CN116120246A - 3-butyl-2 (1H) quinoxalinone compound and preparation method thereof - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
Abstract
The invention belongs to the technical field of medicine synthesis, and particularly relates to a 3-butyl-2 (1H) quinoxalinone compound and a preparation method thereof. The 2 (1H) quinoxalinone derivative and butyl lithium borate are used as raw materials, and react for 1-3 hours at room temperature under the irradiation of ruthenium catalytic blue light, so that the 3-butyl-2 (1H) quinoxalinone compound can be obtained by a one-step method, and the yield is 64-92%. The invention has the advantages that the universality of the substrate is higher, and various substrates can be well converted into target compounds no matter the substrates are electron-withdrawing groups or electron-donating groups; the post-reaction treatment is also very simple, and the 3-butyl-2 (1H) quinoxalinone compound can be prepared only by common column chromatography separation.
Description
Technical Field
The invention belongs to the technical field of medicine synthesis, and particularly relates to a 3-butyl-2 (1H) quinoxalinone compound and a preparation method thereof.
Background
Quinoxalinones are an important class of nitrogen-containing heterocyclic compounds, widely found in natural products and drug molecules, and widely used in anticancer, antibacterial and antiallergic drugs [ (a) Shen, q. -k.; gong, g.—h.; li, G; jin, m.; cao, l. -h; quan, z. -s.j.enzyme.inhib.med.chem.2020, 35,85 (b) Ji, y. -p; chen, x; chen, h.; zhang, x.; fan, z. -y; xie, L.—N.; ma, b; zhu, c. -j.biorg.med.chem.2019, 27,1658]. In particular, 3-alkylquinoxalinone parent cores are found in a number of biologically active molecules.
There are generally 2 methods for preparing quinoxalinones, one is by intermolecular cyclization between 1, 2-phenylenediamine and an acid or ester of an-keto acid, aldehyde to give [ (a) Yuan, J. -W.; fu, J.—H.; liu, s. -n; xiao, y.—m.; mao, p.; qu, l. -b.org.biomol.chem.,2018,16,3203; (b) K.yin and R.zhang, synlett,2018,29,597); another is direct functionalization of the quinoxalinone substrate ((a) Yuan, J.; fu, J.; yin, J.; dong, Z.; xiao, Y.; mao, P.; qu, L.org. chem. Front.; 2018,5,2820; b) Yang, L.; gao, P.; duan, X.; G U.Y.; R.; guo, L.N. org. Lett.; 2018,20,1034). In 2018, the cyclobutane oxime used in the SUANCHA Guo Lina subject group is directly subjected to cyanoalkylation on the C-3 position of a quinoxalinone substrate under the catalysis of iron, and the method still has the limitations that the reaction temperature is high, the catalyst dosage is large and some sensitive substrates are unsuitable [ Yang, L.; gao, p.; duan, X. -H.; gu, Y.—R.; guo, L. -N.direct C-HCyanoalkylation of Quinoxalin-2 (1H) -ones via Radical C-C Bond clear.org.Lett.2018, 20,1034]. In 2022, the group of the subject of Huaibei university Wang Min reported that a series of 3-alkyl quinoxalinone derivatives were synthesized with an aldehyde under the catalysis of the photocatalyst 9, 10-phenanthrenedione, but unfortunately no 3-butyl quinoxalinone derivative was obtained [ Wang, m.; liu, j.; zhang, y. -c; sun, P. -P.Adv.Synth.Catal.2022,364,2660]. Therefore, the development of a preparation method of the 3-butyl 2 (1H) quinoxalinone compound with high efficiency and mild temperature has important significance.
Disclosure of Invention
The invention provides a 3-butyl 2 (1H) quinoxalinone compound and a preparation method thereof.
The preparation method of the 3-butyl-2 (1H) quinoxalinone compound is shown as the following formula:
wherein R is 1 The method comprises the following steps: 6-hydrogen, 6-methyl, 6-methoxy, 6-nitro, 6-trifluoromethyl, 6-chloro, 6-phenyl, 6, 7-dimethyl;
R 2 the method comprises the following steps: n-propyl, n-pentyl, alkynyl,alkenyl groups.
The specific method comprises the following steps: under the protection of argon, adding 2 (1H) quinoxalinone derivative, butyllithium borate and ruthenium to catalyze and stir to react in the presence of alkaline condition in a 25mL test tube to generate pyrano [2,3-b ] quinoline alkaloid. After the reaction is completed, the reaction solution is concentrated, and the target product is obtained by flash column chromatography (petroleum ether and ethyl acetate are used as eluent).
