Preparation method of 3-methylquinoxaline-2(1H)-one compounds

A kind of methylquinoxalinone, methylquinoxaline technology, applied in the field of synthesis of quinoxalinone derivatives, can solve the direct methylation of quinoxalin-2(1H)-one compound C3 position There are no related reports and other problems, and the effects of good applicability, reduction of reaction cost and energy consumption, and high reaction efficiency are achieved.

Inactive Publication Date: 2019-07-09
HUNAN UNIV OF SCI & ENG
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0005] At present, the arylation, acylation, phosphorylation, amination and trifluoromethylation of quinoxaline-2(1H)-one at the C3 position have been reported, but about quinoxaline-2(1H) -Direct methylation of the C3 position of ketone compounds has not been reported yet

Method used

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  • Preparation method of 3-methylquinoxaline-2(1H)-one compounds
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  • Preparation method of 3-methylquinoxaline-2(1H)-one compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]

[0038] At 25°C, in a 10mL reaction tube, sequentially add 1-methylquinoxaline-2(1H)-one 1a (0.2mmol), iodobenzene diacetate 2a (0.44mmol), Ru(bpy) 3 Cl 2 ·6H 2 O (0.002mmol), PEG-200 (1mL), mixed evenly, and then stirred and reacted for 8h under the irradiation of 12w white LED lamp. After the reaction was detected by TLC, cyclopentyl methyl ether (2ml×3) was added for extraction, and the upper layer extract was taken and concentrated in vacuum at 50°C until there was no solvent to obtain a crude product, which was then extracted with petroleum ether at a volume ratio of 2:1 Flush with ethyl acetate mixed eluent, silica gel column flash column chromatography, obtain 1,3-dimethylquinoxalin-2 (1H)-one product 3aa in this example, be white solid 32.8mg, yield 91%.

[0039] The obtained product nuclear magnetic spectrum data are: 1 H NMR (400MHz, CDCl 3 ):δ=7.80(d,J=8.0Hz,1H),7.54–7.50(m,1H),7.35–7.29(m,2H),3.70(s,3H),2.60(s,3H); 13 C NMR (100MHz, CDCl 3 ): δ=158....

Embodiment 2

[0041]

[0042] At 25°C, in a 10mL reaction tube, add 6-bromo-1-methylquinoxaline-2(1H)-one 1b (0.2mmol), iodobenzene diacetate 2a (0.44mmol), Ru(bpy ) 3 Cl 2 ·6H 2 O (0.002mmol), PEG-200 (1mL), mixed evenly, and then stirred and reacted for 8h under the irradiation of 12W white LED lamp. After the reaction was detected by TLC, cyclopentyl methyl ether (2ml×3) was added for extraction, and the upper layer extract was taken and concentrated in vacuum at 50°C until there was no solvent to obtain a crude product, which was then extracted with petroleum ether at a volume ratio of 2:1 Wash with ethyl acetate mixed eluent, silica gel column flash column chromatography, obtain 6-bromo-1,3-dimethylquinoxalin-2(1H)-one product 3ba in this example, be white solid 42.8 mg, yield 85%.

[0043] The obtained product nuclear magnetic spectrum data are: 1 H NMR (400MHz, CDCl 3 ): δ=7.94(d, J=2.0Hz, 1H), 7.60(dd, J 1 =8.8Hz,J 2 =2.0Hz, 1H), 7.16(d, J=8.8Hz, 1H), 3.67(s, 3H), 2.59(s,...

Embodiment 3

[0046]

[0047] At 25°C, in a 10mL reaction tube, add 7-fluoro-1-methylquinoxaline-2(1H)-one 1c (0.2mmol), iodobenzene diacetate 2a (0.44mmol), Ru(bpy ) 3 Cl 2 ·6H 2 O (0.002mmol), PEG-200 (1mL), mixed evenly, and then stirred and reacted for 6h under the irradiation of 12W white LED lamp. After the reaction was detected by TLC, cyclopentyl methyl ether (2ml×3) was added for extraction, and the upper layer extract was taken and concentrated in vacuum at 50°C until there was no solvent to obtain a crude product, which was then extracted with petroleum ether at a volume ratio of 2:1 Wash with ethyl acetate mixed eluent, silica gel column flash column chromatography, obtain 7-fluoro-1,3-dimethylquinoxalin-2 (1H)-one product 3ca in this example, be white solid 35.3 mg, yield 92%.

[0048] The obtained product nuclear magnetic spectrum data are: 1 H NMR (400MHz, CDCl 3 ):δ=7.79–7.76(m,1H),7.07–7.02(m,1H),6.98(dd,J 1 =10.0Hz,J 2 =2.4Hz,1H),3.66(s,3H),2.57(s,3H); 13 C NMR...

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Abstract

The invention discloses a preparation method of 3-methylquinoxaline-2(1H)-one compounds. The preparation method comprises the step of performing a visible light catalytic reaction on a quinoxaline ketone compound and iodobenzene diacetate under the action of a photocatalyst so as to obtain 3-methylquinoxaline ketone compounds. Compared with the prior art, the synthesis method has the advantages that (1) the adopted quinoxaline-2(1H)-one derivative raw material is cheap and easily available so that reduction of the cost is facilitated; (2) the reaction can be carried out under irradiation at room temperature, the conditions are mild, and the product is obtained in one step, so that the reaction yield is high, the operation is environmentally friendly, and industrial production is facilitated; and (3) the method has good applicability to functional groups, and multiple 3-methylquinoxaline ketone compound derivatives can be obtained.

Description

technical field [0001] The present invention relates to a kind of synthetic method of quinoxalinone derivatives, particularly relate to using quinoxalin-2(1H)-ketone compound and iodobenzene diacetate as starting materials, under the action of photocatalyst, through photocatalysis A method for preparing 3-methylquinoxalin-2(1H)-one in one step belongs to the technical field of organic synthesis. Background technique [0002] The methyl group is the smallest alkyl segment, which is found in most drug molecules. The introduction of a methyl group in the molecule can improve the drug solubility, selectivity and metabolic activity of the drug molecule. The introduction of a methyl group at the adjacent position of the metabolic site creates steric hindrance, which can prolong the half-life of the drug, such as simvastatin. If the half-life of the drug is too long, medicinal chemists can also generate a new metabolic site by introducing a methyl group to shorten the drug. Half-l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/44
CPCC07D241/44
Inventor 彭莎唐琳俐李碧岚邹丽管宗源
Owner HUNAN UNIV OF SCI & ENG
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