CN110590684A - Synthetic method of 3-alkylthio substituted quinoxalinone derivative - Google Patents
Synthetic method of 3-alkylthio substituted quinoxalinone derivative Download PDFInfo
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- CN110590684A CN110590684A CN201911026070.3A CN201911026070A CN110590684A CN 110590684 A CN110590684 A CN 110590684A CN 201911026070 A CN201911026070 A CN 201911026070A CN 110590684 A CN110590684 A CN 110590684A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
Abstract
The invention discloses a synthesis method of a 3-alkylthio substituted quinoxalinone derivative. The synthesis method comprises the following steps: under the illumination of certain wavelength, under the condition that a proper amount of photocatalyst exists or no photocatalyst is needed, an additive is added, and the quinoxaline-2-ketone compound and the thiol compound which are used as raw materials are used for synthesizing the 3-alkylthio substituted quinoxalinone derivative in high yield. Has the advantages of simple process, mild reaction condition, high purity and yield, and the like. The method has the advantages of cheap raw materials and catalyst, environmental protection, wider application compared with the traditional process, and avoidance of the use of metal catalyst.
Description
Technical Field
The invention relates to a synthesis method of 3-alkylthio substituted quinoxalinone derivatives, in particular to a synthesis method of 3-alkylthio substituted quinoxalinone derivatives, which synthesizes the 3-alkylthio substituted quinoxalinone derivatives by irradiating reactants with a light source with a certain wavelength in the presence of or without a photocatalyst.
Background
The quinoxaline derivative is an important natural compound, is an important aromatic nitrogen heterocyclic compound containing a benzopyrazine structure, has good biological activity, particularly the 3-substituted quinoxalinone has various drug effects and is mainly used as an enzyme inhibitor to treat various diseases, such as cancer, diabetes, thrombus and the like, in addition, the 3-substituted quinoxalinone also has antibacterial effect and has the functions of enzyme inhibitor, receptor antagonist and the like, and the uniqueness of the 3-substituted quinoxalinone structure ensures that the 3-substituted quinoxalinone also plays an important role in the fields of organic synthesis and organic materials, and the synthesis of the 3-substituted quinoxalinone also becomes a hot topic researched by chemists based on the wide application of the 3-substituted quinoxalinone in the field of medicines.
In 2004, according to the report of a. Carta: (Eur. J. Med. Chem.2004, 39 195- & ltSUB & gt 203.), and the 6, 7-difluoro-3-methyl-2-thiophenyl/phenylsulfinyl/benzenesulfonyl-quinoxaline-1, 4-dioxide obtained by screening is measured, so that the quinoxaline 1, 4-dioxide C-3-thio structure scaffold has the activity of resisting tuberculosis and candida.
2008, report from B. Yang: (Eur. J. Pharmacol.2008, 581,262-269.) shows that Q39 (3- (4-bromophenyl) -2- (ethylsulfonyl) -6-methylquinoxaline-1, 4-dioxide) can induce cancer cell apoptosis, has strong antiproliferative effect in vitro, has good anticancer activity in hypoxia specific cancer cells, and reflects the function of C-3 thio-structure quinoxaline derivative in biological medicine.
Therefore, the quinazoline ketone C-3 position of the sulfide etherification method is gradually receiving attention, but to the literature, synthesis of 3-alkylthio substituted quinazoline ketone derivatives literature reports are not rare, C-3 dehalogenation coupling is the most common method (Eur. J. Org. Chem.2013, 11, 2091–2105）。
The method utilizes the C-3 halogenated quinoxaline-2-ketone and a sulfhydryl compound to carry out reflux reaction for 0.5 to 4 hours in an ethanol/sodium alkoxide system, and carries out dehalogenation coupling to form a corresponding 3-alkylthio substituted quinoxaline derivative. However, the method needs to introduce halogen at the C-3 position for pre-functionalization, which does not conform to the principle of atom economy, and the rare earth metal catalyst is introduced in the reaction process, so that the method is difficult to meet the requirements of environmental protection.
With the continuous development of chemical technology, a simpler, more convenient and more environment-friendly synthesis method is explored to become a hotspot, and in view of high atom economy of Cross Dehydrogenation Coupling (CDC) reaction, the synthesis method is one of the most direct and most effective methods for constructing C-S bonds at present.
