* 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.
General procedure: A mixture of sodium (1 mmol, 0.023 g) and alcohol (3 mL) was stirred for 15 min at room temperature. Then 2,3-dichloroquinoxaline (1 mmol, 0.199 g) was added to the mixture until the complete consumption of the starting materials, monitored by TLC. After evaporation of the solvent, the resulting precipitate was washed with H2O; it did not require any further purification.
Reference Example 20 To a suspension of 2,3-dichloroquinoxaline (300 mg, 1.51 mmol) in methanol (15 mL) and N,N-dimethylformamide (1.0 mL) was added sodium methoxide (28percent in methanol, 309 mg, 1.66 mmol) dropwise at 0 0C. After being stirred for 2 hour at room temperature, the reaction mixture was concentrated in vacuo. The residue was diluted with chloroform and water. The organic layer was separated with phase separator and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane: ethyl acetate = 19: 1) to give 2-chloro-3-methoxyquinoxaline (the compound of Reference Example 20 listed in Table of Reference Example as described hereinafter) as a colorless powder (251 mg,percent).
Reference：
[1] Molecules, 2012, vol. 17, # 7, p. 7737 - 7757
[2] Journal of the Chemical Society, 1955, p. 1804,1806
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 1035,1038
[4] Patent: US2005/148586, 2005, A1, . Location in patent: Page/Page column 19
[5] RSC Advances, 2016, vol. 6, # 87, p. 83901 - 83908
4
[ 124-41-4 ]
[ 87885-47-0 ]
[ 32998-25-7 ]
Reference：
[1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
5
[ 15804-19-0 ]
[ 32998-25-7 ]
Reference：
[1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[2] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[3] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[4] Medicinal Chemistry Research, 2013, vol. 22, # 4, p. 1660 - 1673
6
[ 2213-63-0 ]
[ 32998-25-7 ]
Reference：
[1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[2] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[3] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
7
[ 34117-90-3 ]
[ 32998-25-7 ]
Reference：
[1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
In tetrahydrofuran; methanol; at 0 - 20℃; for 1.5h;
To a solution of 2,3-dichloro-quinoxaline (500 mg, 2.51 mmol) in THF (5 mL) at 0 C. was added sodium methoxide (0.57 mL of a 25% solution in methanol, 2.51 mmol) dropwise. The reaction was stirred at 0 C. for 30 min then warmed to room temperature or 1 h. The reaction mixture was diluted with dichloromethane, washed with brine, dried (MgSO4), and concentrated in vacuo to give compound 76 as a yellow solid.
Reference Example 20 To a suspension of 2,3-dichloroquinoxaline (300 mg, 1.51 mmol) in methanol (15 mL) and N,N-dimethylformamide (1.0 mL) was added sodium methoxide (28% in methanol, 309 mg, 1.66 mmol) dropwise at 0 0C. After being stirred for 2 hour at room temperature, the reaction mixture was concentrated in vacuo. The residue was diluted with chloroform and water. The organic layer was separated with phase separator and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane: ethyl acetate = 19: 1) to give 2-chloro-3-methoxyquinoxaline (the compound of Reference Example 20 listed in Table of Reference Example as described hereinafter) as a colorless powder (251 mg,%).
INTERMEDIATE: 4-Chloro-l -(2-chloro-phenyl)-[l ,2,4]triazolo[4,3-a]quinoxaline (IIx). A mixture of <strong>[32998-25-7]2-chloro-3-methoxyquinoxaline</strong> (455 mg) and 2-chlorobenzhydrazide (439 mg) in acetonitrile (10 mL) was heated at 150 C for 15 min under MW conditions. The reaction mixture was cooled in an ice/water bath and the precipitated solid was collected by filtration. This material was suspended in acetonitrile (10 mL) and phosphoryl chloride (1.09 mL) was added. The mixture was heated at 150 C for lh under MW conditions, before another 0.5 mL of phosphoryl chloride was added and the mixture was heated for an additional lh at 150 C under MW conditions. The reaction mixture was poured onto ice and diluted with ice/water to a final volume of 50 mL. It was neutralized with solid NaHC03 and the resulting yellow precipitate was collected by filtration, water and dried to afford IIx (409 mg).
General procedure: A mixture of sodium (1 mmol, 0.023 g) and alcohol (3 mL) was stirred for 15 min at room temperature. Then 2,3-dichloroquinoxaline (1 mmol, 0.199 g) was added to the mixture until the complete consumption of the starting materials, monitored by TLC. After evaporation of the solvent, the resulting precipitate was washed with H2O; it did not require any further purification.
General procedure: A mixture of sodium (1 mmol) and an alcohol (3 mL) was stirred for 15 min at room temperature. Then 2,3-dichloroquinoxaline (1 mmol) was added to the mixture until the complete consumption of the starting materials (monitored by TLC). After evaporation of the solvent, the resulting precipitate was washed with H2O; it did not require any further purification.
4-methoxy-1-(morpholin-4-yl)pyrrolo[1,2-a]quinoxaline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75%
General procedure: A mixture of a 3-substituted-2-chloroquinoxaline 2(1 mmol), a secondary amine (3 mmol), Pd(PPh3)2Cl2 (0.05 mmol,0.036 g), CuI (0.1 mmol, 0.019 g), sodium dodecyl sulfate (0.1 mmol,0.029 g), and K2CO3 (3 mmol, 0.414 g) was stirred in H2O (5 mL) at room temperature under an argon atmosphere. Propargyl alcohol(1.2 mmol, 0.067 g) was then added, and the resulting mixture was stirred at 80 C for 18 h. After completion of the reaction, the mixture was filtered, and the resulting solid was washed with H2O and dried. The crude product was purified by column chromatography (silica gel 100) using CHCl3-CH3OH (99:1) as the eluent.
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