CN114835664A - Novel trans-styryl benzofuranone compound and efficient synthesis method thereof - Google Patents
Novel trans-styryl benzofuranone compound and efficient synthesis method thereof Download PDFInfo
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- CN114835664A CN114835664A CN202210297813.6A CN202210297813A CN114835664A CN 114835664 A CN114835664 A CN 114835664A CN 202210297813 A CN202210297813 A CN 202210297813A CN 114835664 A CN114835664 A CN 114835664A
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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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Abstract
The invention discloses a novel trans-styryl benzofuranone compound and an efficient synthesis method thereof. The method has the advantages of low cost, high yield, simple and convenient operation, no pollution and the like, and has potential industrial application prospect. The method provides a cheap and green way for preparing the trans-styryl benzofuranone compound.
Description
[ technical field ] A method for producing a semiconductor device
The invention relates to a novel trans-styryl benzofuranone compound and an efficient synthesis method thereof, belonging to the field of organic synthesis. The reaction process has simple conditions and excellent yield, and uses a copper catalyst to alkenyl the benzofuranone into the styrene compound.
[ background of the invention ]
The olefin compounds are important fine chemical intermediates, and can be widely applied to the fields of pesticides, organic functional materials, medicines and the like. The main methods for synthesizing the complex olefin compounds include Heck reaction, Wittig reaction, elimination reaction and the like. However, these reactions have certain disadvantages, such as the Heck reaction requires the use of an acidA noble palladium catalyst, and poor reaction efficiency and stereoselectivity, etc. The benzofuranone is a drug molecular framework and has wide application in the field of organic synthesis. 1,2 The method for synthesizing the olefin compound by taking the benzofuranone as the initial raw material has the advantages of easily obtained raw materials, simple operation, simple reaction conditions, high product yield and purity and the like. The method has the advantages of easily available raw materials, simple operation, mild reaction conditions, high product yield and purity and less synthesis process reports. The synthesized novel benzofuran ketone derivative containing carbon-carbon double bonds has better biological activity and physicochemical properties and higher pharmaceutical value.
[ summary of the invention ]
The invention aims to provide a trans-styryl benzofuranone compound III and a preparation method thereof, namely a novel method for efficiently and selectively synthesizing the trans-styryl benzofuranone compound by using elemental iodine as an oxidant and benzofuranone and styrene as raw materials. The method is characterized in that: CuBr is used as a catalyst, elemental iodine is used as an oxidant, a benzofuranone derivative I and a styrene derivative II are used as reaction raw materials, effective reaction is carried out at 80-150 ℃ under the condition that polar solvents such as acetonitrile and the like are used as solvents, and a trans-styryl benzofuranone compound III can be obtained within 6-18 h.
Wherein said R 1 Is a functional group such as hydrogen, ethyl, dimethyl, fluorine, etc., R 2 Is a functional group such as hydrogen, chlorine, etc., R 3 Is a functional group such as hydrogen, methyl, fluorine, chlorine, bromine, trifluoromethyl, tertiary butyl, methoxycarbonyl and the like.
In the synthesis method, the dosage of the catalyst CuBr is 0.1-1 equivalent, the dosage of the oxidant is 0.5-1.5 equivalent, and the solvent is a polar solvent such as acetonitrile, preferably acetonitrile; the reaction time is 6-18h, preferably 12h, and the reaction temperature is 80-150 ℃, preferably 120 ℃.
The synthesis method of the novel trans-styryl benzofuranone compound catalyzed by CuBr provided by the invention opens up a new low-cost simple way, and has the advantages that: the yield of the target product is high, the reaction condition is simple, and the reaction operation is simple and convenient.
Principle of reaction
[ description of the drawings ]
FIG. 1 is a schematic diagram of a process for preparing novel trans-styryl benzofuranones
[ detailed description ] embodiments
The invention provides a high-efficiency catalytic synthesis method of novel trans-styryl benzofuranone compounds, which is shown in the attached drawing: placing benzofuranone, styrene and oxidant simple substance iodine into a reaction container, reacting for 12 hours in a nitrogen environment at 120 ℃, and performing column separation after the reaction is finished to obtain a target product. The invention is further illustrated below with reference to specific preparation examples:
conditional screening
Example 1:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 H), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogenphosphate and 1ml of acetonitrile, and the reaction was stirred at 120 ℃ for 12H. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 H) to yield a white powderFinally, the yield was 58%.
Characterization data: 1 H NMR(400MHz,Chloroform-d)δ7.38(d,J＝7.0Hz,2H),7.36-7.27(m,7H), 7.23(s,1H),7.18-7.07(m,2H),7.05(s,1H),6.64-6.52(m,2H),2.36(s,3H). 13 C{ 1 H}NMR (101MHz,Chloroform-d)δ176.4,150.9,139.3,136.0,134.4,132.8,130.0,129.9,129.1,128.8, 128.4,128.2,127.9,127.5,126.9,126.2,111.0,58.7,21.4.HRMS(EI)m/z:[M+H] + calcd for C 23 H 19 O 2 327.1385Found 327.1389.
example 2:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 H), 0.2mmol, cuprous bromide 0.2mmol, disodium hydrogenphosphate 0.4mmol, and acetonitrile 1ml, and the reaction was stirred at 120 ℃ for 12H. After the reaction is finished, no target product exists.
Example 3:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 H), iodine 0.2mmol, disodium hydrogenphosphate 0.4mmol, and acetonitrile 1ml, and the reaction was stirred at 120 ℃ for 12 hours. After the reaction is finished, no target product exists.
Example 4:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 4-methyl), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction is stirred at 120 ℃ for 12 h. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 4-methyl) to give a white powder with a yield of 83%.
