-18-1 ]
  • 2-[(cyclohexylcarbonyl)oxy]-1H-isoindole-1,3(2H)-dione [ No CAS ]
  • 3-cyclohexyl-1-methylquinoxaline-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With Eosin Y; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 40h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;
99% With Eosin Y; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 40h; Inert atmosphere; Irradiation; Schlenk technique; 16 Example 16 In a 10 mL Schlenk tube, add N-methylquinoxalinone (1.0 mmol, 160 mg), N-cyclohexanoyloxyphthalimide (1.2 mmol, 327 mg), and trifluoroacetic acid (0.5 mmol, 57 mg), Na2-eosin Y (0.01 mmol, 7 mg), DMSO (3.0 mL), the reaction system was protected with N2, and reacted at room temperature under 3W white light for 40 h. After the reaction was completed, the reaction solution was washed with water, extracted with dichloromethane, and separated to obtain an aqueous layer and an organic layer. The organic layer was dried over anhydrous sodium sulfate, filtered to remove the residue, and the obtained filtrate was concentrated by distillation under reduced pressure and then subjected to column chromatography. Separation, using a mixed solvent of petroleum ether and ethyl acetate in a volume ratio of 15: 1 as the eluent, collecting the eluate containing the target compound, evaporating the solvent and drying to obtain the targetN-methyl-3-cyclohexylquinoxalinone(White solid) 240mg, yield 99%, i
92% With tetrabutylammonium tetrafluoroborate In N,N-dimethyl acetamide at 20℃; for 12h; Electrolysis;
91% With triethylamine at 20℃; for 24h; Inert atmosphere; Irradiation;
74% With 1,4-diaza-bicyclo[2.2.2]octane; tris(bipyridine)ruthenium(II) dichloride hexahydrate In N,N-dimethyl acetamide at 25℃; Schlenk technique; Sealed tube; Irradiation; regioselective reaction;
66% With nickel(II) chloride hexahydrate; lithium perchlorate; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide at 60℃; for 3h; Sealed tube; Inert atmosphere; Electrochemical reaction;
66% With nickel(II) chloride hexahydrate; lithium perchlorate; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide at 60℃; for 3.5h; Sealed tube; Inert atmosphere; Electrochemical reaction; 17 Example 17: Synthesis of 3-cyclohexyl-1-methylquinoxaline-2(1H)-one by electrochemical method In a 10ml single-chamber electrolytic cell, add the raw materials 1-methylquinoxaline-2(1H)-one (0.3mmol), redox active ester (0.6mmol), LiClO4 (1.0mmol), NiCl2.6H2O(0.6 mmol), 4,4'-di-tert-butyl-2,2'-bipyridine (0.6 mmol). Seal the device and inject argon into the tube (three times). Then, under an argon atmosphere, N,N-dimethylacetamide (DMA, 4.0 mL) and triethylamine (0.25 mL) were added via a syringe and stoppered with a rubber stopper, and an argon-filled balloon was inserted into the bottle. The mixture was first reacted under magnetic stirring at 60°C for 30 minutes, and then electrolyzed at a current density of 8 mA/cm2 for 3 hours. After the reaction was completed, the mixture was quenched with water and extracted with ethyl acetate (3×10 ml). The organic phase is concentrated on a rotary evaporator. Purify the desired product by column chromatography in a silica gel (petroleum ether: ethyl acetate) system and separate it by column chromatography to obtain 3-cyclohexyl-1-methylquinoxalin-2(1H)-one. Yield: 66%.

  • 41
  • [ 6479-18-1 ]
  • [ 1872262-74-2 ]
  • [ 2374203-38-8 ]
YieldReaction ConditionsOperation in experiment
81% With tetrabutylammonium tetrafluoroborate In N,N-dimethyl acetamide at 20℃; for 12h; Electrolysis;
67% With 1,4-diaza-bicyclo[2.2.2]octane; tris(bipyridine)ruthenium(II) dichloride hexahydrate In N,N-dimethyl acetamide at 20℃; for 2h; Schlenk technique; Sealed tube; Irradiation; regioselective reaction;
  • 42
  • [ 6479-18-1 ]
  • [ 1538551-54-0 ]
  • [ 13297-40-0 ]
YieldReaction ConditionsOperation in experiment
71% With Eosin Y; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 40h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;
  • 43
  • [ 6479-18-1 ]
  • 1,3-dioxoisoindolin-2-yl pent-4-enoate [ No CAS ]
  • 3-(but-3-en-1-yl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With Eosin Y; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 40h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;
87% With Eosin Y; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 40h; Inert atmosphere; Irradiation; Schlenk technique; 14 Example 14 Add N-methylquinoxalinone (1.0mmol, 160mg) to a 10mL Schlenk tube,N- (1-butyryloxy) phthalimide(1.2 mmol, 277 mg), trifluoroacetic acid (0.5 mmol, 57 mg), Na2-eosin Y (0.01 mmol, 7 mg), DMSO (3.0 mL), the reaction system was protected with N2, and reacted at room temperature under 3W white light for 40 h. After the reaction is completed, the reaction solution is washed with water, extracted with dichloromethane, and separated to obtain an aqueous layer and an organic layer. The organic layer is dried over anhydrous sodium sulfate, filtered to remove the residue, and the obtained filtrate is concentrated by distillation under reduced pressure and then subjected to column chromatography Separation, using a mixed solvent of petroleum ether and ethyl acetate in a volume ratio of 15: 1 as the eluent, collecting the eluate containing the target compound, evaporating the solvent and drying to obtain the target productN-methyl-3-(1-allyl)Quinoxalinone(Yellow solid) 186mg, yield 87%,
30% With tris[2-phenylpyridinato-C2,N]iridium(III); trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; regioselective reaction;
  • 44
  • [ 6479-18-1 ]
  • 1,3-dioxoisoindolin-2-yl isobutyrate [ No CAS ]
  • 3-(iso-propyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With Eosin Y; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 40h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;
96% With Eosin Y; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 40h; Inert atmosphere; Irradiation; Schlenk technique; 15 Example 15 In a 10 mL Schlenk tube, add N-methylquinoxalinone (1.0 mmol, 160 mg), N-isopropyloxyphthalimide (1.2 mmol, 279 mg), and trifluoroacetic acid (0.5 mmol, 57 mg), Na2-eosin Y (0.01 mmol, 7 mg), DMSO (3.0 mL), the reaction system was protected with N2, and reacted at room temperature under 3W white light for 40 h. After the reaction is completed, the reaction solution is washed with water, extracted with dichloromethane, and separated to obtain an aqueous layer and an organic layer. The organic layer is dried over anhydrous sodium sulfate, filtered to remove the residue, and the obtained filtrate is concentrated by distillation under reduced pressure and then subjected to column chromatography Separation, using a mixed solvent of petroleum ether and ethyl acetate in a volume ratio of 15: 1 as the eluent, collecting the eluate containing the target compound, evaporating the solvent and drying to obtain the target product N-methyl-3-isopropyl Quinoxalinone (white solid) 194mg, yield 96%,
76% With tetrabutylammonium tetrafluoroborate In N,N-dimethyl acetamide at 20℃; for 12h; Electrolysis;
60% With tris[2-phenylpyridinato-C2,N]iridium(III); trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; regioselective reaction;

  • 45
  • [ 1196-57-2 ]
  • [ 6479-18-1 ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate In N,N-dimethyl-formamide at 20℃;
70% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;
With potassium carbonate In dimethyl sulfoxide at 20℃;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; 2.2 The preparation of quinoxalin-2(1H)-ones[1] General procedure: To a suspension of o-arylenediamine (1 equiv.) in ethanol was added ethyl glyoxalate (1.1equiv.). The mixture was stirred at reflux for 1 h, then at room temperature overnight. Theprecipitated solid was filtered and washed with ethanol, then dried to give quinoxalinone. To asuspension of quinoxalinone (1 equiv.) in DMF was added potassium carbonate (1.2 equiv.) andthe corresponding halogenoalcane (1.6 equiv.). The mixture was stirred at room temperatureovernight. Ethyl acetate and water were added. The aqueous layer was extracted twice withEtOAc. The combined organic layers were washed with a saturated solution of NaCl, dried overMgSO4, filtered, and evaporated under reduced pressure. The residue is purified by flashchromatography over silica gel to afford the desired product N-alkyl quinoxalinone (Scheme S1).

