Synthesizing method for gamma-pyrone compound

A technology for pyrone and compound, which is applied in the field of organic chemistry synthesis methodology, and can solve the problems of narrow application range of substrates, difficult availability of raw materials and the like

Inactive Publication Date: 2016-07-20
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing synthetic methods mainly use the cyclization reaction of carbonyl compounds to obtain γ-pyrone, and there are certain limitations, such as the difficulty of obtaining raw materials, the use of expensive transition metals, and the narrow scope of substrate application.

Method used

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  • Synthesizing method for gamma-pyrone compound
  • Synthesizing method for gamma-pyrone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Example 1: Reaction of 3-phenylpropiolic acid and ethyl acetoacetate

[0012] 51 mg (0.35 mmol) of 3-phenylpropiolic acid, 91 mg (0.7 mmol) of ethyl acetoacetate, 85 mg (0.525 mmol) of N, N'-carbonyldiimidazole shown in formula III, and 4 -Dimethylaminopyridine 47mg (0.385mmol), sodium hydroxide 28mg (0.7mmol), scandium trifluoromethanesulfonate 30mg (0.07mmol) and 1,2-dichloroethane 2mL were placed in a 25mL two-necked bottle, at 80 Reaction at ℃ for 5-6h, cooling and concentrating the reaction liquid, eluting with a mixed solvent of petroleum ether: ethyl acetate ratio of 5:1 as eluent column chromatography, collecting the eluate of all detected products 58 mg of the product was obtained after the solvent was removed by rotary evaporation, and the yield was 65%.

[0013] Whitesolid, mp: 105-106°C. 1 HNMR (300MHz, CDCl 3 ): δ7.74(d, J=6.3Hz, 2H), 7.44-7.54(m, 3H), 6.77(s, 1H), 4.40(q, J=6.9Hz, 2H), 2.49(s, 3H) , 1.38(t, J=6.9Hz, 3H). 13 CNMR (75MHz, CDCl 3 ): δ17...

Embodiment 2

[0014] Example 2: Reaction of 3-phenylpropiolic acid and methyl acetoacetate

[0015] 51 mg (0.35 mmol) of 3-phenylpropiolic acid, 81 mg (0.7 mmol) of methyl acetoacetate, 85 mg (0.525 mmol) of N, N'-carbonyldiimidazole shown in formula III, and 4 -Dimethylaminopyridine 47mg (0.385mmol), sodium hydroxide 28mg (0.7mmol), scandium trifluoromethanesulfonate 30mg (0.07mmol) and 1,2-dichloroethane 2mL were placed in a 25mL two-necked bottle, at 80 Reaction at ℃ for 5-6h, cooling and concentrating the reaction liquid, eluting with a mixed solvent of petroleum ether: ethyl acetate ratio of 5:1 as eluent column chromatography, collecting the eluate of all detected products Partially, 47 mg of the product was obtained after the solvent was removed by rotary evaporation, and the yield was 51%.

[0016] Whitesolid, mp: 130-131°C. 1 HNMR (500MHz, CDCl 3 ): δ7.75(d, J=6.7Hz, 2H), 7.47-7.54(m, 3H), 6.81(s, 1H), 3.93(s, 3H), 2.51(s, 3H). 13 CNMR (75MHz, CDCl 3 ): δ175.8, 166.2, 165.1, 1...

Embodiment 3

[0017] Example 3: Reaction of 3-phenylpropiolic acid and tert-butyl acetoacetate

[0018] 51 mg (0.35 mmol) of 3-phenylpropiolic acid, 111 mg (0.7 mmol) of tert-butyl acetoacetate, 85 mg (0.525 mmol) of N, N'-carbonyldiimidazole shown in formula III, and 85 mg (0.525 mmol) of N, N'-carbonyldiimidazole shown in formula IV 47mg (0.385mmol) of 4-dimethylaminopyridine, 28mg (0.7mmol) of sodium hydroxide, 30mg (0.07mmol) of scandium trifluoromethanesulfonate and 2mL of 1,2-dichloroethane were placed in a 25mL two-necked bottle, and React at 80°C for 5-6h, cool and concentrate the reaction solution, and elute through column chromatography using a mixed solvent of petroleum ether: ethyl acetate at a ratio of 5:1 as the eluent, and collect all the eluted products detected. The liquid part was evaporated to remove the solvent to obtain 40mg of the product with a yield of 41%.

[0019] Whitesolid, mp: 145-146°C. 1 HNMR (300MHz, CDCl 3 ): δ7.71-7.74(m, 2H), 7.42-7.51(m, 3H), 6.72(s, 1...

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Abstract

The invention relates to the field of organic chemistry, in particular to a synthesizing method for a gamma-pyrone compound. The synthesizing method comprises the steps that acetylenic acid shown in the formula I and a carbonyl compound shown in the formula II serve as raw materials; under the existence of N,N'-carbonyldiimidazole shown in the formula III, 4-dimethylaminopyridine shown in the formula IV, scandium trifluoromethanesulfonate and sodium hydroxide, a reaction is carried out for 5-6 h at 80 DEG C with 1,2-dichloroethane as a solvent, a reaction solution is cooled and condensed, column chromatographic elution is carried out with a mixed solvent with the volume ratio of petroleum ether to ethyl acetate being 5:1, eluant parts of all detected products are collected, the solvent is removed through rotary evaporation, and then the gamma-pyrone product is obtained. The synthesizing method has the advantages that the primer application range is wide, operation is easy and convenient, the reaction is mild, and raw materials and reagents are simple and easy to obtain.

Description

(1) Technical field [0001] The invention relates to a synthesis method of a gamma-pyrone compound, which belongs to the field of organic chemistry synthesis methodology. (2) Background technology [0002] The γ-pyrone skeleton widely exists in natural products and drug molecules with important biological activities (Org. Lett., 2008, 10, 3397; J. Nat. Prod., 2011, 74, 1959.). Therefore, the synthesis of γ-pyrone has aroused the interest of many synthetic chemists. However, the existing synthetic methods mainly use the cyclization reaction of carbonyl compounds to obtain γ-pyrone, and there are certain limitations, such as the difficulty of obtaining raw materials, the use of expensive transition metals, and the narrow scope of substrate application. Therefore, it is very necessary to develop a general, convenient, and simple and easy-to-obtain method for preparing such compounds. (3) Contents of the invention [0003] The object of the present invention is to provide a s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/38C07D407/04
CPCC07D309/38C07D407/04
Inventor 杜鼎董书顶
Owner CHINA PHARM UNIV
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