Wherein, the reaction conditions are as follows: the reaction is carried out at room temperature under the catalysis of ruthenium and the irradiation of blue light for 1 to 3 hours.
The molar ratio of the raw material 2 (1H) quinoxalinone derivative to the tributyllithium salt is 1:1.5-1:3.
The solvent is acetonitrile, dichloromethane, tetrahydrofuran, methanol, and the alkali is sodium carbonate.
The ruthenium catalyst is terpyridyl ruthenium chloride and ruthenium trichloride trihydrate.
The structural formula of the 2 (1H) quinoxalinone derivative is shown in the following formula,
wherein R is 1 The method comprises the following steps: 6-hydrogen, 6-methyl, 6-methoxy, 6-nitro, 6-trifluoromethyl, 6-chloro, 6-phenyl, 6, 7-dimethyl;
R 2 the method comprises the following steps: n-propyl, n-pentyl, alkynyl, alkenyl.
The synthesis method of the butyl lithium borate comprises the following steps:
slowly adding butyl lithium into the mixed solution of the Boracene and the tetrahydrofuran at the temperature of-78 ℃ for 15 minutes; heating to room temperature and keeping at room temperature for 10 minutes, wherein TLC (thin layer chromatography) plate monitors the end of the reaction, the reaction liquid is recrystallized by tetrahydrofuran and normal hexane, and the obtained solid is washed by petroleum ether to obtain butyl lithium borate 2; the reaction formula is as follows:
the Boracene synthesis reaction is of the formula:
the invention has simple post-reaction treatment, and can obtain the pure 3-butyl-2 (1H) quinoxalinone compound by using the mixed solvent of petroleum ether and ethyl acetate as an eluent by a simple column chromatography separation method.
The invention has the advantages that: 3-butyl-2 (1H) quinoxalinone compounds are widely available in natural products and bioactive compounds and have wide application in medicine and pharmacology. According to the invention, the 2 (1H) quinoxalinone derivative and butyl lithium borate are used as raw materials for the first time, and 3-butyl-2 (1H) quinoxalinone is constructed by a one-step method at room temperature under blue light irradiation and ruthenium catalysis, and the yield is up to 64-92%.
Detailed Description
The structural formula of the reaction process and the obtained product is as follows:
example 1
To a 25mL tube was added the compound 1-methylquinoxalin-2 (1H) -one (0.5 mmol,80 mg), butyllithium salt 2 (0.75 mmol), terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL). The reaction was allowed to react at room temperature for 2 hours under blue light irradiation. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give 3a as a yellow solid in 82% yield. mp.47-48 ℃. 1 H NMR(300MHz,CDCl 3 )δ7.75(dd,J＝7.9,1.4Hz,1H),7.47-7.41(m,1H),7.28-7.20(m,2H),3.63(s,3H),2.87(t,J＝7.6,2H),1.75-1.65(m,2H),1.43-1.36(m,2H),0.90(t,J＝7.3Hz,3H).
The synthesis method of the butyl lithium borate comprises the following steps:
to a solution of Boracene (540 mg,2.0 mmol) in tetrahydrofuran (20 mL) at-78deg.C was slowly added butyllithium (1.6M n-hexane, 1.3mL,2.02 mmol) and the mixture was dropped over 15 minutes. Slowly warm to room temperature and hold at room temperature for 10 minutes, TLC plate monitored the end of the reaction. The reaction solution was recrystallized from tetrahydrofuran and n-hexane, and the obtained solid was washed with petroleum ether to obtain butyllithium borate.
The synthetic method of the borene comprises the following steps: 1, 3-dichlorobenzene (1.68 g,11.5 mmol) and tetrahydrofuran (25 mL) were added to a 100mL three-necked flask under argon atmosphere, and n-butyllithium (6mL,2M in hexanes) was slowly added at 78 ℃. After maintaining the temperature for 2 hours, the grignard reagent (8.5 g,40.3 mmol) was added and the mixture was slowly warmed to room temperature and then heated under reflux for 18 hours. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give intermediate m in 90% yield.