  • 46
  • [ 20934-50-3 ]
  • [ 6479-18-1 ]
YieldReaction ConditionsOperation in experiment
With camphor-10-sulfonic acid In toluene for 17h; Reflux; 1-Methylquinoxalin-2(1H)-one 3 To a solution of amine 1 (100 mg, 0.617 mmol) in dry PhMe (2.5 mL) was added CSA (14 mg, 0.06 mmol). The mixture was heated under reflux for 17 h under air. After cooling to rt, the mixture was diluted with EtOAc (150 mL) and water (50 mL). The organic layer was separated, washed with brine (50 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. Purification by column chromatography on silica gel, eluting with petrol-EtOAc (1:1) gave a mixture (ratio 1:1.2) of amine 1 and imine 3 as a solid (24 mg, 24%); data for 3: 1H NMR (400 MHz, DMSO-d6) δ = 8.24 (1H, s, CH), 7.82 (1H, dd, J = 8.0, 1.5 Hz, CH), 7.71-7.63 (1H, m, CH), 7.62-7.55 (1H, m, CH), 7.44-7.35 (1H, m, CH), 3.60 (3H, s, CH3); 13C NMR (100 MHz, DMSO-d6) δ = 154.8, 150.6, 133.6, 133.1, 131.5, 130.0, 123.9, 115.4, 29.0.
  • 47
  • [ 6479-18-1 ]
  • [ 100-49-2 ]
  • 3-(cyclohexylmethoxy)-1-methylquinoxalin-2(1H)-one [ No CAS ]
  • 48
  • [ 6479-18-1 ]
  • [ 53293-00-8 ]
  • 1-methyl-3-(propan-4-yne-1-yl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tris(bipyridine)ruthenium(II) dichloride hexahydrate; [bis(acetoxy)iodo]benzene In chloroform at 25℃; for 6h; Microwave irradiation; Photolysis; 5 The specific reaction conditions are as follows Iodine diacetate (10 mmol), 6-heptynoic acid (20 mmol) was added to a round bottom flask, dissolved in 25 ml of chloroform, and concentrated to dryness under reduced pressure at 50 ° C to give bis(6-heptynoic acid) as an oil. Iodobenzene 2f, used without purification, was used directly in the next reaction.1-Methylquinoxaline-2(1Η)-one la (0.2 mmol), bis(6-heptynoic acid)iodobenzene 2f (0.44 mmol) was added in a 10 mL reaction tube at 25 ° C, Ru (bpy) 3C12 · 6H20 (0·002 mmol), PEG-200 (1 mL), mixed uniformly, and then stirred under a 3w blue LED lamp for 6 h. After the completion of the reaction by TLC, the mixture was extracted with cyclopentyl methyl ether (2 ml of X3), and the upper extract was taken and concentrated in vacuo at 50 ° C until solvent was obtained to obtain crude product, and then oil was used in a volume ratio of 2:1.The ether and ethyl acetate mixed eluent were washed, and the column was flash column chromatography to obtain 1-methyl-3(propyl-4-yn-1-yl)quinoxaline-2 (1H)- The ketone product 4af was 38.9 mg as a white solid, yield 86%.
  • 49
  • [ 6479-18-1 ]
  • [ 828-51-3 ]
  • [ 1029963-99-2 ]
YieldReaction ConditionsOperation in experiment
86% With ammonium peroxodisulphate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation; General procedure for the prepration of 3- alkylquinoxalin-2(1H)-ones General procedure: To a solution of quinoxalin-2(1H)-ones 1 (0.3 mmol) and aliphatic acid 2 (0.75 mmol) in DMSO (3 mL) was added (NH4)2S2O8 (0.9 mmol). The reaction mixture was stirred at room temperature under the irradiation of 10 W blue LED lamps (440-445 nm) under N2 atmosphere conditions. The progress of the reaction was monitored by TLC. The reaction typically took within 24 hours. After completion, water (10mL) was added and the mixture was extracted with EtOAc (10 mL× 3), the solvent was then removed under vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired products 3.
83% With tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate; [bis(acetoxy)iodo]benzene In chloroform at 25℃; for 6h; Microwave irradiation; Photolysis; 6 The specific reaction conditions are as follows To the round-bottomed flask, iodobenzene diacetate (10 mmol), ruthenium formic acid (20 mmol), and dissolved in 25 ml of chloroform, and concentrated to dryness under reduced pressure at 50 ° C to give 2 g of diamantanecarboxylic acid iodobenzene. It was used directly in the next reaction without purification.1-Methylquinoxaline-2(1Η)-one la (0.2 mmol), diamantanecarboxylic acid iodobenzene 2 g (0.44 mmol), Ru(bpy), were sequentially added to a 10 mL reaction tube at 25 °C. 3CI2 * 6Η2Ο (0.002mmol), PEG-200 (lmL), mixed evenly, and then stirred under a 3w blue LED lamp for 8h. After completion of the reaction by TLC, the mixture was extracted with cyclopentyl methyl ether (2 ml of X 3 ), and the extract was taken and concentrated in vacuo at 50 ° C until solvent was obtained to obtain crude product, and then oil was used in a volume ratio of 2:1. The ether and ethyl acetate mixed eluent was washed and flash column chromatography on silica gel to obtain 1-methyl-3-adamantylquinoxaline-2 (1H)-one product 4ag in the present example as a white solid 48.8 Mg, yield 83%.