Disclosure of Invention
In view of the above problems in the prior art, the present invention aims to provide a method for synthesizing 3-alkylthio substituted quinoxalinone derivatives with short reaction time, simple operation, high product purity and high yield.
The synthesis method of the 3-alkylthio substituted quinoxalinone derivative is characterized in that a quinoxaline-2-ketone compound shown in a formula (II), a thiol compound shown in a formula (III) and an additive are added into an organic solvent according to a certain proportion, the mixture is stirred and reacts for 6 to 30 hours at 10 to 40 ℃ under the irradiation of a light source in the presence or absence of a photocatalyst, TLC (thin layer chromatography) tracks until the reaction of the quinoxaline-2-ketone compound serving as a raw material is completely finished, and the target compound 3-alkylthio substituted quinoxalinone derivative shown in the formula (I) is obtained through post-treatment;
wherein: r1Is C2 ~ C14 alkyl, phenethyl, 3-mercaptopropyl or allyl, R2Is hydrogen, methyl, halogen or nitro, the substituent R2Mono-or di-substituted independently or in any combination.
The synthesis method of the 3-alkylthio substituted quinoxalinone derivative is characterized in that the additive is cesium carbonate, potassium carbonate, trifluoroacetic acid, trifluoromethanesulfonic acid, sulfuric acid or acetic acid, and preferably trifluoroacetic acid, trifluoromethanesulfonic acid, sulfuric acid or acetic acid.
The synthesis method of the 3-alkylthio substituted quinoxalinone derivative is characterized in that the photocatalyst is Ru (bpy)3Cl3、Ir(ppy)3Rose bengal, eosin Y,Methylene blue or rhodamine 6G, preferably eosin Y, methylene blue or rhodamine 6G.
The synthesis method of the 3-alkylthio substituted quinoxalinone derivative is characterized in that the organic solvent is selected from one or the combination of any several of the following solvents: acetonitrile, DMF, toluene, thiols and DMSO, wherein the feeding amount of the organic solvent and the feeding ratio of the quinoxaline-2-ketone compound shown in the raw material formula (II) are 1.0: 5.0-30, preferably 1.0: 5.0-25, wherein the mercaptan is selected from ethanethiol, tert-butylthiol, heptanethiol or phenethyl thiol.
The synthesis method of the 3-alkylthio substituted quinoxalinone derivative is characterized in that the light source is blue light, white light or green light, and preferably the blue light.
The synthesis method of the 3-alkylthio substituted quinoxalinone derivative is characterized in that the mass ratio of the quinoxaline-2-ketone compound, the thiol compound, the additive and the photocatalyst is 1.0: 5.0-30: 2.0-4.0: 0.01 to 0.3, preferably 1.0: 5.0-25: 2.0-3.0: 0.01 to 0.2.
The synthesis method of the 3-alkylthio substituted quinoxalinone derivative is characterized in that the reaction time is 6-30 hours; the reaction temperature is 10-40 ℃.
The synthesis method of the 3-alkylthio substituted quinoxalinone derivative is characterized in that a developing solvent tracked by TLC is a mixture of a solvent and a solvent, wherein the solvent is a mixture of a solvent and a solvent, and the volume ratio of the developing solvent is 5: 1 petroleum ether and ethyl acetate.
The invention particularly recommends that the synthesis method of the 3-alkylthio substituted quinoxalinone derivative is carried out according to the following steps:
adding a compound (II) quinoxaline-2-ketone, a photocatalyst (IV) with a mass ratio of (0.01-0.2) to the compound (II), a compound (III) with a mass ratio of (5.0-25) to the compound (II), an additive (V) with a mass ratio of (2.0-3.0) to the compound (II), dissolving in an excellent organic solvent, irradiating the mixture under 3W blue light, stirring at 10-40 ℃ for reaction for 6-30 hours, and reacting the mixture with saturated NaHCO after the reaction is finished3Aqueous solution quenchingAnd (5) extinguishing and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to obtain a pure product.
By adopting the technology, compared with the prior art, the invention has the beneficial effects that:
the method adopts cheap photocatalyst or does not need the photocatalyst for reaction, has simple operation, mild reaction condition, short reaction time, high product purity and yield and more substrate applicability.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto.