Example 5:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 4-fluoro), 0.2mmol, cuprous bromide 0.2mmol, iodine 0.2mmol, and hydrogen phosphate dibasicSodium 0.4mmol and acetonitrile 1ml, the reaction was stirred at 120 ℃ for 12 h. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 4-fluoro) to give a white powder in 67% yield.
Example 6:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 4-chloro), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction was stirred at 120 ℃ for 12 hours. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 4-chloro) to give a white powder with a yield of 60%.
Example 7:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 4-bromo), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction is stirred at 120 ℃ for 12 hours. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 4-bromo) to give a white powder in 53% yield.
Example 8:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 4-trifluoromethyl), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction is stirred at 120 ℃ for 12 h. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 4-trifluoromethyl) to give a white powder in 58% yield.
Example 9:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 4-tert-butyl), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction was stirred at 120 ℃ for 12 h. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 4-tert-butyl) to give a white powder in 94% yield.
Example 10:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 4-methoxycarbonyl), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction was stirred at 120 ℃ for 12 hours. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 4-methoxycarbonyl) to yield a white powder with a yield of 37%.
Example 11:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 3-methyl), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction is stirred at 120 ℃ for 12 h. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 3-methyl) to give a white powder with a yield of 89%.
Example 12:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 = 3-bromo), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction was stirred at 120 ℃ for 12 hours. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 3-bromo) to give a white powder in 89% yield.
Example 13:
the benzofuranone derivative was added to a 10mL reaction tubeI(R 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 3-trifluoromethyl), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction is stirred at 120 ℃ for 12 h. After the reaction is finished, a target compound III (R) is obtained through column chromatography separation 1 4-methyl, R 2 ＝H，R 3 3-trifluoromethyl) to give a white powder in 58% yield.
Example 14:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-methyl, R 2 H)0.2mmol, styrene derivative II (R) 3 2-bromo), cuprous bromide 0.2mmol, iodine 0.2mmol, disodium hydrogen phosphate 0.4mmol and acetonitrile 1ml, and the reaction was stirred at 120 ℃ for 12 h. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-methyl, R 2 ＝H，R 3 2-bromo) to give a white powder in 39% yield.
Example 15:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 ＝H，R 2 H)0.2mmol, styrene derivative II (R) 3 4-tert-butyl), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction was stirred at 120 ℃ for 12 h. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 ＝H，R 2 ＝H，R 3 4-tert-butyl) to give a white powder with a yield of 89%.
Example 16:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 4-ethyl, R 2 H)0.2mmol, styrene derivative II (R) 3 4-tert-butyl), 0.2mmol of cuprous bromide, 0.2mmol of iodine, 0.4mmol of disodium hydrogen phosphate and 1ml of acetonitrile, and the reaction was stirred at 120 ℃ for 12 h. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 4-ethyl, R 2 ＝H，R 3 4-tert-butyl) to give a white powder with a yield of 86%.
Example 17:
the benzofuranone derivative I (R) was added to a 10mL reaction tube 1 3, 5-dimethyl, R 2 H)0.2mmol, styrene derivative II (R) 3 2-tert-butyl), cuprous bromide 0.2mmol, iodine 0.2mmol, disodium hydrogen phosphate 0.4mmol and acetonitrile 1ml, and the reaction is stirred at 120 ℃ for 12 h. After the reaction is finished, the target compound III (R) is obtained by column chromatography separation 1 3, 5-dimethyl, R 2 ＝H，R 3 4-tert-butyl) to give a white powder in 88% yield.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent should be defined by the appended claims.
Reference:
1. qinrua, child boat, Tangzhi, xuwisdom, a high-efficiency catalytic synthesis method of 2-hydroxybenzophenones, CN 109534975B.
2. Qiren Hua, Tangzhi, Tongshan, xuanwis, a class of benzofuran triarylmethane compounds and their green catalytic synthesis, CN 109651344A.
Claims (2)
1. A novel trans-styryl benzofuranone compound III and an efficient synthesis method thereof are characterized in that CuBr is used as a catalyst, an iodine simple substance is used as an oxidant, disodium hydrogen phosphate is used as an alkali, benzofuranone I and styrene II are used as reaction raw materials, the temperature is increased under the condition of nitrogen to effectively react, and the trans-styryl benzofuranone III with high yield can be obtained within a certain time.
WhereinThe R is 1 Is a functional group such as hydrogen, ethyl, dimethyl, fluorine, etc., R 2 Is a functional group such as hydrogen, chlorine, etc., R 3 Is a functional group such as hydrogen, methyl, fluorine, chlorine, bromine, trifluoromethyl, tertiary butyl, methoxycarbonyl and the like.
2. The synthesis process according to claim 1, characterized in that the catalyst CuBr is used in an amount of 0.1-1 equivalent, the oxidant in an amount of 0.5-1.5 equivalent, the solvent is a polar solvent, preferably acetonitrile; the reaction time is 6-18h, preferably 12h, and the reaction temperature is 80-150 ℃, preferably 120 ℃.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116768756A (en) * | 2023-05-30 | 2023-09-19 | 湖南大学 | Novel 2-hydroxy diaryl methane compound and efficient synthesis method thereof |
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| CN101665477A (en) * | 2009-09-21 | 2010-03-10 | 四川大学 | (E)-3-(benzfuran-5-yl) acrylic ester compound, preparation method and application thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116768756A (en) * | 2023-05-30 | 2023-09-19 | 湖南大学 | Novel 2-hydroxy diaryl methane compound and efficient synthesis method thereof |
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