76% With cerium(III) trichloride; potassium-t-butoxide In acetonitrile for 24h; Sealed tube; Irradiation;
54% With cerium(III) trichloride; 1,1,1-trichloroethanol; tetra-n-butyl-ammonium chloride In acetonitrile at 20℃; for 12h; Irradiation;
54% With cerium(III) trichloride; 1,1,1-trichloroethanol; [bis(acetoxy)iodo]benzene; tetra-n-butyl-ammonium chloride In acetonitrile at 20℃; for 12h; Irradiation;

  • 50
  • [ 6479-18-1 ]
  • [ 25812-30-0 ]
  • C23H28N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tris(bipyridine)ruthenium(II) dichloride hexahydrate; [bis(acetoxy)iodo]benzene; In chloroform; at 25℃; for 6h;Microwave irradiation; Photolysis; odine diacetate (10 mmol), propionic acid (20 mmol) was added to a round bottom flask, dissolved in 25 ml of chloroform, and concentrated to dryness under reduced pressure at 50 C to obtain iodobenzene 2b dipropionate, which was used without purification. In the next step.In a 10 mL reaction tube, 1-methylquinoxaline-2(1Eta)-one la (0.2 mmol), dijigfibrozol iodobenzene 2i (0.44 mmol), Ru (in order) at 25 C Bpy) 3CI2 * 6Eta2Omicron (0.002mmol), PEG-200 (lmL), mixed evenly, and then stirred under a 3w blue LED lamp for 8h. After completion of the reaction by TLC, the mixture was extracted with cyclopentyl methyl ether (2 ml of X 3 ), and the extract was taken and concentrated in vacuo at 50 C until solvent was obtained to obtain crude product, and then oil was used in a volume ratio of 2:1. etherRinse with ethyl acetate mixed with eluent, and flash column chromatography on silica gel to obtain 1-methyl-3-gyfizilidine in this example.The porphyrin-2 (1H)-one product 4ai was 47.3 mg as a white solid, yield 65%.
  • 51
  • [ 6479-18-1 ]
  • [ 2923-56-0 ]
  • 1-methyl-3-(4-(trifluoromethyl)phenyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With C114H108N24O24; potassium carbonate; In dimethyl sulfoxide; for 24h;Irradiation; in room temperature,N-methylquinoxaline-2 (1H) -one (0.1 mmol), 4-trifluoromethylphenylhydrazine hydrochloride (0.3 mmol), 2D-COF-1 ( 4 mg), K2CO3 (0.3 mmol) and dimethyl sulfoxide (1.5 mL). Stir in the air for 24 hours under the irradiation of a blue LED lamp with a power of 34W and a wavelength of 400-500nm. The reaction was stopped, extracted with ethyl acetate and water, and then concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding quinoxalinone derivative was obtained by flash column chromatography (silica gel column) (light yellow solid 21 mg, yield 69%).
  • 52
  • [ 6479-18-1 ]
  • [ 40566-85-6 ]
  • C18H16N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With C114H108N24O24; potassium carbonate; In dimethyl sulfoxide; for 24h;Irradiation; At room temperature, N-methylquinoxaline-2 (1H) -one (0.1 mmol), <strong>[40566-85-6]4-ethoxycarbonylphenylhydrazine hydrochloride</strong> (0.3 mmol), 2D-COF -1 (4 mg), K2CO3 (0.3 mmol) and dimethyl sulfoxide (1.5 mL). Stir for 24 hours under the irradiation of a blue LED with a power of 34W and a wavelength of 400-500nm. The reaction was stopped in air, extracted with ethyl acetate and water, and then concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding quinoxalinone derivative was obtained by flash column chromatography (silica gel column) (light yellow solid 25 mg, yield 75%).
  • 53
  • [ 6479-18-1 ]
  • [ 637-04-7 ]
  • 1-methyl-3-(m-tolyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With C114H108N24O24; potassium carbonate; In dimethyl sulfoxide; for 24h;Irradiation; in room temperature,N-methylquinoxaline-2 (1H) -one (0.1mmol), <strong>[637-04-7]3-methylphenylhydrazine hydrochloride</strong> (0.3mmol), 2D-COF-1 (4mg) K2CO3 (0.3 mmol) and dimethyl sulfoxide (1.5 mL). Stir in the air for 24 hours under the irradiation of a blue LED lamp with a power of 34W and a wavelength of 400-500nm. The reaction was stopped, extracted with ethyl acetate and water, and then concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding quinoxalinone derivative was obtained by flash column chromatography (silica gel column) (yellow solid 20 mg, yield 80%).
  • 54
  • [ 6479-18-1 ]
  • [ 2924-16-5 ]
  • [ 1057224-08-4 ]
YieldReaction ConditionsOperation in experiment
75% With C114H108N24O24; potassium carbonate; In dimethyl sulfoxide; for 24h;Irradiation; in room temperature,N-methylquinoxaline-2 (1H) -one (0.1 mmol) was sequentially added to a 5 mL photoreaction tube.3-fluoromethylphenylhydrazine hydrochloride (0.3 mmol), 2D-COF-1 (4 mg), K2CO3 (0.3 mmol) and dimethyl sulfoxide (1.5 mL). Stir in the air for 24 hours under the irradiation of a blue LED lamp with a power of 34W and a wavelength of 400-500nm. The reaction was stopped, extracted with ethyl acetate and water, and then concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding quinoxalinone derivative was obtained by flash column chromatography (silica gel column) (light yellow solid 19 mg, yield 75%).
  • 55
  • [ 6479-18-1 ]
  • [ 635-26-7 ]
  • 1-methyl-3-(o-tolyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With C114H108N24O24; potassium carbonate; In dimethyl sulfoxide; for 24h;Irradiation; in room temperature,In a 5 mL photoreaction tube, N-methylquinoxaline-2 (1H) -one (0.1 mmol), <strong>[635-26-7]2-methylphenylhydrazine hydrochloride</strong> (0.3 mmol), and 2D-COF-1 (4 mg) were sequentially added. K2CO3 (0.3 mmol) and dimethyl sulfoxide (1.5 mL). Stir in the air for 24 hours under the irradiation of a blue LED lamp with a power of 34W and a wavelength of 400-500nm. The reaction was stopped, extracted with ethyl acetate and water, and then concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) was obtained to obtain the corresponding quinoxalinone derivative (light yellow solid 18 mg, yield 72%).
  • 56
  • [ 6479-18-1 ]
  • [ 16726-41-3 ]
  • [ 107290-48-2 ]
YieldReaction ConditionsOperation in experiment
84% With C114H108N24O24; potassium carbonate In dimethyl sulfoxide for 18h; Irradiation; 27 Example 27 in room temperature,N-methylquinoxaline-2 (1H) -one (0.1 mmol) was sequentially added to a 5 mL photoreaction tube.Isopropylhydrazine hydrochloride (0.2 mmol), 2D-COF-1 (4 mg),K2CO3 (0.2 mmol) and dimethyl sulfoxide (1.5 mL). Under air, at a power of 34W,Stir under a blue LED with a wavelength of 400-500nm for 18 hours. The reaction was stopped, extracted with ethyl acetate and water, and then concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding quinoxalinone derivative was obtained by flash column chromatography (silica gel column) (light yellow solid 17 mg, yield 84%).
  • 57
  • [ 6479-18-1 ]
  • [ 24214-72-0 ]
  • 3-cyclopentyl-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With C114H108N24O24; potassium carbonate; In dimethyl sulfoxide; for 18h;Irradiation; in room temperature,In a 5 mL photoreaction tube, N-methylquinoxaline-2 (1H) -one (0.1 mmol), <strong>[24214-72-0]cyclopentylhydrazine hydrochloride</strong> (0.2 mmol), 2D-COF-1 (4 mg), and K2CO3 were sequentially added. (0.2 mmol) and dimethyl sulfoxide (1.5 mL). Stir in the air for 18 hours under the irradiation of a blue LED lamp with a power of 34W and a wavelength of 400-500nm. The reaction was stopped, extracted with ethyl acetate and water, and then concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding quinoxalinone derivative was obtained by flash column chromatography (silica gel column) (light yellow solid 17mg, yield 76%)
  • 58
  • [ 100-42-5 ]
  • [ 536-57-2 ]
  • [ 6479-18-1 ]
  • 1-methyl-3-(1-phenyl-2-tosylethyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tert.-butylhydroperoxide In water; 1,2-dichloro-ethane at 45℃; for 24h; Inert atmosphere;
58% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,2-dichloro-ethane at 20℃; for 6h; Irradiation; 3. General procedure for visible-light-induced multi-component reaction of quinoxalin-2(1H)-ones, alkenes and sulfinic acids. General procedure: To a solution of quinoxalin-2(H)-one 1 (0.1 mmol), arylsulfinic acid 3 (0.2 mmol), 4CzIPN (0.001 mmol, 2 mol %), DCE ( 2 mL) was added alkene 2 (0.2 mmol). The reaction mixture was open to the air and stirred under the irradiation of 3 W blue LEDs at room temperature for 6 h. After completion of the reaction, the solution was concentrated in vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired product 4 or 5.