Example 17-bromo-3- (ethylsulfanyl) -1-methylquinolin-2 (1H) -one (I-a)
In a 50mL open round bottom flask equipped with a magnetic stir bar was added compound (II) 7-bromo-1-methylquinoxalin-2-one (95.2 mg, 0.4 mmol), rhodamine 6G (9.6 mg, 0.02 mmol), ethanethiol (124.3 mg, 2mmol), trifluoroacetic acid (91 mg, 0.8mmol), the mixture was dissolved in DMF (5 mL), the reaction was stirred for 24 hours at 25 ℃ under 3W blue light irradiation, the reaction mixture was saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to obtain 88.03mg of the product 7-bromo-3- (ethylsulfanyl) -1-methylquinolin-2 (1H) -one (I-a) in 74.1% yield with an HPLC purity of 97.6%.
Example 26-bromo-3- (isopropylsulfanyl) -1-methylquinolin-2 (1H) -one (I-b)
In a 50mL open round bottom flask equipped with a magnetic stir bar was added compound (II) 6-bromo-1-methylquinoxalin-2-one (95.2 mg, 0.4 mmol), methylene blue (6.4 mg, 0.02 mmol), isopropylmercaptan (304.6 mg, 4 mmol), acetic acid (48 mg, 0.8mmol), DMSO (5 mL) was added to the mixture, irradiated with 3W of blue light, 1WThe reaction was stirred at 0 ℃ for 16 h and the reaction mixture was taken up with saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to give 90.6mg of product in 72.6% yield with HPLC purity 98.6%.
Example 36, 7-dichloro-3- (tert-butylsulfanyl) -1-methylquinolin-2 (1H) -one (I-c)
In a 50mL open round bottom flask equipped with a magnetic stir bar was added compound (II) 6, 7-dichloro-1-methylquinoxalin-2-one (90.8 mg, 0.4 mmol), rhodamine 6G (9.6 mg, 0.02 mmol), tert-butylmercaptan (541.1 mg, 6 mmol), trifluoromethanesulfonic acid (120 mg, 0.8mmol), the mixture was irradiated with 3W of blue light, the reaction was stirred at 30 ℃ for 16 hours, the reaction mixture was reacted with saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to give 92.7mg of product, 73.4% yield, 96.8% HPLC purity.
Example 43- (cyclohexylthio) -1-methyl-6-nitroquinolin-2 (1H) -one (I-d)
In a 50mL open round bottom flask equipped with a magnetic stir bar was added compound (II) 1-methyl-6-nitroquinoxalin-2-one (82 mg, 0.4 mmoL), eosin Y (12.9 mg, 0.02 mmoL), cyclohexanethiol (232.4 mg, 2mmoL), acetic acid (48 mg, 0.8mmoL), acetonitrile (5 mL) was added to the mixture, the reaction was stirred for 24 hours at 25 ℃ with 3W blue light irradiation, the reaction mixture was saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO 4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to give 102.7mg of product in 80.5% yield with HPLC purity 98.4%.
Example 53- (heptylthio) -1,6, 7-trimethylquinolin-2 (1H) -one (I-e)
In a 50-part equipped with a magnetic stirring rodA mL open round bottom flask was charged with compound (II) 1,6, 7-trimethylquinoxalin-2-one (75.2 mg, 0.4 mmol), methylene blue (12.8 mg, 0.04 mmol), heptanethiol (1058.4 mg, 8mmol), sulfuric acid (117.6 mg, 1.2mmol), the mixture was irradiated with 3W of blue light, stirred at 25 ℃ for 20 hours, the reaction mixture was reacted with saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to give 116.3mg of product in 91.4% yield with HPLC purity 98.2%.
EXAMPLE 61-methyl-3- (tetradecylthio) quinoxalin-2 (1H) -one (I-f)
In a 50mL open round bottom flask equipped with a magnetic stir bar was added compound (II) 1-methylquinoxalin-2-one (64 mg, 0.4 mmol), rhodamine 6G (19.2 mg, 0.04 mmol), tetradecylthiol (1382.4 mg, 6 mmol), trifluoroacetic acid (91 mg), the mixture was irradiated with 3W of blue light, the reaction was stirred at 30 ℃ for 10 hours, the reaction mixture was reacted with saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to give 81.2mg of product in 52.3% yield with HPLC purity 96.7%.