In a 100mL three-necked flask, intermediate m (11 mmol) and o-dichlorobenzene (22 mL) were added at 0deg.C, BBr 3 (16.5 mmol,1.5 eq). The reaction was kept in ice bath, N-diisopropylethylamine was added after 18 hours, the reaction was slowly warmed to room temperature and then heated to reflux overnight, after completion of the reaction by TLC plate monitoring, the reaction solution was poured into water, extracted with chloroform, the organic phases were combined and dried over anhydrous sodium sulfate, and the organic layer was concentrated to give borene by flash column chromatography (petroleum ether and ethyl acetate as eluent) in 88% yield.
Example 2
To a 25mL tube was added the compound 1, 6-dimethylquinoxalin-2 (1H) -one (0.5 mmol,87 mg), butyllithium salt 2 (0.75 mmol), terpyridyl ruthenium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL). The reaction was allowed to react at room temperature for 3 hours under blue light irradiation. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give 3b as a yellow solid in 79% yield. mp 167-168 ℃. 1 H NMR(400MHz,CDCl 3 )δ8.12(d,J＝8.0Hz,1H),7.70(t,J＝7.6Hz,1H),7.57-7.52(m,3H),7.48-7.45(m,1H),7.29(d,J＝8.4Hz,2H),7.21-7.17(m,1H),7.09(d,J＝8.0Hz,1H),6.74-6.69(m,2H),5.35(s,2H).
Example 3
6-methoxy 1-methylquinoxalin-2 (1H) -one (0.5 mmol,95 mg), butyllithium salt 2 (0.75 mmol) were added to a 25mL tube,terpyridyl ruthenium chloride (1 mmol%), sodium carbonate (10.6 mg) and acetonitrile (2 mL). After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give 3c as a yellow solid in 80% yield. mp 66-67 ℃. 1 H NMR(400MHz,CDCl 3 )δ7.32(d,J＝8.0,Hz,1H),7.28-7.21(m,1H),7.17-7.13(m,2H),3.89(s,3H),3.70(s,3H),2.96(t,J＝7.6,2H),1.83-1.72(m,2H),1.52-1.45(m,2H),0.99(t,J＝7.3Hz,3H).
Example 4
6-Nitro-1-methylquinoxalin-2 (1H) -one (0.5 mmol,102.5 mg), butyllithium salt 2 (0.75 mmol), ruthenium terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL) were added to a 25mL tube. After completion of the reaction, the reaction solution was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give a yellow solid 3d in 72% yield. mp 141-142 ℃. 1 H NMR(400MHz,CDCl 3 )δ8.20(d,J＝2.3Hz,1H),8.17(dd,J＝8.7,2.3Hz,2H),7.96(d,J＝8.6Hz,1H),3.77(s,3H),3.03-2.95(m,2H),1.79(tt,J＝7.7,6.6Hz,2H),1.48(q,J＝7.5Hz,2H),0.98(t,J＝7.4Hz,3H).
Example 5
6-trifluoromethyl 1-methylquinoxalin-2 (1H) -one (0.5 mmol,114 mg), butyllithium salt 2 (0.75 mmol), ruthenium terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL) were added to a 25mL tube. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give 3e as a yellow solid in 73% yield. mp 145-146 ℃. 1 H NMR(400MHz,CDCl 3 )δ7.93(d,J＝8.2Hz,1H),7.57(dd,J＝8.3,1.8Hz,1H),7.53(d,J＝1.8Hz,1H),3.74(s,3H),3.01-2.94(m,2H),1.83-1.73(m,2H),1.47(dt,J＝14.8,7.4Hz,2H),0.98(t,J＝7.3Hz,3H).
Example 6
6-chloro 1-methylquinoxalin-2 (1H) -one (0.5 mmol,97 mg), butyllithium salt 2 (0.75 mmol), terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL) were added to a 25mL tube. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give 3f as a yellow solid,the yield was 92%. mp 91-92 ℃. 1 H NMR(400MHz,CDCl 3 )δ7.66(d,J＝9.2Hz,1H),7.24-7.17(m,2H),3.59(s,3H),2.91-2.79(m,2H),1.74-1.63(m,3H),1.44-1.34(m,2H),0.89(t,J＝7.4Hz,3H).
Example 7
6-phenyl-1-methylquinoxalin-2 (1H) -one (0.5 mmol,118.1 mg), butyllithium salt 2 (0.75 mmol), ruthenium terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL) were added to a 25mL tube. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give 3g of a white solid with a yield of 74%. mp 74-76 ℃. 1 H NMR(400MHz,CDCl 3 )δ7.79(d,J＝8.4Hz,1H),7.57-7.56(m,2H),7.47(dd,J＝8.4,1.8,1H),7.43-7.39(m,2H),7.36-7.31(m,2H),3.67(s,3H),2.88(t,J＝7.6,2H),1.74-1.67(m,2H),1.43-1.37(m,2H),0.90(t,J＝7.3Hz,3H).