  • 59
  • [ 292638-84-7 ]
  • [ 6479-18-1 ]
  • [ 1195-33-1 ]
  • 3-(2-((4-bromophenyl)sulfonyl)-1-phenylethyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
  • 60
  • [ 6479-18-1 ]
  • [ 5813-86-5 ]
  • 3-methoxy-N-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)benzamide [ No CAS ]
  • 61
  • [ 6479-18-1 ]
  • [ 938-73-8 ]
  • 2-ethoxy-N-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)benzamide [ No CAS ]
  • 62
  • [ 6479-18-1 ]
  • [ 1891-90-3 ]
  • N-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)-4-(trifluoromethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With Selectfluor In acetonitrile at 60℃; for 4h; Green chemistry;
  • 63
  • [ 6479-18-1 ]
  • [ 541-35-5 ]
  • C13H15N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With Selectfluor In acetonitrile at 60℃; for 4h; Green chemistry;
  • 64
  • [ 6479-18-1 ]
  • [ 1872262-64-0 ]
  • [ 1057222-09-9 ]
YieldReaction ConditionsOperation in experiment
81% With triethylamine at 20℃; for 24h; Inert atmosphere; Irradiation;
27% With tris[2-phenylpyridinato-C2,N]iridium(III); trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; regioselective reaction;
  • 65
  • [ 6479-18-1 ]
  • [ 84379-71-5 ]
  • 1-methyl-3-phenethylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With tris[2-phenylpyridinato-C2,N]iridium(III); trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; regioselective reaction;
  • 66
  • [ 6479-18-1 ]
  • [ 2079-95-0 ]
  • 1-methyl-3-(tetradecylthio)quinoxaline-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.2% With trifluoroacetic acid In acetonitrile at 30℃; for 10h; Electrolysis; 6 Example 6 1-methyl-3-(tetradecylthio)quinoxaline-2(1H)-one (III-f) Add compound (I) 1-methylquinoxalin-2-one (64 mg, 0.4 mmol) and tetradecyl mercaptan (1382.4 mg, 6.0 mmol) into a 50 mL open round bottom flask equipped with magnetic stirring. Trifluoroacetic acid (91mg), acetonitrile (10mL) was added to the mixture, and the reaction was stirred at 30°C for 10 hours under 10mA current electrolysis. TLC tracked to the end of the reaction (using petroleum ether and ethyl acetate in a volume ratio of 5:1). Ester mixed solvent is used as a developing agent), and the reaction mixture is washed with saturated brine. The mixture was extracted with ethyl acetate, and the combined organic layer was dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to obtain 116.7 mg of the product with a yield of 75.2% and an HPLC purity of 96.7%.
55% With oxygen; rhodamine 6G; trifluoroacetic acid at 20℃; for 24h; Schlenk technique; Irradiation; regioselective reaction;
52.3% With rhodamine 6G; trifluoroacetic acid at 30℃; for 10h; Irradiation; 6 Example 6 1-Methyl-3- (tetradecylthio) quinoxaline-2 (1H) -one (I-f) In a 50 mL open round bottom flask equipped with a magnetic stir bar, add compound (II) 1-methylquinoxaline-2-one (64 mg, 0.4 mmol), rhodamine 6G (19.2 mg, 0.04 mmol)Tetradecyl mercaptan (1382.4 mg, 6 mmol), trifluoroacetic acid (91 mg), and the mixture was irradiated with 3W blue light,The reaction was stirred at 30 ° C for 10 hours. The reaction mixture was quenched with a saturated aqueous NaHCO3 solution and washed with water.The mixture was extracted with ethyl acetate, and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure.The crude product was purified on a silica gel column using n-hexane / ethyl acetate to obtain 81.2 mg of the product with a yield of 52.3% and a HPLC purity of 96.7%.
  • 67
  • [ 6479-18-1 ]
  • [ 4410-99-5 ]
  • 1-methyl-3-(2-phenethylthio)quinoxaline-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With oxygen; rhodamine 6G; trifluoroacetic acid at 20℃; for 24h; Schlenk technique; Irradiation; regioselective reaction;
79.6% With trifluorormethanesulfonic acid; rhodamine 6G at 40℃; for 24h; Irradiation; 7 Example 7 1-Methyl-3- (phenethylthio) quinoxaline-2 (1H) -one (I-g) In a 50 mL open round bottom flask equipped with a magnetic stir bar, add compound (II) 1-methylquinoxaline-2-one (64 mg, 0.4 mmol),Rhodamine 6G (9.6mg, 0.02mmol), phenethyl mercaptan (1105.8mg, 8mmol),Trifluoromethanesulfonic acid (180 mg, 1.2 mmol), and the mixture was irradiated with 3W blue light,The reaction was stirred at 40 ° C for 24 hours, and the reaction mixture was quenched with a saturated aqueous solution of 310 ml of NaHCO and washed with water.The mixture was extracted with ethyl acetate, and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure.The crude product was purified on a silica gel column using n-hexane / ethyl acetate to obtain 94.2 mg of the product with a yield of 79.6% and an HPLC purity of 98.8%.
79.6% With trifluorormethanesulfonic acid In acetonitrile at 40℃; for 18h; Electrolysis; 7 Example 7 1-Methyl-3-(phenethylthio)quinoxaline-2(1H)-one (III-g) Add compound (I) 1-methylquinoxalin-2-one (64 mg, 0.4 mmol) into a 50 mL open round bottom flask equipped with magnetic stirring,Phenyl ethyl mercaptan (1105.8 mg, 8 mmol), trifluoromethanesulfonic acid (180 mg, 1.2 mmol), acetonitrile (10 mL) was added to the mixture, and the reaction was stirred at 40°C for 18 hours under 10 mA current electrolysis. TLC traced to After the reaction was completed (using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 5:1 as a developing agent), the reaction mixture was washed with saturated brine. The mixture was extracted with ethyl acetate, and the combined organic layer was dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to obtain 94.2 mg of the product with a yield of 79.6% and an HPLC purity of 98.8%.