EXAMPLE 71-methyl-3- (phenethylthio) quinoxalin-2 (1H) -one (I-g)
In a 50mL open round bottom flask equipped with a magnetic stir bar was added compound (II) 1-methylquinoxalin-2-one (64 mg, 0.4 mmol), rhodamine 6G (9.6 mg, 0.02 mmol), phenethyl thiol (1105.8 mg, 8mmol), trifluoromethanesulfonic acid (180 mg, 1.2mmol), the mixture was irradiated with 3W of blue light, the reaction was stirred at 40 ℃ for 24 hours, the reaction mixture was reacted with saturated NaHCO310ml of aqueous solution was quenched and washed with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to give 94.2mg of product, yield 79.6%,HPLC purity 98.8%.
Example 82 Ethyl- ((4-methyl-3-oxo-3, 4-dihydroquinoxalin-2-yl) thio) acetate (I-h)
In a 50mL open round bottom flask equipped with a magnetic stir bar was added compound (II) 1-methylquinoxalin-2-one (64 mg, 0.4 mmol), eosin Y (25.8 mg, 0.04 mmol), ethyl thioglycolate (721.0 mg, 8mmol), sulfuric acid (117.6 mg, 1.2mmol), DMF (5 mL) was added to the mixture, irradiated with 3W of blue light, the reaction was stirred at 35 ℃ for 20 h, the reaction mixture was reacted with saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to give 83.8mg of product in 75.4% yield with an HPLC purity of 97.2%.
Example 93- ((3-mercaptopropyl) thio) -1-methylquinolin-2 (1H) -one (I-I)
In a 50mL open round bottom flask equipped with a magnetic stir bar was added compound (II) 1-methylquinoxalin-2-one (64 mg, 0.4 mmol), rhodamine 6G (38.4 mg, 0.08 mmol), propanedithiol (216.4 mg, 2mmol), acetic acid (72 mg, 1.2mmol), the mixture was dissolved in toluene (5 mL), irradiated with 3W of blue light, the reaction was stirred at 25 ℃ for 18 hours, the reaction mixture was treated with saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to give 39.5mg of product in 37.2% yield with HPLC purity 96.5%.
Example 103- (allylsulfanyl) -1-methylquinolin-2 (1H) -one (I-j)
In a 50mL open round bottom flask equipped with a magnetic stir bar were added compound (II) 1-methylquinoxalin-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, 0.8mmol), toluene (5 mL) was added to the mixture, irradiated with 3W of blue light, and the reaction was stirred at 25 ℃ for 24 hours,the reaction mixture was washed with saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to give 41.5mg of product in 44.7% yield with HPLC purity 98.2%.
Example 117-bromo-3- (ethylsulfanyl) -1-methylquinolin-2 (1H) -one (I-a)
In a 50mL open round bottom flask equipped with a magnetic stir bar was added compound (II) 7-bromo-1-methylquinoxalin-2-one (95.2 mg, 0.4 mmol), ethanethiol (124.3 mg, 2mmol), trifluoroacetic acid (91 mg, 0.8mmol), the mixture was dissolved in DMF (5 mL), the reaction was stirred at 25 ℃ for 24 hours under 3W blue light irradiation, the reaction mixture was saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to obtain 82.92mg of the product 7-bromo-3- (ethylsulfanyl) -1-methylquinolin-2 (1H) -one (I-a), 69.8% yield, 97.6% purity by HPLC.
Example 126-bromo-3- (isopropylsulfanyl) -1-methylquinolin-2 (1H) -one (I-b)
In a 50mL open round bottom flask equipped with a magnetic stir bar was added compound (II) 6-bromo-1-methylquinoxalin-2-one (95.2 mg, 0.4 mmol), isopropylmercaptan (304.6 mg, 4 mmol), acetic acid (48 mg, 0.8mmol), DMSO (5 mL) was added to the mixture, the reaction was stirred at 10 ℃ for 16 hours under irradiation with 3W blue light, the reaction mixture was saturated NaHCO3Quenching with aqueous solution and washing with water. The mixture was extracted with ethyl acetate, and the combined organic layers were extracted with anhydrous Na2SO4Dried and concentrated under reduced pressure. The crude product was purified on a silica gel column using n-hexane/ethyl acetate to give 85.4mg of product in 68.5% yield with HPLC purity 98.6%.
