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Method for synthesizing multi-substituted chromone compound

A chromone compound, multi-substitution technology, applied in the direction of organic chemistry, etc., can solve the problems of restricting the synthesis and development of multi-substitution chromone compounds, difficult to prepare, etc.

Active Publication Date: 2012-03-21
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the literature, such compounds are mainly prepared by the acid-catalyzed intramolecular condensation reaction of 1,3-diketone compounds, but the precursors of this method are not easy to prepare, and harsh conditions such as strong acid and high temperature are required, which limits the ability of multi-substituted chromones. Synthetic Development of Compounds

Method used

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  • Method for synthesizing multi-substituted chromone compound
  • Method for synthesizing multi-substituted chromone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add potassium fluoride (0.0466 g, 0.8 mmol) and 18-crown ether (0.2118 g, 0.8 mmol) to the sealed tube in the glove box; then add 2-methyl-4-phenyl- 2,3-Butadienoic acid (0.0700 g, 0.4 mmol), 2-(trimethylsilyl)phenyl triflate (0.15 mL, d = 1.229 g / ml, 0.1844 g, 0.4 mmol) and tetrahydrofuran (4 ml), after the addition was completed, the tube was sealed and placed in an oil bath at 80 degrees Celsius; after reacting at 80 degrees Celsius for 12 hours, it was returned to room temperature, and the silica gel was short Column filtration, diethyl ether washing; spin drying and flash column chromatography gave 0.0888 g of 3-benzyl-3-methylchromone, the yield was 88%, the product was solid, m.p. 125.7-126.2 o C (hexane / ethyl acetate).

[0026] 1 H NMR (300 MHz, CDCl 3 ) δ 8.19 (dd, J 1 = 8.1 Hz, J 2 = 1.5 Hz, 1 H, Ar-H), 7.64-7.52 (m, 1 H, Ar-H), 7.40-7.20 (m, 7 H, Ar-H), 4.05 (s, 2 H, PhCH 2 ), 2.15 (s, 3 H, CH 3 ); 13 C NMR (CDCl 3 , 75 MHz) δ 178.1, 162.7, 155...

Embodiment 2

[0029] According to the method described in Example 1, the difference is that the amount of reagent used is: potassium fluoride (0.698 g, 12 mmol), 18-crown ether (3.1690 g, 12 mmol), 2-methyl-4-benzene 2,3-butadienoic acid (1.048 g, 6 mmol), 2-(trimethylsilyl)phenyl triflate (2.25 mL, d = 1.229 g / ml, 2.7653 g, 9 mmol), tetrahydrofuran (60 ml), to give 1.3648 g of 3-benzyl-3-methylchromone, yield 91%.

[0030]

Embodiment 3

[0032] According to the method described in Example 1, the difference is that the substrates and reagents used are: potassium fluoride (0.0468 g, 0.8 mmol), 18-crown ether (0.2112 g, 0.8 mmol), 2-methyl-4 -p-methylphenyl-2,3-butadienoic acid (0.0752 g, 0.4 mmol), 2-(trimethylsilyl)phenyl triflate (0.15 mL, d = 1.229 g / ml, 0.1844 g, 0.6 mmol), 0.0955 g of 3-methyl-2-p-methylbenzochromone was obtained, the yield was 90%, and the product was solid, m.p. 102.9-103.3 o C (hexane / ethyl acetate).

[0033] 1 H NMR (300 MHz, CDCl 3 ) δ 8.16 (dd, J 1 = 7.8 Hz, J 2 = 1.5 Hz, 1 H, Ar-H), 7.63-7.53 (m, 1 H, Ar-H), 7.40-7.28 (m, 2 H, Ar-H), 7.17 (d, J = 8.1 Hz, 2 H, Ar-H), 7.12 (d, J = 8.1 Hz, 2 H, Ar-H), 4.00 (s, 2 H, ArCH 2 ), 2.31 (s, 3 H, CH 3 ), 2.15 (s, 3 H, CH 3 ); 13 C NMR (CDCl 3 , 75 MHz) δ 178.3, 163.1, 155.9, 136.6, 133.0, 132.8, 129.4, 128.3, 125.7, 124.5, 122.5, 117.7, 117.3, 37.8, 21.0, 10.1; MS (EI) m / z (%) 264 (M + , 8.78), 61 (100); IR (KBr, cm -1) 29...

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Abstract

The invention relates to a method for synthesizing multi-substituted chromone compounds, which includes a step for generating a series of multi-substituted chromone compounds, namely, enabling 2,3-allenoic acid and benzyne generated on the spot to give an insertion / 1,2-addition / ring opening / 1,4-addition reaction in tetrahydrofuran. The method for synthesizing the multi-substituted chromone compounds is simple in operation, easily obtainable in raw materials and reagent, higher in reaction yield, capable of avoiding the shortcoming of difficulty in preparation and severe conditions of a traditional method precursor, easily separable and purificatory in products, and suitable for synthesizing the multi-substituted chromone compounds.

Description

technical field [0001] The present invention relates to a method for synthesizing various substituted chromones, that is, a series of various substituted chromones are generated in one step through the series reaction of 2,3-alkenoic acid and benzyne generated on the spot in tetrahydrofuran compound. [0002] Background technique [0003] Chromone compounds are a class of compounds with benzo-γ-pyrone as the skeleton, which widely exist in nature in various forms. There are many reports on its physiological and pharmaceutical activities, and it has many uses such as anti-inflammatory, antibacterial, anti-cancer, anti-oxidation, anti-AIDS, anti-allergic, and hypolipidemic, so it has always been a hot spot in medicinal chemistry research. In the literature, such compounds are mainly prepared by the acid-catalyzed intramolecular condensation reaction of 1,3-diketone compounds, but the precursors of this method are not easy to prepare, and harsh conditions such as strong acid ...

Claims

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Application Information

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IPC IPC(8): C07D311/22
Inventor 麻生明柴国璧仇友爱傅春玲
Owner ZHEJIANG UNIV
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