  • 68
  • [ 6479-18-1 ]
  • [ 623-51-8 ]
  • 2-((4-methyl-3-oxo-3,4-dihydroquinoxaline-2-yl)thio)acetic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With oxygen; rhodamine 6G; trifluoroacetic acid at 20℃; for 24h; Schlenk technique; Irradiation; regioselective reaction;
75.4% With sulfuric acid; eosin y In N,N-dimethyl-formamide at 35℃; for 20h; Irradiation; 8 Example 8 2-((4-methyl-3-oxo-3,4-dihydroquinoxaline-2-yl) thio) ethyl acetate (I-h) In a 50 mL open round bottom flask equipped with a magnetic stir bar, add compound (II) 1-methylquinoxaline-2-one (64 mg, 0.4 mmol),Eosin Y (25.8mg, 0.04mmol), ethyl mercaptoacetate (721.0mg, 8mmol),Sulfuric acid (117.6mg, 1.2mmol), DMF (5ml) was added to the mixture, and 3W blue light was irradiated,The reaction was stirred at 35 ° C for 20 hours. The reaction mixture was quenched with saturated aqueous NaHCO3 solution and washed with water.The mixture was extracted with ethyl acetate, and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure.The crude product was purified on a silica gel column using n-hexane / ethyl acetate to obtain 83.8 mg of the product with a yield of 75.4% and a purity of 97.2% by HPLC.
75.4% With sulfuric acid In N,N-dimethyl-formamide at 35℃; for 20h; Electrolysis; 8 Example 8 2-((4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)thio)ethyl acetate (III-h) In a 50 mL open round bottom flask equipped with magnetic stirring was added compound (I) 1-methylquinoxalin-2-one (64 mg, 0.4 mmol), ethyl mercaptoacetate (721.0 mg, 8 mmol), sulfuric acid (117.6 mg, 1.2mmol), DMF (10mL) was added to the mixture, and the reaction was stirred at 35°C for 20 hours under electrolysis with a current of 10mA. TLC tracked until the end of the reaction (using petroleum ether and ethyl acetate in a volume ratio of 5:1 The mixed solvent is used as a developing agent), and the reaction mixture is washed with saturated brine. The mixture was extracted with ethyl acetate, and the combined organic layer was dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to obtain 83.8 mg of the product with a yield of 75.4% and an HPLC purity of 97.2%.
  • 69
  • [ 109-80-8 ]
  • [ 6479-18-1 ]
  • 3-((3-mercaptopropyl)thio)-1-methylquinoxaline-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.5% With acetic acid In toluene at 25℃; for 18h; Electrolysis; 9 Example 9 3-((3-Mercaptopropyl)thio)-1-methylquinolin-2(1H)-one (III-i) Add compound (I) 1-methylquinoxalin-2-one (64 mg, 0.4 mmol) into a 50 mL open round bottom flask equipped with magnetic stirring,propane dithiol (216.4mg, 2mmol), acetic acid (72mg, 1.2mmol), the mixture was dissolved in toluene (8mL), under 10mA current electrolysis, the reaction was stirred at 25°C for 18 hours, TLC tracked until the end of the reaction ( Using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 5:1 as a developing agent), the reaction mixture was washed with saturated brine. The mixture was extracted with ethyl acetate, and the combined organic layer was dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to obtain 81.39 mg of the product with a yield of 76.5% and an HPLC purity of 96.5%.
41% With oxygen; rhodamine 6G; trifluoroacetic acid at 20℃; for 24h; Schlenk technique; Irradiation; regioselective reaction;
37.2% With rhodamine 6G; acetic acid In toluene at 25℃; for 18h; Irradiation; 9 Example 9 3-((3-mercaptopropyl) thio) -1-methylquinoline-2 (1H) -one (I-i) In a 50 mL open round bottom flask equipped with a magnetic stir bar, add compound (II) 1-methylquinoxaline-2-one (64 mg, 0.4 mmol),Rhodamine 6G (38.4mg, 0.08mmol), propanedithiol (216.4mg, 2mmol),Acetic acid (72mg, 1.2mmol), the mixture was dissolved in toluene (5ml),Irradiate with 3W blue light, stir the reaction at 25 ° C for 18 hours, quench the reaction mixture with saturated aqueous NaHCO3 solution, and wash with water.The mixture was extracted with ethyl acetate, and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure.The crude product was purified on a silica gel column using n-hexane / ethyl acetate to obtain 39.5 mg of the product with a yield of 37.2% and a HPLC purity of 96.5%.
  • 70
  • [ 6479-18-1 ]
  • [ 870-23-5 ]
  • 3-(allylthio)-1-methylquinoxaline-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.1% With trifluoroacetic acid In toluene at 25℃; for 15h; Electrolysis; 10 Example 10 3-(allylthio)-1-methylquinoline-2(1H)-one (III-j) Add compound (I) 1-methylquinoxalin-2-one (69 mg, 0.4 mmol), allyl mercaptan (294.6 mg, 4 mmol), and trifluoroacetic acid into a 50 mL open round bottom flask equipped with magnetic stirring. (91mg, 0.8mmol), toluene (8mL) was added to the mixture, under 10mA current electrolysis, the reaction was stirred at 25°C for 15 hours, TLC tracked to the end of the reaction (with a volume ratio of 5:1 petroleum ether and ethyl acetate Ester mixed solvent is used as a developing agent), and the reaction mixture is washed with saturated brine. The mixture was extracted with ethyl acetate, and the combined organic layer was dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to obtain 77.2 mg of the product with a yield of 83.1% and an HPLC purity of 98.2%.
45% With oxygen; rhodamine 6G; trifluoroacetic acid at 20℃; for 24h; Schlenk technique; Irradiation; regioselective reaction;
44.7% With methylene blue; trifluoroacetic acid In toluene at 25℃; for 24h; Irradiation; 10 Example 10 3- (allylthio) -1-methylquinoline-2 (1H) -one (I-j) In a 50 mL open round bottom flask equipped with a magnetic stir bar, add compound (II) 1-methylquinoxaline-2-one (69 mg, 0.4 mmol),Methylene blue (9.6 mg, 0.04 mmol), allyl mercaptan (294.6 mg, 4 mmol), trifluoroacetic acid (91 mg, 0.8 mmol),Toluene (5ml) was added to the mixture and irradiated with 3W blue light.The reaction was stirred at 25 ° C for 24 hours. The reaction mixture was quenched with a saturated aqueous NaHCO3 solution and washed with water.The mixture was extracted with ethyl acetate, and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure.The crude product was purified on a silica gel column using n-hexane / ethyl acetate to obtain 41.5 mg of the product with a yield of 44.7% and an HPLC purity of 98.2%.
  • 71
  • [ 592-41-6 ]
  • [ 6479-18-1 ]
  • 3-(1-azidohexan-2-yl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With trimethylsilylazide; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane; 1,2-dichloro-ethane at 23℃; for 0.0166667h;
84% With [bis(acetoxy)iodo]benzene; trimethylsilylazide In acetonitrile at -10℃; for 12h; Schlenk technique; Inert atmosphere; Intermolecular Azidoheteroarylation of Alkenes; General Procedure General procedure: A Schlenk-tube equipped with a magnetic stir bar was charged with aquinoxalin2(1H)-one 2 (0.2 mmol), TMSN 3 (0.4 mmol, 2 equiv),PhI(OAc)2 (0.4 mmol, 2.0 equiv), and then evacuated and backfilledwith N2 for three times. Afterwards, an alkene 1 (0.4 mmol, 2.0 equiv)and CH3CN (1 mL) were added under N2 atmosphere. The reactionmixture in the closed Schlenk tube was stirred at -10 °C. After 12 h,the resulting mixture was extracted with CH2Cl2 (3 x 15 mL) and thecombined organic layers were dried (anhyd Na2SO4). After removal ofthe solvent under reduced pressure, the crude product was purifiedby column chromatography (eluent: PE:EA = 2:1) on silica gel to givethe product.