Example 8
1-n-propylquinoxalin-2 (1H) -one (0.5 mmol,94 mg), butyllithium salt 2 (0.75 mmol), terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL) were added to a 25mL tube. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give a colorless liquid in 74% yield for 3 h. 1 H NMR(400MHz,CDCl 3 )δ7.83(dd,J＝7.9,1.6Hz,1H),7.50(m,1H),7.37-7.25(m,2H),4.26-4.18(m,2H),2.99-2.92(m,2H),1.83-1.73(m,4H),1.48(h,J＝7.4Hz,2H),1.05(t,J＝7.4Hz,3H),0.98(t,J＝7.3Hz,3H).
Example 9
1-n-pentylquinoxalin-2 (1H) -one (0.5 mmol,108 mg), butyllithium salt 2 (0.75 mmol), terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL) were added to a 25mL tube. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give colorless liquid 3i in 80% yield. 1 H NMR(400MHz,CDCl 3 )δ7.75(dd,J＝7.9,1.4Hz,1H),7.45-7.40(m,1H),7.25-7.20(m,2H),4.15(t,J＝8.1,2H),2.86(t,J＝7.7,2H),1.69-1.64(m,4H),1.44-1.34(m,6H),0.89(t,J＝7.3Hz,3H),0.85(t,J＝7.4Hz,3H).
Example 10
1-allylquinoxalin-2 (1H) -one (0.5 mmol,93 mg), butyllithium salt 2 (0.75 mmol), terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL) were added to a 25mL tube. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give 3j as a pale yellow liquid in 73% yield. 1 H NMR(400MHz,CDCl 3 )δ7.75(dd,J＝7.9,1.2Hz,1H),7.42-7.38(m,1H),7.26-7.22(m,1H),7.19(d,J＝8.4,1H),5.91-5.81(m,1H),5.18(d,J＝10.4Hz,1H),5.10-5.06(m,1H),4.84-4.82(m,2H),2.88(t,J＝7.7Hz,2H),1.72-1.67(m,2H),1.43-1.37(m,2H),0.90(t,J＝7.3Hz,3H).
Example 11
1-Proynylquinoxalin-2 (1H) -one (0.5 mmol,92 mg), butyllithium salt 2 (0.75 mmol), terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL) were added to a 25mL tube. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give 3k as a pale yellow solid in 64% yield. mp 86-87 ℃. 1 H NMR(400MHz,CDCl 3 )δ7.77(dd,J＝8.0,1.4Hz,1H),7.49-7.45(m,1H),7.38-7.36(m,1H),7.31-7.26(m,1H),4.97(d,J＝2.6,2H),2.87(t,J＝7.7Hz,2H),2.21(t,J＝2.5Hz,1H),1.72-1.66(m,2H),1.43-1.37(m,2H),0.90(t,J＝7.4Hz,3H).
Example 12
1,6, 7-trimethylquinoxalin-2 (1H) -one (0.5 mmol,94 mg), butyllithium salt 2 (0.75 mmol), ruthenium terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL) were added to a 25mL tube. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give 3l of yellow solid in 64% yield. mp is 83-85 ℃. 1 H NMR(300MHz,CDCl 3 )δ7.51(s,1H),6.97(s,1H),3.60(s,3H),2.84(t,J＝7.6,2H),2.33(s,3H),2.26(s,3H),1.73-1.66(m,2H),1.42-1.35(m,2H),0.89(t,J＝7.3Hz,3H).
Example 13
1 benzyl quinoxalin-2 (1H) -one (0.5 mmol,219.1 mg), butyllithium salt 2 (0) were added to a 25mL tube.75 mmol), terpyridyl ruthenium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL). After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give a white solid 3m in 71% yield. mp 94-95 ℃. 1 H NMR(400MHz,CDCl 3 )δ8.19-8.10(m,2H),8.01-7.91(m,3H),7.83(dd,J＝8.2,1.5Hz,1H),7.72-7.51(m,6H),5.65(s,2H),3.84(s,3H),3.09-3.01(m,2H),1.82(tt,J＝7.8,6.6Hz,2H),1.48(h,J＝7.4Hz,2H),0.97(t,J＝7.4Hz,3H).
