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Method for synthesizing alpha-pyrone compound

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of complex raw materials, lengthy steps, troublesome operation, etc., and achieve the effects of simple operation, consistent reaction conditions and high conversion rate.

Active Publication Date: 2022-01-14
西安宇特邦医药科技有限公司
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  • Abstract
  • Description
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Problems solved by technology

Previously reported synthetic methods for α-pyrone have limitations such as lengthy steps, complex raw materials, cumbersome operations, high temperature conditions or expensive metal catalysts.

Method used

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  • Method for synthesizing alpha-pyrone compound
  • Method for synthesizing alpha-pyrone compound
  • Method for synthesizing alpha-pyrone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Under nitrogen, diphenylcyclopropenone (0.2mmol), 2-bromo-1-4-(trifluoromethoxy) phenylethanone (0.3mmol), DMAP (20mol%), KOH (0.3 mmol), was added to 100mg of 4A molecular sieves (the purpose was to remove water, and the reaction was controlled under anhydrous conditions) and 1,4-dioxane (2.0mL), and it was heated at 60°C for 12h, After completion of the reaction, cooling to room temperature, filtration, concentration of the reaction mixture by vacuum distillation and purification by flash column chromatography (silica gel, mixture of petroleum ether / ethyl acetate, 20:1, v / v) afforded the desired pure product 67.3 mg, the yield is 82%, and the product is a yellow solid with a melting point of 134-136°C. Its structural formula is:

[0039]

[0040] 1 H NMR (400MHz, CDCl 3 )(δ,ppm):7.93(d,J=8.9Hz,2H,Ar-H),7.38–7.13 (m,13H,Ar-H),6.82(s,1H,Ar-H).

[0041] 13 C{1H}NMR (400MHz, CDCl 3 ;δ, ppm): 162.4, 156.7, 152.5, 150.7, 137.5, 133.5, 130.8, 129.8, 128.8, 128.6, 12...

Embodiment 2

[0045] According to the method described in Example 1, the difference is that the substrates used are: diphenylcyclopropenone (0.2mmol), 2-bromo-1-4-(trifluoromethyl)phenylethanone (0.3mmol), DMAP (20mol%), KOH (0.3mmol), 100 mg of 4A molecular sieves and 1,4-dioxane (2.0mL) yielded 59.5 mg of product with a yield of 76%. The product was a yellow solid with a melting point of 170 ~172°C. Its structural formula is:

[0046]

[0047] 1 H NMR (400MHz, CDCl 3)(δ,ppm):8.03(d,J=8.2Hz,2H,Ar-H),7.74(d,J=8.3Hz,2H,Ar-H),7.32–7.15(m,10H,Ar-H ),6.93(s,1H,Ar-H).

[0048] 13 C{1H}NMR (400MHz, CDCl 3 ;δ, ppm): 162.2, 156.3, 152.2, 137.3, 134.5, 133.4, 130.7, 128.9, 128.6, 128.4, 1278.0 128.0, 126.0, 125.9, 125.7, 124.3, 106.3.

[0049] IRν max (neat):1697,1537,1329,1160,1117,1072,831,789,699cm -1 .

[0050] HRMS (ESI) calcd for C 24 h 15 f 3 o 2 [M+H]+:393.1097,found:393.1100

Embodiment 3

[0052] According to the method described in Example 1, the difference is that the substrates used are: diphenylcyclopropenone (0.2mmol), 2-bromo-1-cyclohexyl ethyl ketone (0.3mmol), DMAP (20mol%), KOH ( 0.3mmol), the heating temperature was 65°C, 100mg of 4A molecular sieve and 1,4-dioxane (2.0mL) gave 27.8mg of the product, the yield was 42%, the product was a white solid, and the melting point was 124~125°C . Its structural formula is:

[0053]

[0054] 1 H NMR (400MHz, CDCl 3 )(δ,ppm):7.25–7.07(m,10H,Ar-H),6.13(s,1H,Ar-H),2.49(t,J=11.6Hz,1H,CH),2.07(d,J =13.2Hz,2H,CH 2 ), 1.86 (d, J=12.9 Hz, 2H, CH 2 ), 1.75 (d, J=15.2Hz, 1H, CH 2 ),1.57–1.18(m,5H,CH 2 ).

[0055] 13 C{1H}NMR (400MHz, CDCl 3 ;δ,ppm): 167.89, 163.63, 152.84, 137.97, 134.10, 130.93, 128.77, 128.64, 128.32, 128.02, 127.57, 122.18, 104.50, 42.32, 30.65, 25.87.

[0056] IRν max (neat):2929,2853,1699,1634,1538,944,764,606,564cm -1 .

[0057] HRMS (ESI) calcd for C 23 h 22 o 2 [M+H]+:331.1693,f...

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Abstract

The invention relates to an alpha-pyrone compound and a synthesis method thereof. According to the novel method for efficiently synthesizing the alpha-pyrone compound, bromoacetophenone and cyclopropenone are catalyzed by DMAP to be subjected to a [3 + 3] cyclization reaction under the alkaline heating condition to generate the alpha-pyrone compound. The method is easy to operate and easily available in raw materials, and has potential economic benefits. Because the alpha-pyrone medicine is widely applied clinically, the provided new method for synthesizing the alpha-pyrone compound and is expected to provide a new direction for clinical application of pyrone. The synthesis method disclosed by the invention has the advantages of simple operation, easily available raw materials, mild reaction conditions, no need of a metal catalyst and easy separation and purification of the product, solves the technical difficulties of complex steps and complex raw materials of the synthesis method in the prior art, is a breakthrough of the existing synthesis technology, and has a very high application value.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing α-pyrone compounds. Background technique [0002] Pyrone is a ketone derivative of pyran, and pyrone derivatives are widely found in nature, mainly in plants. For example, benzopyran (chromene), chromone, coumarin, flavone, isoflavone, anthocyanin and other substances can be regarded as derivatives of pyrone. Pyrone has two isomers divided into α-pyrone and γ-pyrone. α-pyrone is a six-membered cyclic unsaturated lactone that widely exists in many natural products, and in It is widely used in medicine, pesticides, spices, dyes and other fields. α-pyrone also has good biological activity, and α-pyrone is also an important intermediate in organic synthesis. Its conjugated diene structure is more prone to Diels-Alder reaction. [0003] Because of the special structure of α-pyrone, its synthesis has become a research hotspot at home ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/38
CPCC07D309/38Y02P20/55
Inventor 徐四龙张科强乔丽娟
Owner 西安宇特邦医药科技有限公司
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