  • 72
  • [ 6479-18-1 ]
  • [ 2695-47-8 ]
  • 3-(1-azido-6-bromohexan-2-yl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With [bis(acetoxy)iodo]benzene; trimethylsilylazide In acetonitrile at -10℃; for 12h; Schlenk technique; Inert atmosphere; Intermolecular Azidoheteroarylation of Alkenes; General Procedure General procedure: A Schlenk-tube equipped with a magnetic stir bar was charged with aquinoxalin2(1H)-one 2 (0.2 mmol), TMSN 3 (0.4 mmol, 2 equiv),PhI(OAc)2 (0.4 mmol, 2.0 equiv), and then evacuated and backfilledwith N2 for three times. Afterwards, an alkene 1 (0.4 mmol, 2.0 equiv)and CH3CN (1 mL) were added under N2 atmosphere. The reactionmixture in the closed Schlenk tube was stirred at -10 °C. After 12 h,the resulting mixture was extracted with CH2Cl2 (3 x 15 mL) and thecombined organic layers were dried (anhyd Na2SO4). After removal ofthe solvent under reduced pressure, the crude product was purifiedby column chromatography (eluent: PE:EA = 2:1) on silica gel to givethe product.
83% With trimethylsilylazide; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane; 1,2-dichloro-ethane at 23℃; for 0.0166667h;
79% With trimethylsilylazide; 9-mesityl-10-methylacridin-10-ium perchlorate In dichloromethane at 20℃; for 0.5h; Irradiation;
  • 73
  • [ 6479-18-1 ]
  • [ 20934-51-4 ]
YieldReaction ConditionsOperation in experiment
96% With propane-1-thiol In acetonitrile for 12h; Irradiation; Green chemistry; General experimental procedure for the hydroxylation ofquinoxalin-2(1H)-ones General procedure: To a solution of quinoxalin-2(1H)-ones 1 (0.3mmol) and propane-1-thiol 2b (0.6 mmol) in CH3CN (1.5 mL) was addedg-C3N4 (10 mg). The reaction mixture was stirred under an ambient airatmosphere upon irradiation of 6 W blue LED lamps (445-450 nm) forabout 12h. After completion of the reaction, dichloromethane (10 mL)was added to the reaction mixture, g-C3N4 was filtered out of the mixture. Then, filtrate was concentrated in vacuo and the residue was purifiedthrough washing using a mixture solvent that consists of 10 mL ofpetroleum ether and 2 mL of ethyl acetate, followed by filtration anddrying to give solid product 3.
91% With ammonium peroxodisulphate; TPGS-750-M In lithium hydroxide monohydrate at 60℃; for 12h;
91% With ammonium peroxodisulphate In lithium hydroxide monohydrate at 60℃; for 12h; 1 The following Examples 1 to 11 all react according to the following reaction equation: The specific operation steps are: In a 10mL round bottom flask,N-substituted quinoxaline-2 (1H) -one derivative (1 mmol),Ammonium persulfate (2.5mmol),2wt% TPGS-750-M (aqueous solution) (2mL)The reaction was stirred with heating at 60 ° C.Thin-layer chromatography plates track the progress of the reaction, and the general reaction time is 12 hours. After the reaction was completed, the mixture was cooled to room temperature, the reaction mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate. The filtrate was concentrated on a rotary evaporator and dried under vacuum to obtain the pure 2,3-dihydroxyquinoxaline compound.
91% With tert.-butylnitrite; lithium hydroxide monohydrate In dimethyl sulfoxide at 100℃; for 3h; Sealed tube;
80% With ammonium peroxodisulphate In lithium hydroxide monohydrate; acetonitrile at 60℃; for 10h; General Procedure for the Synthesis of Oxidative Products General procedure: The mixture of quinoxalin-2(1H)-ones1-5 (0.2 mmol, 1.0 equiv.), (NH4)2S2O8 (0.6 mmol, 3.0 equiv.) was stirred in CH3CN/H2O (4: 1) (2.0 mL/mmol) in an oil bath at 60 oC, in a 20 mL tube under air. When the reaction was completed (detected by TLC), the mixture was cooled to room temperature. The reaction was quenched with H2O (10 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were dried over anhydrous Na2SO4 and then evaporated in vacuo to afford the corresponding oxidative products.
62% With toluene-4-sulfonic acid; 1-fluoro-4-methyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 72h;

  • 74
  • [ 6479-18-1 ]
  • [ 658-27-5 ]
  • [ 1057224-08-4 ]
  • 75
  • [ 6479-18-1 ]
  • [ 2251-76-5 ]
  • 3-(4-fluorobenzoyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With Acridine Red; In 1,2-dichloro-ethane; at 20℃; for 8h;Irradiation; At room temperature, add 1a (0.1mmol) and p-fluoroacetophenone acid 2d (0.2mmol) in a 15mL reaction tube in order.Photocatalyst acridine red (0.001 mmol), 1,2 dichloroethane 2mL, mix well,Then, under the irradiation of a 3w blue LED lamp, the reaction was stirred in the air for 8h.After the completion of the reaction was detected by TLC, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent.The crude product was obtained, and then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 5: 1.Flash column chromatography on a silica gel column yielded the 3ad product of this example as a 20.3 mg yellow solid with a yield of 72%.
  • 76
  • [ 6479-18-1 ]
  • [ 79478-02-7 ]
  • 1-methyl-3-(4-(trifluoromethyl)benzoyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With air In water; 1,2-dichloro-ethane at 20℃; Irradiation; Green chemistry; regioselective reaction;
71% With Acridine Red In 1,2-dichloro-ethane at 20℃; for 8h; Irradiation; 8 Example 8 At room temperature, add 1a (0.1 mmol) and p-trifluoromethylacetophenone acid for 2 h (0.2 mmol) in a 15 mL reaction tube in sequence.Photocatalyst acridine red (0.001 mmol), 1,2 dichloroethane 2mL, mix well,Then, under the irradiation of a 3w blue LED lamp, the reaction was stirred in the air for 8h. After the completion of the reaction was detected by TLC, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent.The crude product was obtained, and then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 5: 1.Flash column chromatography on a silica gel column gave the 3ah product of this example as a 23.6 mg yellow solid with a yield of 71%.