3m are useful as angiotensin II receptor antagonists.
Comparative example 1
To a 25mL tube was added the compound 1-methylquinoxalin-2 (1H) -one (0.5 mmol,80 mg), butyllithium salt 2 (0.75 mmol), terpyridinium chloride (1 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL). The reaction was stirred for 2 hours under light protection. The reaction was detected by TLC plate and found to be non-reactive.
Comparative example 2
To a 25mL tube was added the compound 1-methylquinoxalin-2 (1H) -one (0.5 mmol,80 mg), butyllithium salt 2 (0.75 mmol), sodium carbonate (10.6 mg) and acetonitrile (2 mL). The reaction was allowed to react for 2 hours under blue light irradiation. The reaction was monitored by TLC plates and found to be non-reactive.
Comparative example 3
To a 25mL tube was added the compound 1-methylquinoxalin-2 (1H) -one (0.5 mmol,80 mg), butyllithium salt 2 (0.75 mmol), terpyridinium chloride (1 mmol%) and acetonitrile (2 mL). The reaction was allowed to react for 2 hours under blue light irradiation. After completion of the reaction, the reaction mixture was concentrated by TLC plate and flash column chromatography (petroleum ether and ethyl acetate as eluent) to give 3a as a yellow solid in 26% yield.
The examples are preferred embodiments of the present invention, but the present invention is not limited to the above-described embodiments, and any obvious modifications, substitutions or variations that can be made by one skilled in the art without departing from the spirit of the present invention are within the scope of the present invention.
Claims (8)
1. A 3-butyl-2 (1H) quinoxalinone compound, wherein the compound has the structure:
wherein R is 1 The method comprises the following steps: hydrogen, methyl, methoxy, nitro, trifluoromethyl, chloro, phenyl, 6, 7-dimethyl, R 2 The method comprises the following steps: n-propyl, n-pentyl, alkynyl, alkenyl.
2. A process for the preparation of 3-butyl-2 (1H) quinoxalinone compounds according to claim 1, said process comprising: taking 2 (1H) quinoxalinone derivative and butyllithium borate as raw materials, and stirring and reacting in the presence of a solvent under an alkaline condition to generate pyrano [2,3-b ] quinoline alkaloid;
wherein, the reaction conditions are as follows: the reaction is carried out for 1 to 3 hours at room temperature under the catalysis of ruthenium and the irradiation of blue light.
3. The method for preparing 3-butyl-2 (1H) quinoxalinone compound according to claim 2, wherein the solvent is acetonitrile, dichloromethane, tetrahydrofuran, methanol; the base is sodium carbonate.
4. The method for preparing 3-butyl-2 (1H) quinoxalinone compound according to claim 2, wherein the ruthenium-catalyzed catalyst is terpyridyl ruthenium chloride or ruthenium trichloride trihydrate.
5. The method for producing a 3-butyl-2 (1H) quinoxalinone compound according to claim 2, wherein the structural formula of said 2 (1H) quinoxalinone derivative is as follows,
wherein R is 1 The method comprises the following steps: 6-hydrogen, 6-methyl, 6-methoxy, 6-nitro,6-trifluoromethyl, 6-chloro, 6-phenyl, 6, 7-dimethyl, R 2 The method comprises the following steps: n-propyl, n-pentyl, alkynyl, alkenyl.
6. The method for preparing 3-butyl-2 (1H) quinoxalinone compound according to claim 2, wherein said butyllithium borate has the following structure:
7. the method for preparing 3-butyl-2 (1H) quinoxalinone compound according to claim 2, wherein the synthesis method of butyl lithium borate is as follows: butyl lithium is added into the mixed solution of the Boracene and the tetrahydrofuran at the temperature of minus 78 ℃ for 15 minutes; heating to room temperature and keeping for 10 minutes, wherein a TLC (thin layer chromatography) plate monitors the end of the reaction, the reaction liquid is recrystallized by tetrahydrofuran and normal hexane, and the obtained solid is washed by petroleum ether to obtain butyl lithium borate 2; the reaction formula is as follows:
8. the method for preparing 3-butyl-2 (1H) quinoxalinone compound according to claim 2, wherein the molar ratio of the 2 (1H) quinoxalinone derivative to the tributyllithium salt is 1:1.5-1:3.
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