Claims (8)
1. A synthesis method of 3-alkylthio substituted quinoxalinone derivatives is characterized in that quinoxaline-2-ketone compounds shown in a formula (II), thiol compounds shown in a formula (III) and additives are added into an organic solvent according to a certain proportion, the mixture is stirred and reacts for 6-30 hours at 10-40 ℃ under the irradiation of a light source in the presence or absence of a photocatalyst, TLC (thin layer chromatography) is followed until the reaction of the quinoxaline-2-ketone compounds serving as raw materials is completely finished, and the target compound 3-alkylthio substituted quinoxalinone derivatives shown in the formula (I) are obtained through post-treatment;
；
wherein: r1Is C2 ~ C14 alkyl, phenethyl, 3-mercaptopropyl or allyl, R2Is hydrogen, methyl, halogen or nitro, the substituent R2Mono-or di-substituted independently or in any combination.
2. The method for synthesizing 3-alkylthio-substituted quinoxalinone derivatives according to claim 1, characterized in that said additive is cesium carbonate, potassium carbonate, trifluoroacetic acid, trifluoromethanesulfonic acid, sulfuric acid or acetic acid, preferably trifluoroacetic acid, trifluoromethanesulfonic acid, sulfuric acid or acetic acid.
3. The method for synthesizing 3-alkylthio substituted quinoxalinone derivatives according to claim 1, characterized in that said photocatalyst is Ru (bpy)3Cl3、Ir(ppy)3Rose bengal, eosin Y, methylene blue or rhodamine 6G, preferably eosin Y, methylene blue or rhodamine 6G.
4. The method for synthesizing 3-alkylthio substituted quinoxalinone derivatives according to claim 1, characterized in that said organic solvent is selected from one or a combination of any of the following: acetonitrile, DMF, toluene, thiols and DMSO, wherein the feeding amount of the organic solvent and the feeding ratio of the quinoxaline-2-ketone compound shown in the raw material formula (II) are 1.0: 5.0-30, preferably 1.0: 5.0-25, wherein the mercaptan is selected from ethanethiol, tert-butylthiol, heptanethiol or phenethyl thiol.
5. The method for synthesizing 3-alkylthio substituted quinoxalinone derivatives according to claim 1 wherein the light source is blue light, white light or green light, preferably blue light.
6. The method for synthesizing 3-alkylthio substituted quinoxalinone derivatives according to claim 1, wherein the mass ratio of the quinoxaline-2-one compound, the thiol compound, the additive and the photocatalyst is 1.0: 5.0-30: 2.0-4.0: 0.01 to 0.3, preferably 1.0: 5.0-25: 2.0-3.0: 0.01 to 0.2.
7. The method for synthesizing 3-alkylthio-substituted quinoxalinone derivatives according to claim 1, characterized in that the reaction time is 6 to 30 hours; the reaction temperature is 10-40 ℃.
8. The method for synthesizing 3-alkylthio-substituted quinoxalinone derivatives according to claim 1, characterized in that the developing solvent for TLC tracing is a mixture of 5: 1 petroleum ether and ethyl acetate.
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| CN113603651A (en) * | 2021-08-04 | 2021-11-05 | 浙江树人学院（浙江树人大学） | Method for preparing 3-sulfur substituted quinoxalinone derivatives by catalysis |
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| CN110105293A (en) * | 2019-06-14 | 2019-08-09 | 浙江工业大学 | A kind of synthetic method of C-3 difluoromethyl substituted quinoxaline ketones derivant |
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| JIADI ZHOU等: "(Thio)etherification of Quinoxalinones under Visible-Light Photoredox Catalysis", 《ADV. SYNTH. CATAL》 * |
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| CN113603651A (en) * | 2021-08-04 | 2021-11-05 | 浙江树人学院（浙江树人大学） | Method for preparing 3-sulfur substituted quinoxalinone derivatives by catalysis |
| CN113603651B (en) * | 2021-08-04 | 2022-12-13 | 浙江树人学院（浙江树人大学） | Method for preparing 3-sulfur substituted quinoxalinone derivatives by catalysis |
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