57% With 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane at 23℃; for 36h; Irradiation;
52% With [bis(acetoxy)iodo]benzene In water at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;

  • 77
  • [ 6479-18-1 ]
  • [ 815-17-8 ]
  • 1-methyl-3-pivaloylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With Acridine Red; In 1,2-dichloro-ethane; at 20℃; for 8h;Irradiation; At room temperature, 1a (0.1 mmol) was sequentially added to a 15 mL reaction tube.Tert-butyl ethanone acid 2k (0.2 mmol), photocatalyst acridine red (0.001 mmol), 1,2 dichloroethane 2 mL,Mix well, and then stir in the air for 8h under the irradiation of a 3w blue LED lamp. After the completion of the reaction was detected by TLC, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent.The crude product was obtained, and then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 5: 1.Flash column chromatography on a silica gel column to obtain the 3ak product of this example as 16.2 mg of a yellow solid with a yield of 72%
  • 78
  • [ 6479-18-1 ]
  • [ 5449-21-8 ]
  • 3-([1,1′-biphenyl]-4-carbonyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
  • 79
  • [ 6479-18-1 ]
  • [ 3112-46-7 ]
  • 1-methyl-3-(2,4,6-trimethylbenzoyl)quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With [bis(acetoxy)iodo]benzene In water at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;
  • 80
  • [ 6479-18-1 ]
  • [ 275818-95-6 ]
  • 3-(difluoromethyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
  • 81
  • [ 6479-18-1 ]
  • [ 7194-78-7 ]
  • 3-(3-bromobenzoyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
  • 82
  • [ 3698-28-0 ]
  • [ 6479-18-1 ]
  • [ 2926-29-6 ]
  • 3-(4,4,4-trifluoro-1-(2-methoxyphenyl)butan-2-yl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; Sealed tube;
70% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; 3 Example 3 At room temperature, quinoxalinone 1a (0.2 mmol), o-methoxyallylbenzene (0.4 mmol), sodium trifluoromethylsulfinate (0.4 mmol), potassium peroxodisulfate ( 0.6mmol), acetonitrile: water (4:1) 2.5mL, mixed evenly, then stirred at 80°C in the air for 24h. After detecting the completion of the reaction by TLC, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent to obtain a crude product, which was then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 10:1. Column flash column chromatography to obtain 4c of this example as a yellow solid 52.6mg, yield 70%.
66% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 12h; Irradiation; 28 Add the photocatalyst 2,4,5,6-tetra(9-carbazolyl)-isophthalonitrile (0.002 mmol), quinoxalinone 1a (0.2 mmol), and o-methoxyene into the 15mL reaction tube in sequence Propylbenzene 2j (0.4 mmol), sodium trifluoromethanesulfinate 3a (0.4 mmol), 4 mL of 1,4-dioxane/water (volume ratio 6:1), mix well, and then add 3W blue Under LED light irradiation, the reaction was carried out at room temperature in the air for 12 hours. After the completion of the reaction was detected by TLC, ethyl acetate was added to extract 3 times, the extract was concentrated under vacuum (0.08 Mpa) to solvent-free, and the crude product was obtained, and then petroleum ether and ethyl acetate with a volume ratio of 10:1 The mixed eluent was washed with silica gel column flash column chromatography to obtain 4j of this example as a yellow solid of 49.6 mg, with a yield of 66%.
66% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 12h; Irradiation; 3. General procedure for visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na General procedure: To a solution of quinoxalin-2(H)-one 1 (0.1 mmol), CF3SO2Na 3 (0.2 mmol), 4CziPN (0.001 mmol, 1 mol %), 1,4-dioxane/H 2 O (6/1, 2.5 mL) was added alkene 2 (0.2 mmol). The reaction mixture was open to the air and stirred under the irradiation of 3 W blue LEDs at room temperature for 12 h. After completion of the reaction, the solution was concentrated in vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired product 4.

  • 83
  • [ 6479-18-1 ]
  • [ 1736-60-3 ]
  • [ 2926-29-6 ]
  • 1-methyl-3-(4,4,4-trifluoro-1-(perfluorophenyl)butan-2-yl)-quinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; Sealed tube;
70% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; 5 Example 5 At room temperature, quinoxalinone 1a (0.2 mmol) was added to the 15 mL reaction tube in sequence. trimethoxyallyl pentafluorobenzene (0.4mmol), sodium trifluoromethanesulfinate (0.4mmol), potassium peroxodisulfate (0.6mmol), acetonitrile: water (4:1) 2.5mL, mix well, then The reaction was stirred at 80 °C in the air for 24h. After detecting the completion of the reaction by TLC, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent to obtain a crude product, which was then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 5:1. Column flash column chromatography to obtain 4e of this example as a yellow solid 61.0mg, yield 70%
57% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 12h; Irradiation; 29 Add the photocatalyst 2,4,5,6-tetrakis(9-carbazolyl)-isophthalonitrile (0.002 mmol), quinoxalinone 1a (0.2 mmol), and allyl pentafluoro in the 15mL reaction tube sequentially Benzene 2k (0.4 mmol), sodium trifluoromethanesulfinate 3a (0.4 mmol), 1,4-dioxane/water (volume ratio 6:1) 4 mL, mix well, and then add 3W blue LED Under the lamp irradiation, the reaction was carried out at room temperature in the air for 12 hours. After the reaction was detected by TLC, ethyl acetate was added and extracted three times. The extract was concentrated in a vacuum (0.08 Mpa) until there was no solvent to obtain the crude product. Then, the volume ratio of petroleum ether and ethyl acetate was 5:1. The mixed eluent was washed with silica gel column and flash column chromatography to obtain 4k of this example, which was 49.7 mg of white solid, and the yield was 57%.
57% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 12h; Irradiation; 3. General procedure for visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na General procedure: To a solution of quinoxalin-2(H)-one 1 (0.1 mmol), CF3SO2Na 3 (0.2 mmol), 4CziPN (0.001 mmol, 1 mol %), 1,4-dioxane/H 2 O (6/1, 2.5 mL) was added alkene 2 (0.2 mmol). The reaction mixture was open to the air and stirred under the irradiation of 3 W blue LEDs at room temperature for 12 h. After completion of the reaction, the solution was concentrated in vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired product 4.

  • 84
  • [ 6479-18-1 ]
  • [ 583-04-0 ]
  • [ 2926-29-6 ]
  • 4,4,4-trifluoro-2-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)butyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With [bis(acetoxy)iodo]benzene In ethyl acetate at 20℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction; 3.3. General experimental procedure General procedure: A Schlenk-tube equipped with a magnetic stir bar was charged with a quinoxalin2(1H)-one (0.2 mmol), CF3SO2Na (3 equiv, 0.6mmol), PhI(OAc)2 (3 equiv, 0.6mmol), and then evacuated and backfilled with N2 3 times. Afterwards, an alkene (2 equiv, 0.4 mmol), Ethyl Acetate (1mL) were added under N2 atmosphere. The tightly tube was string in room temperature. After 12 hours, the resulting mixture was extracted with Ethyl Acetate (3 x 15 mL) and the combined organic layers were dried over anhydrous Na2SO4. After removal of the solvent under reduced pressure, the crude product was purified by column chromatography on silica gel to give the product.
55% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; Sealed tube;
55% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; 6 Example 6 At room temperature, p-quinoxalinone 1a (0.2 mmol), allyl benzoate (0.4 mmol), sodium trifluoromethylsulfinate (0.4 mmol), potassium peroxodisulfate (0.6 mmol), acetonitrile: water (4:1) 2.5mL, mixed evenly, then stirred at 80°C in the air for 36h. After detection by TLC until the reaction was completed, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent to obtain a crude product, which was then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 10:1, silica gel Column flash column chromatography to obtain 4f of this example as a yellow solid 43.0mg, yield 55%.
  • 85
  • [ 6479-18-1 ]
  • [ 5428-09-1 ]
  • [ 2926-29-6 ]
  • 2-(4,4,4-trifluoro-2-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)butyl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; Sealed tube;
60% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; 7 Example 6 At room temperature, p-quinoxalinone 1a (0.2 mmol), allyl benzoate (0.4 mmol), sodium trifluoromethylsulfinate (0.4 mmol), potassium peroxodisulfate (0.6 mmol), acetonitrile: water (4:1) 2.5mL, mixed evenly, then stirred at 80°C in the air for 36h. After detection by TLC until the reaction was completed, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent to obtain a crude product, which was then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 10:1, silica gel Column flash column chromatography to obtain 4f of this example as a yellow solid 43.0mg, yield 55%.
57% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 16h; Irradiation; 31 In a 15mL reaction tube, the photocatalyst 2,4,5,6-tetra(9-carbazolyl)-isophthalonitrile (0.002 mmol), quinoxalinone 1a (0.2 mmol), 2-allyl bis Indole-1,3-dione 2m (0.4 mmol), sodium trifluoromethanesulfinate 3a (0.4 mmol), 1,4-dioxane/water (volume ratio 6:1) 4 mL, Mix well, and then react for 16 hours in the air at room temperature under the irradiation of a 3W blue LED lamp. After the reaction was detected by TLC until the reaction was completed, ethyl acetate was added and extracted 3 times. The extract was concentrated under vacuum (0.08Mpa) to solvent-free to obtain the crude product, and then used petroleum ether and ethyl acetate in a volume ratio of 3:1 The mixed eluent was washed with silica gel column and flash column chromatography to obtain 4m of this example, which was 47.3 mg of yellow solid, and the yield was 57%.
57% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 12h; Irradiation; 3. General procedure for visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na General procedure: To a solution of quinoxalin-2(H)-one 1 (0.1 mmol), CF3SO2Na 3 (0.2 mmol), 4CziPN (0.001 mmol, 1 mol %), 1,4-dioxane/H 2 O (6/1, 2.5 mL) was added alkene 2 (0.2 mmol). The reaction mixture was open to the air and stirred under the irradiation of 3 W blue LEDs at room temperature for 12 h. After completion of the reaction, the solution was concentrated in vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired product 4.

  • 86
  • [ 140-67-0 ]
  • [ 6479-18-1 ]
  • [ 2926-29-6 ]
  • 3-(4,4,4-trifluoro-1-(4-methoxyphenyl)butan-2-yl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; Sealed tube;
80% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; 2 Example 2 At room temperature, quinoxalinone 1a (0.2 mmol), p-methoxyallylbenzene (0.4 mmol), sodium trifluoromethylsulfinate (0.4 mmol), potassium peroxodisulfate ( 0.6mmol), acetonitrile: water (4:1) 2.5mL, mixed evenly, then stirred at 80°C in the air for 24h. After detection by TLC until the reaction was completed, the reaction solution was concentrated under vacuum (0.08Mpa) under reduced pressure to no solvent to obtain a crude product, which was then washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 10:1, silica gel Column flash column chromatography to obtain 4b of this example, as a yellow solid 60.0mg, yield 80%.
54% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 12h; Irradiation; 3. General procedure for visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na General procedure: To a solution of quinoxalin-2(H)-one 1 (0.1 mmol), CF3SO2Na 3 (0.2 mmol), 4CziPN (0.001 mmol, 1 mol %), 1,4-dioxane/H 2 O (6/1, 2.5 mL) was added alkene 2 (0.2 mmol). The reaction mixture was open to the air and stirred under the irradiation of 3 W blue LEDs at room temperature for 12 h. After completion of the reaction, the solution was concentrated in vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired product 4.
  • 87
  • [ 6479-18-1 ]
  • [ 405-99-2 ]
  • [ 2926-29-6 ]
  • 3-(3,3,3-trifluoro-1-(4-fluorophenyl)propyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 12h; Irradiation; 35 Add the photocatalyst 2,4,5,6-tetra(9-carbazolyl)-isophthalonitrile (0.002 mmol), quinoxalinone 1a (0.2 mmol), and p-fluorostyrene 2q into the 15mL reaction tube sequentially (0.4 mmol), sodium trifluoromethanesulfinate 3a (0.4 mmol), 1,4-dioxane/water (volume ratio 6:1) 4 mL, mix well, and then irradiate with 3W blue LED light In the air, react at room temperature for 12 hours. After the completion of the reaction was detected by TLC, ethyl acetate was added to extract 3 times, the extract was concentrated under vacuum (0.08 Mpa) to solvent-free, and the crude product was obtained, and then petroleum ether and ethyl acetate with a volume ratio of 10:1 Washing with mixed eluents and flash column chromatography on silica gel column to obtain 4q of this example as a yellow solid 52.5 mg, with a yield of 75%.
75% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In 1,4-dioxane; water at 20℃; for 12h; Irradiation; 3. General procedure for visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na General procedure: To a solution of quinoxalin-2(H)-one 1 (0.1 mmol), CF3SO2Na 3 (0.2 mmol), 4CziPN (0.001 mmol, 1 mol %), 1,4-dioxane/H 2 O (6/1, 2.5 mL) was added alkene 2 (0.2 mmol). The reaction mixture was open to the air and stirred under the irradiation of 3 W blue LEDs at room temperature for 12 h. After completion of the reaction, the solution was concentrated in vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired product 4.
41% With dipotassium peroxodisulfate In water; acetonitrile at 80℃; for 24h; Sealed tube;
  • 88
  • [ 6479-18-1 ]
  • [ 583-04-0 ]
  • 3-azido-2-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)propyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With [bis(acetoxy)iodo]benzene; trimethylsilylazide In acetonitrile at -10℃; for 12h; Schlenk technique; Inert atmosphere; Intermolecular Azidoheteroarylation of Alkenes; General Procedure General procedure: A Schlenk-tube equipped with a magnetic stir bar was charged with aquinoxalin2(1H)-one 2 (0.2 mmol), TMSN 3 (0.4 mmol, 2 equiv),PhI(OAc)2 (0.4 mmol, 2.0 equiv), and then evacuated and backfilledwith N2 for three times. Afterwards, an alkene 1 (0.4 mmol, 2.0 equiv)and CH3CN (1 mL) were added under N2 atmosphere. The reactionmixture in the closed Schlenk tube was stirred at -10 °C. After 12 h,the resulting mixture was extracted with CH2Cl2 (3 x 15 mL) and thecombined organic layers were dried (anhyd Na2SO4). After removal ofthe solvent under reduced pressure, the crude product was purifiedby column chromatography (eluent: PE:EA = 2:1) on silica gel to givethe product.
  • 89
  • [ 6479-18-1 ]
  • [ 591-80-0 ]
  • 5-azido-4-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)pentanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With [bis(acetoxy)iodo]benzene; trimethylsilylazide In acetonitrile at -10℃; for 12h; Schlenk technique; Inert atmosphere; Intermolecular Azidoheteroarylation of Alkenes; General Procedure General procedure: A Schlenk-tube equipped with a magnetic stir bar was charged with aquinoxalin2(1H)-one 2 (0.2 mmol), TMSN 3 (0.4 mmol, 2 equiv),PhI(OAc)2 (0.4 mmol, 2.0 equiv), and then evacuated and backfilledwith N2 for three times. Afterwards, an alkene 1 (0.4 mmol, 2.0 equiv)and CH3CN (1 mL) were added under N2 atmosphere. The reactionmixture in the closed Schlenk tube was stirred at -10 °C. After 12 h,the resulting mixture was extracted with CH2Cl2 (3 x 15 mL) and thecombined organic layers were dried (anhyd Na2SO4). After removal ofthe solvent under reduced pressure, the crude product was purifiedby column chromatography (eluent: PE:EA = 2:1) on silica gel to givethe product.
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